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Thiophene

PubChem CID
8030
Structure
Thiophene_small.png
Thiophene_3D_Structure.png
Molecular Formula
Synonyms
  • THIOPHENE
  • 110-02-1
  • Thiofuran
  • Thiole
  • Thiophen
Molecular Weight
84.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Thiophene appears as a colorless liquid with an unpleasant odor. Insoluble in water and slightly denser than water. Flash point 30 °F. Vapors heavier than air. Irritates the skin, eyes, and mucous membranes. Used to make pharmaceuticals and dyes.
Thiophene is a monocyclic heteroarene that is furan in which the oxygen atom is replaced by a sulfur. It has a role as a non-polar solvent. It is a mancude organic heteromonocyclic parent, a member of thiophenes, a monocyclic heteroarene and a volatile organic compound.
Thiophene has been reported in Solanum lycopersicum, Coffea arabica, and other organisms with data available.
See also: Laboratory-grade xylene (impurity of); Polythiophene (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Thiophene.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

thiophene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C4H4S/c1-2-4-5-3-1/h1-4H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

YTPLMLYBLZKORZ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CSC=C1
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C4H4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

C4H4S

SCH=CHCH=CH

2.3 Other Identifiers

2.3.1 CAS

110-02-1

2.3.3 Deprecated CAS

8014-23-1

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 UN Number

2.3.7 ChEBI ID

2.3.8 ChEMBL ID

2.3.9 DSSTox Substance ID

2.3.10 HMDB ID

2.3.11 ICSC Number

2.3.12 Metabolomics Workbench ID

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Thiophene
  • Thiophenes

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
84.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
84.00337130 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
84.00337130 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
28.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
5
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
22.8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Thiophene appears as a colorless liquid with an unpleasant odor. Insoluble in water and slightly denser than water. Flash point 30 °F. Vapors heavier than air. Irritates the skin, eyes, and mucous membranes. Used to make pharmaceuticals and dyes.
Colorless liquid with a benzene-like odor; [HSDB] Colorless liquid with an odor of "stench"; [MSDSonline]
Liquid
COLOURLESS LIQUID WITH PUNGENT ODOUR.

3.2.2 Color / Form

COLORLESS LIQUID
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 1145

3.2.3 Odor

SLIGHT AROMATIC ODOR RESEMBLING BENZENE
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596

3.2.4 Boiling Point

183.9 °F at 760 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
84.0 °C @ 760 MM HG
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-320
84.00 °C. @ 760.00 mm Hg
The Good Scents Company Information System
84 °C

3.2.5 Melting Point

-36.8 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
-39.4 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-320
-38.3 °C
-38 °C

3.2.6 Flash Point

30 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
30 °F (-1 °C) (CLOSED CUP)
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-87
-1 °C

3.2.7 Solubility

less than 1 mg/mL at 75 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
MISCIBLE IN ETHANOL, ETHER, ACETONE, AND BENZENE.
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-320
SOL IN ALL PROPORTIONS IN ORDINARY ORG SOLVENTS, CARBON TETRACHLORIDE, DIOXANE, PYRIMIDINE, TOLUENE
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-515
water solubility = 3,020 mg/l @ 25 °C
Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth ed, Tucson, AZ: Univ Az, College of Pharmacy (1992)
3.01 mg/mL at 25 °C
Solubility in water: none

3.2.8 Density

1.0649 at 68 °F (NTP, 1992) - Denser than water; will sink
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.06494 @ 20 °C/4 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-320
Relative density (water = 1): 1.06

3.2.9 Vapor Density

2.9 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
2.9 (AIR= 1)
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-87
Relative vapor density (air = 1): 2.9

3.2.10 Vapor Pressure

20 mmHg at 32 °F ; 60 mmHg at 68.2 °F; 760 mmHg at 183.9 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
79.7 [mmHg]
79.7 mm Hg @ 25 °C
Boublik, T., Fried, V., and Hala, E., The Vapour Pressures of Pure Substances. Second Revised Edition. Amsterdam: Elsevier, 1984.
Vapor pressure, kPa at 12.5 °C: 5.3

3.2.11 LogP

log Kow = 1.81
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 8
1.81

3.2.12 Autoignition Temperature

395 °C

3.2.13 Decomposition

WHEN HEATED TO DECOMPOSITION IT EMITS HIGHLY TOXIC FUMES OF SULFUR OXIDES.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 3163
May be heated to 850 °C without decomposition.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596

3.2.14 Viscosity

0.621 mPa.s
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA26 793

3.2.15 Heat of Combustion

-2807 kJ/mol
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA26 793

3.2.16 Heat of Vaporization

32.483 kJ/mol
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA26 793

3.2.17 Refractive Index

INDEX OF REFRACTION: 1.52684 @ 25 °C/D
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596

3.2.18 Kovats Retention Index

Standard non-polar
649 , 658 , 668 , 648 , 650 , 646 , 648 , 668 , 668 , 668 , 670 , 671 , 650 , 648 , 651.8 , 646 , 647 , 647 , 643.23 , 685 , 651 , 657.4 , 650 , 653 , 644 , 645 , 644 , 645 , 665 , 650 , 647 , 655
Semi-standard non-polar
672 , 703 , 661 , 661 , 673 , 665 , 665 , 626 , 671 , 636 , 694 , 674.6 , 679.6 , 686.1 , 700 , 685.3 , 683 , 686 , 694 , 675 , 694 , 664.6 , 685.3 , 641 , 648 , 632 , 644 , 693 , 632 , 644 , 693 , 652 , 690 , 665 , 675 , 680 , 686 , 700 , 665 , 667 , 676.8 , 694 , 680 , 660.4 , 677 , 700 , 693
Standard polar
1022 , 1028 , 1034 , 1030 , 1017 , 1023 , 1028 , 1054 , 1039 , 1023 , 1046 , 1010 , 1024 , 1024 , 1026 , 1035 , 1054 , 1021 , 1021 , 1021 , 1041 , 995 , 1022 , 1035 , 1022 , 1025 , 1018 , 1032 , 1034 , 1032 , 1035 , 1015 , 1016.2 , 1018.5 , 1020 , 1029.9

3.2.19 Other Experimental Properties

CYCLIC ORGANOSULFUR; HIGHLY REACTIVE
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 1145
MAY BE HEATED TO 850 °C WITHOUT DECOMP
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596
hydroxyl radical rate constant = 9.53X10-12 cu m/molc-sec @ 25 °C
Atkinson R; Journal of Physical And Chemical Reference Data. Monograph No 1 (1989)

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Thiophenes

4 Spectral Information

4.1 1D NMR Spectra

1 of 3
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1D NMR Spectra
MAX ABSORPTION (ALCOHOL): 215 NM (LOG E= 3.8); 231 NM (LOG E= 3.87); SADTLER REFERENCE NUMBER: 134 (NMR)
1D NMR Spectra
NMR: 52 (Varian Associates NMR Spectra Catalogue)
2 of 3
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1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 3
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Spectra ID
Instrument Type
JEOL
Frequency
90 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
7.36:236.00, 7.08:602.00, 7.26:99.00, 7.13:406.00, 7.34:415.00, 7.35:316.00, 7.30:1000.00, 7.37:567.00, 7.11:424.00, 7.03:25.00, 7.18:92.00, 7.41:27.00, 7.09:300.00, 7.12:436.00, 7.33:446.00, 7.14:971.00, 7.09:218.00, 7.31:443.00, 7.14:413.00
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Instrument Name
BRUKER AC-300
Source of Sample
Eastman Organic Chemicals, Rochester, New York
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 3
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Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
125.08:1000.00, 126.82:985.00
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Source of Sample
Eastman Organic Chemicals, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 6
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NIST Number
291513
Library
Main library
Total Peaks
43
m/z Top Peak
84
m/z 2nd Highest
58
m/z 3rd Highest
45
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NIST Number
531
Library
Replicate library
Total Peaks
51
m/z Top Peak
84
m/z 2nd Highest
58
m/z 3rd Highest
45
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4.2.2 Other MS

Other MS
MASS: 116 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

4.3 UV Spectra

UV: 68 (Sadtler Research Laboratories Spectral Collection)
Weast, R.C. and M.J. Astle. CRC Handbook of Data on Organic Compounds. Volumes I and II. Boca Raton, FL: CRC Press Inc. 1985., p. V2 343

4.3.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 IR Spectra

IR Spectra
IR: 172 (Sadtler Research Laboratories Prism Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
NEAT
Source of Sample
Matheson Gas Products
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
Layer between KBr
Source of Sample
Fluka
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Technique
ATR-Neat
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
T31801
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Near IR Spectra

1 of 2
Instrument Name
BRUKER IFS 88
Technique
NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=6505,REO=2,CNM=HEI,ZFF=2
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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2 of 2
Instrument Name
BRUKER IFS 88
Technique
NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=6505,REO=2,CNM=HEI,ZFF=2
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.4.4 Vapor Phase IR Spectra

1 of 2
Technique
Vapor Phase
Source of Sample
Pennwalt Corporation
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker IFS 85
Technique
Gas-GC
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.5 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company LLC
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/aldrich/T31801>T31801</a>
Lot Number
SHBD6661V
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Pharmacology and Biochemistry

8.1 Absorption, Distribution and Excretion

RABBITS FED THIOPHEN 150 MG/KG EXCRETED ABOUT 35% OF DOSE UNCHANGED IN EXPIRED AIR & 0.5% IN FECES.
BRAY HG ET AL; BIOCHEM J 109(2) 11 (1968)
(35)S-LABELED THIOPHENE APPLIED TO RABBIT SKIN OR INJECTED IP INTO RATS WAS IMMEDIATELY INCORPORATED INTO SKIN.
BIKBULATOVA LI ET AL; VOPR REAKT ORG NORME PATOL, MATER NAUCHN KONF 23 (1974)
(35)S-LABELED THIOPHENE (250 MUCI) ADMIN ONCE SC TO RATS WAS RAPIDLY ABSORBED INTO BLOOD STREAM, DEPOSITED IN MAJOR ORGANS, & EXCRETED WITH URINE. URINE ANAL SHOWED 61.1% OF ISOTOPE WAS EXCRETED WITHIN 34 HR & 74.4% WITHIN 3 DAYS.
BIKBULATOV NT, NIGMATULLINA GN; SB NAUCHN TR BASHK GOS MED INST 19:114 (1976)
FOLLOWING RECTAL & ORAL ADMIN OF (14)C-LABELED THIOPHENE (33 MG/KG), PULMONARY EXCRETION WAS 40% & 5%, RESPECTIVELY.
CHANAL JL ET AL; EUR J MED CHEM -CHIM THER 9(6) 641 (1974)

8.2 Metabolism / Metabolites

THIOPHEN IS METABOLIZED IN VIVO TO PREMERCAPTURIC ACID AND 2-THIENYL-MERCAPTURIC ACID.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 386
RABBITS FED THIOPHEN 150 MG/KG EXCRETED 40% OF DOSE IN URINE IN FORM OF 2 MERCAPTURIC ACIDS, BELIEVED TO BE THIENYL 3-MERCAPTURIC ACID & THIENYL 2-MERCAPTURIC ACID.
BRAY HG ET AL; BIOCHEM J 109(2) 11 (1968)
MAJOR METABOLITE OF THIOPHENE (200-300 MG/KG, ORALLY) IN RATS & RABBITS WAS 3-HYDROXY-2,3-DIHYDRO-2-THIENYLMERCAPTURIC ACID & 2-THIENYLMERCAPTURIC ACID WAS MINOR METABOLITE. IN RAT 32% OF THIOPHENE EXCRETED UNCHANGED IN EXPIRED AIR & 40% EXCRETED IN URINE AS MERCAPTURIC ACIDS.
BRAY HG ET AL; XENOBIOTICA 1(2) 157 (1971)

8.3 Human Metabolite Information

8.3.1 Cellular Locations

  • Cytoplasm
  • Extracellular

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as a solvent, chemical intermediate, and monomer to make copolymers; [HSDB]
ORGANIC SYNTHESIS; COPOLYMERIZES WITH MALEIC ANHYDRIDE
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 1145
SOLVENT; INT FOR PHARMACEUTICALS, THIOPHENE-PHENOL/FORMALDEHYDE RESINS, AND NEMATOCIDE TETRACHLOROTHIOPHENE
SRI

9.1.1 Use Classification

Hazard Classes and Categories -> Flammable - 3rd degree

9.2 Methods of Manufacturing

MADE AVAILABLE IN COMMERCIAL QUANTITIES BY PROCESS UTILIZING DEHYDROGENATION OF BUTANE WITH SULFUR AS DEHYDROGENATING AGENT, FOLLOWED BY CYCLIZATION WITH SULFUR TO FORM THIOPHENE RING. LAB PREPN BY HEATING SODIUM SUCCINATE WITH PHOSPHORUS TRISULFIDE. ALSO PREPARED BY PASSING ETHYLENE OR ACETYLENE INTO BOILING SULFUR; OR BY PASSING ACETYLENE AND HYDROGEN SULFIDE OVER HOT BAUXITE OR NICKEL HYDROXIDE.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596
FROM...PETROLEUM; SYNTHETICALLY FROM HEATING SODIUM SUCCINATE WITH PHOSPHORUS TRISULFIDE.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 1145

9.3 U.S. Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
SRI
(1975) GREATER THAN 4.54X10+5 GRAMS
SRI

9.4 General Manufacturing Information

EPA TSCA Commercial Activity Status
Thiophene: ACTIVE
THIOPHENE IS A SULFUR-CONTAINING FLAVOR COMPOUND FORMED BY MAILLARD REACTIONS IN HEAT-PROCESSED COFFEE AND BEEF. /FROM TABLE/
Fenaroli's Handbook of Flavor Ingredients. Volume 1. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 145
/THIOPHENE IS A/ SOLVENT SIMILAR TO BENZENE, BUT SUITABLE FOR LOWER & HIGHER TEMPERATURES...
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596
STUDIES WERE CONDUCTED ON DEODORIZATION CATALYSTS. THIOPHENE WAS USED AS MODEL IN LOW CONCN RANGE.
KABE T ET AL; NIPPON KAGAKU KAISHI 3: 349 (1980)
MILK XANTHINE OXIDASE CATALYZED THE OXIDATION OF CROTONALDEHYDE WHEN PRESENT AS A SUSPENSION IN THIOPHENE OR IN OTHER NONPOLAR SOLVENTS.
DASTOLI FR, PRICE S; ARCH BIOCHEM BIOPHYS 118(1) 163 (1967)
FOUND IN COAL TAR, IN COAL GAS & TECHNICAL BENZENE.
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1596

10 Identification

10.1 Analytic Laboratory Methods

ANALYTE: THIOPHENE; MATRIX: AIR; RANGE: 0.05-GREATER THAN 7 MG/CU M; PROCEDURE: ADSORPTION ON CHARCOAL, DESORPTION WITH TOLUENE, GC ANALYSIS.
U.S. Department of Health, Education Welfare, Public Health Service. Center for Disease Control, National Institute for Occupational Safety Health. NIOSH Manual of Analytical Methods. 2nd ed. Volumes 1-7. Washington, DC: U.S. Government Printing Office, 1977-present., p. V1 255-1
PARTITION CONSTANT FOR THIOPHENE IN AQ SOLN WAS DETERMINED BY GAS CHROMATOGRAPHY IN WASTEWATER.
CHALAYA ZI ET AL; ZH ANAL KHIM 30(4) 798 (1975)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

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Note
Pictograms displayed are for 98.3% (349 of 355) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1.7% (6 of 355) of reports.
Pictogram(s)
Flammable
Corrosive
Acute Toxic
Irritant
Signal
Danger
GHS Hazard Statements

H225 (98.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]

H302 (73.5%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (21.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (65.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (39.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (46.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H331 (14.9%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H332 (33.2%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (39.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H412 (52.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 355 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 6 of 355 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 17 notifications provided by 349 of 355 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Flam. Liq. 2 (98.3%)

Acute Tox. 4 (73.5%)

Acute Tox. 4 (21.7%)

Skin Irrit. 2 (65.9%)

Eye Dam. 1 (39.7%)

Eye Irrit. 2A (46.2%)

Acute Tox. 3 (14.9%)

Acute Tox. 4 (33.2%)

STOT SE 3 (39.7%)

Aquatic Chronic 3 (52.7%)

Flammable liquids - Category 2

Skin corrosion/irritation - Category 2

Specific target organ toxicity - Repeated exposure - Category 2 (liver, brain)

Hazardous to the aquatic environment (Acute) - Category 3

Hazardous to the aquatic environment (Long-term) - Category 3

11.1.3 NFPA Hazard Classification

NFPA 704 Diamond
2-3-0
NFPA Health Rating
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
NFPA Fire Rating
3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.
NFPA Instability Rating
0 - Materials that in themselves are normally stable, even under fire conditions.

11.1.4 Health Hazards

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

ERG 2024, Guide 130 (Thiophene)

· May cause toxic effects if inhaled or absorbed through skin.

· Inhalation or contact with material may irritate or burn skin and eyes.

· Fire will produce irritating, corrosive and/or toxic gases.

· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.

· Runoff from fire control or dilution water may cause environmental contamination.

11.1.5 Fire Hazards

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024)

ERG 2024, Guide 130 (Thiophene)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

· Vapors may form explosive mixtures with air.

· Vapors may travel to source of ignition and flash back.

· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).

· Vapor explosion hazard indoors, outdoors or in sewers.

· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.

· Runoff to sewer may create fire or explosion hazard.

· Containers may explode when heated.

· Many liquids will float on water.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

11.1.6 Hazards Summary

Contact can cause redness of the eyes and skin; Inhalation can cause sore throat, cough and dizziness; [ICSC] May be toxic to the liver; [NJ-HSFS] A skin and eye irritant; May cause liver injury; [MSDSonline]

11.1.7 Fire Potential

A VERY DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 3163

11.2 Safety and Hazard Properties

11.2.1 Lower Explosive Limit (LEL)

2.1 % at 63 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.2.2 Upper Explosive Limit (UEL)

17.25 % at 86 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

11.2.3 Critical Temperature & Pressure

Critical temperature: 317 °C; Critical pressure: 4.53X10+6 Pa
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA26 793

11.2.4 Physical Dangers

The vapour is heavier than air and may travel along the ground; distant ignition possible. As a result of flow, agitation, etc., electrostatic charges can be generated.

11.2.5 Explosive Limits and Potential

Explosive limits , vol% in air: 1.5-12.5

11.3 First Aid Measures

Inhalation First Aid
Fresh air, rest. Refer for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse and then wash skin with water and soap.
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth. Rest.

11.3.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
ERG 2024, Guide 130 (Thiophene)

General First Aid:

· Call 911 or emergency medical service.

· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.

· Move victim to fresh air if it can be done safely.

· Administer oxygen if breathing is difficult.

· If victim is not breathing:

-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingestedor inhaled the substance.

-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).

-- If no pulse detected or no respiratory medical device available, provide continuouscompressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.

· Remove and isolate contaminated clothing and shoes.

· For minor skin contact, avoid spreading material on unaffected skin.

· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.

· For severe burns, immediate medical attention is required.

· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.

· Keep victim calm and warm.

· Keep victim under observation.

· For further assistance, contact your local Poison Control Center.

· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.

Specific First Aid:

· Wash skin with soap and water.

· In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin.

11.4 Fire Fighting

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.

SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.

LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.

FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

11.4.1 Fire Fighting Procedures

FOAM, CARBON DIOXIDE, DRY CHEMICAL.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 3163

11.5 Accidental Release Measures

Public Safety: ERG 2024, Guide 130 (Thiophene)

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Keep unauthorized personnel away.

· Stay upwind, uphill and/or upstream.

· Ventilate closed spaces before entering, but only if properly trained and equipped.

Spill or Leak: ERG 2024, Guide 130 (Thiophene)

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· All equipment used when handling the product must be grounded.

· Do not touch or walk through spilled material.

· Stop leak if you can do it without risk.

· Prevent entry into waterways, sewers, basements or confined areas.

· A vapor-suppressing foam may be used to reduce vapors.

· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.

· Use clean, non-sparking tools to collect absorbed material.

Large Spill

· Dike far ahead of liquid spill for later disposal.

· Water spray may reduce vapor, but may not prevent ignition in closed spaces.

11.5.1 Isolation and Evacuation

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area for at least 50 meters (150 feet) in all directions.

LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet).

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Evacuation: ERG 2024, Guide 130 (Thiophene)

Immediate precautionary measure

· Isolate spill or leak area for at least 50 meters (150 feet) in all directions.

Large Spill

· Consider initial downwind evacuation for at least 300 meters (1000 feet).

Fire

· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

11.5.2 Spillage Disposal

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

11.5.3 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

11.6 Handling and Storage

11.6.1 Nonfire Spill Response

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.

LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024)

11.6.2 Safe Storage

Fireproof. Separated from oxidizing materials.

11.7 Exposure Control and Personal Protection

Protective Clothing: ERG 2024, Guide 130 (Thiophene)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

11.7.1 Emergency Response Planning Guidelines

Emergency Response: ERG 2024, Guide 130 (Thiophene)

CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.

Small Fire

· Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.

Large Fire

· Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.

· Avoid aiming straight or solid streams directly onto the product.

· If it can be done safely, move undamaged containers away from the area around the fire.

Fire Involving Tanks, Rail Tank Cars or Highway Tanks

· Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.

· Cool containers with flooding quantities of water until well after fire is out.

· Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.

· ALWAYS stay away from tanks in direct contact with flames.

· For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

11.7.2 Inhalation Risk

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

11.7.3 Effects of Short Term Exposure

The substance is irritating to the eyes and skin.

11.7.4 Personal Protective Equipment (PPE)

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

11.7.5 Preventions

Fire Prevention
NO open flames, NO sparks and NO smoking. NO contact with oxidizing agents. Closed system, ventilation, explosion-proof electrical equipment and lighting. Prevent build-up of electrostatic charges (e.g., by grounding).
Exposure Prevention
PREVENT GENERATION OF MISTS!
Inhalation Prevention
Use ventilation, local exhaust or breathing protection.
Skin Prevention
Protective gloves.
Eye Prevention
Wear safety goggles or eye protection in combination with breathing protection.
Ingestion Prevention
Do not eat, drink, or smoke during work.

11.8 Stability and Reactivity

11.8.1 Air and Water Reactions

Highly flammable. Insoluble in water.

11.8.2 Reactive Group

Hydrocarbons, Aromatic

Sulfides, Organic

11.8.3 Reactivity Alerts

Highly Flammable

11.8.4 Reactivity Profile

THIOPHENE reacts violently with strong oxidizing agents and concentrated nitric acid causing fire and explosion hazards [Handling Chemicals Safely 1980. p. 899]. A mixture of thiophene and N-nitrosoacetanilide exploded at 0 °C [Ber., 1887, 30, 367].

11.8.5 Hazardous Reactivities and Incompatibilities

Explosive reaction with N-nitrosoacetanilide. Violent or explosive reaction with nitric acid. Incompatible with oxidizing materials.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 3163

11.9 Transport Information

11.9.1 DOT Emergency Guidelines

/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
For more DOT Emergency Guidelines (Complete) data for THIOPHENE (8 total), please visit the HSDB record page.

11.9.2 Shipping Name / Number DOT/UN/NA/IMO

UN 2414; Thiophene
IMO 3.2; Thiophene

11.9.3 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 15, 2006: https://www.ecfr.gov
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
International Air Transport Association. Dangerous Goods Regulations. 47th Edition. Montreal, Quebec Canada. 2006., p. 261
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
International Maritime Organization. International Maritime Dangerous Goods Code. London, UK. 2004., p. 114

11.9.4 DOT Label

Flammable Liquid

11.9.5 UN Classification

UN Hazard Class: 3; UN Pack Group: II

11.10 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Thiophene
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Thiophene: HSNO Approval: HSR001226 Approved with controls

12 Toxicity

12.1 Toxicological Information

12.1.1 EPA Provisional Peer-Reviewed Toxicity Values

Chemical Substance
PPRTV Assessment
Weight-Of-Evidence (WOE)
Inadequate information to assess carcinogenic potential
Last Revision
2007

12.1.2 Exposure Routes

The substance can be absorbed into the body by inhalation of its vapour.

12.1.3 Symptoms

Inhalation Exposure
Cough. Dizziness. Sore throat.
Skin Exposure
Redness.
Eye Exposure
Redness. Pain.

12.1.4 Adverse Effects

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Dermatotoxin - Skin burns.

12.1.5 Acute Effects

12.1.6 Toxicity Data

LC50 (mice) = 9,500 mg/m3/2H

12.1.7 Antidote and Emergency Treatment

For immediate first aid: Ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Sulfur and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 433
For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Anticipate seizures and treat if necessary ... Monitor for shock and treat if necessary ... For eye contamination, flush eye immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... Cover skin burns with sterile dressings after decontamination ... . /Sulfur and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 433

12.1.8 Human Toxicity Excerpts

In man, tiophene has caused skin irritation and may induce sensitization responses. Nausea, itching and jaundice were seen in a woman repeatedly taking thiophene in suppositories.
BIBRA Working Group; Toxicity Profile. The British Industrial Biological Research Association (1989)

12.1.9 Non-Human Toxicity Excerpts

INHALATION OF 3 OR 20 MG/CU M OF THIOPHENE BY RATS OVER 80 DAY PERIOD DECR ADRENAL, KIDNEY, LIVER, & BRAIN ASCORBIC ACID (VITAMIN C) LEVELS. ACCOMPANIED BY DEHYDROASCORBIC ACID & DIKETOGULONIC ACID ACCUMULATION IN LIVER & INCR URINARY EXCRETION OF 17-KETO STEROIDS.
PUSHKINA NN ET AL; GIG SANIT 32 (10): 103 (1967)
SELECTIVE NECROSIS OF GRANULAR LAYER OF CEREBELLUM WAS INDUCED IN 14 OR 25 RATS BY SC INJECTION OF THIOPHEN. PYKNOSIS OF GRANULAR CELL NUCLEI WAS SEEN BEFORE ANY ALTERATION IN ENZYMES IN CYTOPLASM.
ALBRECHTSEN R, JENSEN H; ACTA NEUROPATHOL 26(3) 217 (1973)
FOLLOWING ADMIN OF THIOPHENE (0.4 ML/DAY FOR 5 & 9 DAYS) TO RATS, NADH-TETRAZOLIUM REDUCTASE ACTIVITY IN PURKINJE CELLS WAS DECR BY 70% BUT THAT IN GLOMERULI REMAINED UNCHANGED.
ALBRECHTSEN R, JENSEN H; IRCS LIBR COMPEND 1(1) (1974)
ALBINO RATS GIVEN DAILY SC INJECTION OF 0.4 ML HAD LONGER MITOCHONDRIA AND DENSITY OF MITOCHONDRIA WAS REDUCED FROM NORMAL VALUE OF 140.4 TO 105.8 IN PURKINJE CELLS.
ALBRECHTSEN R ET AL; ACT PATHOL MICROBIOL SCAND SECT A PATHOL 82(6) 791 (1974)
For more Non-Human Toxicity Excerpts (Complete) data for THIOPHENE (6 total), please visit the HSDB record page.

12.1.10 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=110-02-1]

12.2 Ecological Information

12.2.1 Environmental Fate / Exposure Summary

Thiophene is a naturally occurring substance found in coal tar and petroleum. It is also produced industrially for use as an organic synthesis reagent and may be released to the environment through a variety of waste streams. Based on an experimental vapor pressure of 79.7 mm Hg at 25 °C, thiophene is expected to exist solely in the vapor phase in the ambient atmosphere. Vapor-phase thiophene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl and nitrate radicals. The experimental atmospheric half-life of thiophene with hydroxyl radicals is about 40 hours and the half-life with nitrate radicals is about 2.5 nighttime hours. Volatilization from moist soil surfaces is expected based on an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mol. Thiophene is expected to have moderate mobility in soils based upon an estimated Koc value of 230. Volatilization from dry soil surfaces is expected based upon the vapor pressure of this compound. Aerobic and anaerobic biodegradation are not important environmental fate processes for this compound. Using a standard BOD dilution technique and an activated sludge inoculum, a theoretical BOD of 0% was observed during a 2 week incubation period. No biodegradation was observed when thiophene was incubated in an anoxic aquifer slurry for a period of 3 months. In water, thiophene may adsorb to sediment or particulate matter based on its estimated Koc value. This compound is expected to volatilize from water surfaces given its estimated Henry's Law constant. Estimated half-lives for a model river and model lake are 3 and 89 hours, respectively. The potential for bioconcentration in aquatic organisms is low based on experimental BCF values in the range of 2-7 measured for carp. The general population may be exposed to thiophene through inhalation and dermal contact with this compound and ingestion of food products containing or contaminated with thiophene. (SRC)

12.2.2 Natural Pollution Sources

Naturally occurring source of thiophene is petroleum(1,2).
(1) Pratt JW; Ullmann's Encycl of Indust Chem 5th ed Deerfield, Fl: VCH Publ A26: 793-802 (1995)
(2) Lewis RJ; Hawley's Condensed Chemical Dictionary. 12th ed. NY,NY: Van Nostrand Reinhold Co., p. 1145 (1993)

12.2.3 Artificial Pollution Sources

Thiophenes's production and use as an organic synthesis reagent and solvent(1,2) may result in its release to the environment through various waste streams(SRC).
(1) Pratt JW; Ullmann's Encycl of Indust Chem 5th ed Deerfield, Fl: VCH Publ A26: 793-802 (1995)
(2) Lewis RJ; Hawley's Condensed Chemical Dictionary. 12th ed. NY,NY: Van Nostrand Reinhold Co., p. 1145 (1993)

12.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 230(SRC), determined from an experimental log Kow of 1.81(2) and a recommended regression-derived equation(3), indicates that thiophene is expected to have moderate mobility in soil(SRC). Volatilization of thiophene is expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC), determined from an experimental vapor pressure of 79.7 mm Hg at 25 °C(4) and water solubility of 3,020 mg/l at 25 °C(5). Volatilization from dry soil surfaces is expected based upon the vapor pressure of this compound(SRC).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Hansch C, Leo A; Exploring QSAR Fundamentals and Applications in Chemistry and Biology. Washington, DC: Amer Chem Soc (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 4-9 (1990)
(4) Boublik T et al; The Vapor Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapor Pressures of Some Pure Substances in the Normal and Low Temperature Region. Vol 17. Amsterdam, Netherlands: Elsevier Sci Publ (1984)
(5) Yalkowski SH, Dannenfelser RM; Aquasol Database of Aqueous Solubility. Ver 5. College of Pharmacy, University of Arizona - Tucson, AZ (1992)
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 230, determined from an experimental log Kow of 1.81(2) and a recommended regression-derived equation(3), indicates that thiophene may adsorb to suspended solids and sediment in water(SRC). Thiophene is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC),determined from an experimental vapor pressure of 79.7 mm Hg at 25 °C(4) and water solubility of 3,020 mg/l at 25 °C(5). Estimated half-lives for a model river and model lake are 3 and 89, hours respectively(6,SRC). According to a classification scheme(7), experimental BCF values in the range of 2-7 measured for carp(8), suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradation is not expected to be an important fate process for this compound(SRC). Using a standard BOD dilution technique and an activated sludge inoculum, a theoretical BOD of 0% was observed during a 2 week incubation period(8). No biodegradation was observed when thiophene was incubated in an aquifer slurry for a period of 1 year(9).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Hansch C, Leo A; Exploring QSAR Fundamentals and Applications in Chemistry and Biology. Washington, DC: Amer Chem Soc (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 4-9, 5-4, 5-10, 15-1 to 15-29 (1990)
(4) Boublik et al; The Vapor Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapor Pressures of Some Pure Substances in the Normal and Low Temperature Region. Vol 17. Amsterdam, Netherlands: Elsevier Sci Publ (1984).
(5) Yalkowski SH, Dannenfelser RM; Aquasol Database of Aqueous Solubility. Ver 5. College of Pharmacy, University of Arizona - Tucson, AZ (1992)
(6) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(7) Franke C et al; Chemosphere 29: 1501-14 (1994)
(8) Chemicals Inspection and Testing Institute. Japan Chemical Industry Ecology - Toxicology and Information Center. ISBN 4-89074-101-1 (1992)
(9) Adrian NR, Suflita JM; Environ Toxicol Chem 13: 1551-1557 (1994)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiophene, which has an experimental vapor pressure of 79.7 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase thiophene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and nitrate radicals with experimental atmospheric half-life of about 40 hours and 2.5 nighttime hours, respectively(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Boublik T et al; The Vapor Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapor Pressures of Some Pure Substances in the Normal and Low Temperature Region. Vol 17. Amsterdam, Netherlands: Elsevier Sci Publ (1984)

12.2.5 Environmental Biodegradation

Biodegradation is not expected to be an important environmental fate process for thiophene(SRC). No biodegradation was observed when thiophene was incubated in an anoxic aquifer slurry for a period of 3 months(1). Using a standard BOD dilution technique and an activated sludge inoculum, a theoretical BOD of 0% was observed during a 2 week incubation period(2). No biodegradation was observed when thiophene was incubated in an aquifer slurry for a period of 1 year(3).
(1) Kuhn EP, Suflita JM; Environ Toxicol Chem 8: 1149-58 (1989)
(2) Chemicals Inspection and Testing Institute. Japan Chemical Industry Ecology - Toxicology and Information Center. ISBN 4-89074-101-1 (1992)
(3) Adrian NR, Suflita JM; Environ Toxicol Chem 13: 1551-1557 (1994)

12.2.6 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of thiophene with photochemically-produced hydroxyl radicals has been measured as 9.5X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 40 hours at an atmospheric concentration of 5.0X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the vapor-phase reaction of thiophene with photochemically-produced nitrate radicals has been measured as 3.9X10-14 cu cm/molecule-sec at 25 °C(2). This corresponds to an atmospheric half-life of about 2.5 nighttime hours at an atmospheric concentration of 2.0X10+9 nitrate radicals per cu cm(2,SRC). Thiophene is not expected to undergo hydrolysis or direct photolysis in the environment due to the lack of functional groups to hydrolyze or absorb UV radiation at environmentally significant wavelengths(SRC).
(1) Atkinson R; J Phys Chem Ref Data. Monograph No. 1 (1989)
(2) Sabljic A, Gusten H; Atmos Environ 24: 73-78 (1990)

12.2.7 Environmental Bioconcentration

Experimental BCF values in the range of 2-7 were measured for carp(1). According to a classification scheme(2), these BCF values suggest that bioconcentration in aquatic organisms is low(SRC).
(1) Chemicals Inspection and Testing Institute. Japan Chemical Industry Ecology - Toxicology and Information Center. ISBN 4-89074-101-1 (1992)
(2) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.8 Soil Adsorption / Mobility

The Koc of thiophene is estimated as approximately 230(SRC), using a measured log Kow of 1.81(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that thiophene is expected to have moderate mobility in soil(SRC).
(1) Hansch C et al; Exploring QSAR Hydrophobic, Electronic and Stearic Constants Washington DC: Amer Chem Soc (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 23 (1983)

12.2.9 Volatilization from Water / Soil

The Henry's Law constant for thiophene is estimated as 2.9X10-3 atm-cu m/mole(SRC) from its experimental value for vapor pressure, 79.7 mm Hg(1), and experimental water solubility, 3,020 mg/l(2). This value indicates that thiophene will volatilize from water surfaces(3,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 3 hours(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 89 hours(3,SRC). Thiophene's Henry's Law constant(SRC) and vapor pressure indicates that volatilization from moist and dry soil surfaces is important(SRC).
(1) Boublik et al; The Vapor Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapor Pressures of Some Pure Substances in the Normal and Low Temperature Region. Vol 17. Amsterdam, Netherlands: Elsevier Sci Publ (1984)
(2) Yalkowsky SH, Dannenfelser RM; Aquasol Database of Aqueous Solubility Ver 5. Univ Ariz Tucson AR (1992)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

12.2.10 Environmental Water Concentrations

SURFACE WATER: Trace concentrations of thiophene were detected, not quantified in Antarctic lakes and waterways(1).
(1) Roberts NJ, Burton HR; Chemosphere 29: 1627-37 (1994)

12.2.11 Effluent Concentrations

Thiophene was detected, not quantified, in the gas emissions of a Norwegian waste incinerator(1). Thiophene was detected at concentrations of 20-620 ppb in the leachate of a shale oil processing facility(2). Thiophene was detected in air samples above wastewater from shale oil processing facilities in Colorado and Utah at concentrations of 1-10 ng/l(3).
(1) Benestad C et al; Chemosphere 16: 813-20 (1987)
(2) Pellizari ED et al; ASTM Spec Tech Publ. STP 686: 256-74 (1979)
(3) Hawthorne SB, Sievers RE; Environ Sci Technol 18: 483-90 (1984)

12.2.12 Food Survey Values

Thiophene was detected in the volatiles of Idaho Russet baked potatoes(1) and meat volatiles(2).
(1) Coleman EC et al; J Agric Food Chem 29: 42-48 (1981)
(2) Shahidi et al; CRC Crit Rev Food Sci Nature 24: 141-243 (1986)

12.2.13 Probable Routes of Human Exposure

Occupational exposure to thiophene may occur through inhalation or dermal contact at facilities where this compound is produced(1). The general population will be exposed to thiophene through the ingestion of contaminated food or water(SRC).
(1) Pratt JW; Ullmann's Encycl of Indust Chem 5th ed Deerfield, Fl: VCH Publ A26: 793-802 (1995)

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Chemical-Target Interactions

16.2 Pathways

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

19 Classification

19.1 MeSH Tree

19.2 ChEBI Ontology

19.3 ChemIDplus

19.4 CAMEO Chemicals

19.5 ChEMBL Target Tree

19.6 UN GHS Classification

19.7 EPA CPDat Classification

19.8 NORMAN Suspect List Exchange Classification

19.9 EPA DSSTox Classification

19.10 EPA TSCA and CDR Classification

19.11 LOTUS Tree

19.12 EPA Substance Registry Services Tree

19.13 MolGenie Organic Chemistry Ontology

20 Information Sources

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  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
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  9. EPA Provisional Peer-Reviewed Toxicity Values (PPRTVs)
  10. European Chemicals Agency (ECHA)
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  12. Hazardous Substances Data Bank (HSDB)
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  15. NJDOH RTK Hazardous Substance List
  16. Risk Assessment Information System (RAIS)
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  19. ChEBI
  20. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  21. Yeast Metabolome Database (YMDB)
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  22. ChEMBL
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  25. EPA Chemical and Products Database (CPDat)
  26. NITE-CMC
    Thiophene - FY2009 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/09-mhlw-0069e.html
  27. NMRShiftDB
  28. SpectraBase
  29. Japan Chemical Substance Dictionary (Nikkaji)
  30. KNApSAcK Species-Metabolite Database
  31. Natural Product Activity and Species Source (NPASS)
  32. MarkerDB
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  33. Metabolomics Workbench
  34. NIST Mass Spectrometry Data Center
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  35. Springer Nature
  36. SpringerMaterials
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  43. GHS Classification (UNECE)
  44. NORMAN Suspect List Exchange
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  45. EPA Substance Registry Services
  46. MolGenie
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  47. PATENTSCOPE (WIPO)
CONTENTS