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2,4,6-Trinitrobenzoic acid

PubChem CID
8518
Structure
2,4,6-Trinitrobenzoic acid_small.png
2,4,6-Trinitrobenzoic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 2,4,6-TRINITROBENZOIC ACID
  • 129-66-8
  • Trinitrobenzoic acid
  • s-Trinitrobenzoic acid
  • Benzoic acid, 2,4,6-trinitro-
Molecular Weight
257.11 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-27
Description
Trinitrobenzoic acid appears as a yellow crystalline solid high explosive. Easily ignited and burns vigorously when dry. Insoluble in water. Will burn when wet, although may be difficult to ignite. Produces toxic oxides of nitrogen during combustion. May explode under exposure to heat or fire. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments.
Trinitrobenzoic acid, wetted with not less than 30% water appears as a sludge of yellow crystals. The dry material is a high explosive, is easily ignited and burns very vigorously. The wet material can burn but may require some effort to ignite. Insoluble in water. Produces toxic oxides of nitrogen during combustion.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2,4,6-Trinitrobenzoic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,4,6-trinitrobenzoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C7H3N3O8/c11-7(12)6-4(9(15)16)1-3(8(13)14)2-5(6)10(17)18/h1-2H,(H,11,12)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

KAQBNBSMMVTKRN-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1=C(C=C(C(=C1[N+](=O)[O-])C(=O)O)[N+](=O)[O-])[N+](=O)[O-]
Computed by OEChem 2.3.0 (PubChem release 2024.11.20)

2.2 Molecular Formula

C7H3N3O8
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

129-66-8

35860-50-5

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 UN Number

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 NSC Number

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
257.11 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
0.2
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
256.99201406 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
256.99201406 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
175Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
18
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
369
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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

Trinitrobenzoic acid appears as a yellow crystalline solid high explosive. Easily ignited and burns vigorously when dry. Insoluble in water. Will burn when wet, although may be difficult to ignite. Produces toxic oxides of nitrogen during combustion. May explode under exposure to heat or fire. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments.
Trinitrobenzoic acid, wetted with not less than 30% water appears as a sludge of yellow crystals. The dry material is a high explosive, is easily ignited and burns very vigorously. The wet material can burn but may require some effort to ignite. Insoluble in water. Produces toxic oxides of nitrogen during combustion.
Solid; [Merck Index] Off-white crystalline solid; [Chem Service MSDS]

3.2.2 Color / Form

Orthorhombic or rhombohedral crystals from water
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3602

3.2.3 Melting Point

228.7 °C (decomposes)
Lide, D.R. CRC Handbook of Chemistry and Physics 88TH Edition 2007-2008. CRC Press, Taylor & Francis, Boca Raton, FL 2007, p. 3-510
White needles from water crystallizing with 2 molecules of water; MP: 160 °C with decomposition, at 55 °C gives up 2 water molecules; soluble in alcohol /2,3,6-Trinitrobenzoic acid/
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 64th ed. Boca Raton, Florida: CRC Press Inc., 1983-84., p. C-159
Yellow needles from ether crystallizing with 1 molecule of ether; MP: 168 °C with decomposition; soluble in ether /3,4,5-Trinitrobenzoic acid/
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 64th ed. Boca Raton, Florida: CRC Press Inc., 1983-84., p. C-159
Yellow leaves or plates from water; MP: 194.5 °C with decomposition; soluble in alcohol, ether, benzene, water /2,4,5-Trinitrobenzoic acid/
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 64th ed. Boca Raton, Florida: CRC Press Inc., 1983-84., p. C-159

3.2.4 Solubility

Soluble in acetone, methanol; slightly soluble in benzene; at 25 °C: 26.6% in alcohol, 14.7% in ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1671
In water, 2.012X10+4 mg/L at 23.5 °C
Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 342

3.2.5 Vapor Pressure

0.00000001 [mmHg]

3.2.6 Decomposition

Sublimes with decomposition forming CO2 and trinitrobenzene.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1671
When heated to decomposition it emits toxic fumes of /nitroxides./
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3602

3.2.7 Dissociation Constants

pKa = 0.65 at 25 °C
Kortum G et al; Dissociation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry. London: Butterworth (1961)

3.2.8 Other Experimental Properties

Sublimes with decomposition forming carbon dioxide and trinitrobenzene
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1671
Dangerous, explodes by heat or shock
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 1284
When heated to decomposition it emits toxic fumes of NOx.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3602

3.3 Chemical Classes

Nitrogen Compounds -> Nitrobenzoic Acids

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Instrument Name
Bruker WH-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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2 of 2
Instrument Name
Jeol FX-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.1.3 15N NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
NIST Number
253388
Library
Main library
Total Peaks
35
m/z Top Peak
74
m/z 2nd Highest
75
m/z 3rd Highest
44
Thumbnail
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2 of 2
Source of Spectrum
KO-11-598-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3 UV Spectra

MAX ABSORPTION (DIETHYLAMINE): 475 NM (LOG E= 2.90)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-200
UV: 331 (Sadtler Research Laboratories Spectral Collection)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 1523

4.4 IR Spectra

IR Spectra
IR: 217 (Sadtler Research Laboratories IR Grating Collection)

4.4.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
THE EDWAL LABORATORIES, INC., RINGWOOD, ILLINOIS
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Other Spectra

SADTLER REFERENCE NUMBER: 1112 (IR, PRISM)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-200

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

The disposition and metabolism of 2,4,6-trinitrotoluene (TNT) was studied in rats, mice, rabbits, and dogs following oral, dermal or intratracheal admin of single doses of 14(C)-ring labeled compound. TNT was extensively metabolized in all species. Trinitrobenzoic acid was detected occasionally.
Elhawari AM et al; Species differences in the disposition and metabolism of 2,4,6-trinitrotoluene as a function of route of administration; Govt Reports Announcements & Index (GRA&I), (17): (1982)

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used as a pH indicator, intermediate for CI developer 19 (phloroglucinol), and in explosive compositions; [HSDB]
Used as an indicator for pH ranges between 12.0-13.4
Sabnis RW et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (2008). New York, NY: John Wiley & Sons; Indicator Reagents. Online Posting Date: April 15, 2009.
Explosive compositions
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 1284
CHEM INT FOR CI DEVELOPER 19 (PHLOROGLUCINOL)
SRI

8.1.1 Use Classification

Hazard Classes and Categories -> Flammable - 4th degree, Reactive - 4th degree

8.2 Methods of Manufacturing

Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 1284

8.3 Formulations / Preparations

TRINITROBENZOIC ACID, WET, CONTAINING @ LEAST 10% WATER; TRINITROBENZOIC ACID, WET, CONTAINING LESS THAN 30% WATER.
U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 85/8312

8.4 U.S. Production

(1972) PROBABLY LESS THAN 4.54X10+5 G
SRI
(1975) PROBABLY LESS THAN 4.54X10+5 G
SRI

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Explosive
Signal
Danger
GHS Hazard Statements
H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]
Precautionary Statement Codes

P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, and P501

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

9.1.2 Hazard Classes and Categories

Explosives - Division 1.1
Flammable - 4th degree, Reactive - 4th degree

9.1.3 Health Hazards

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Fire may produce irritating, corrosive and/or toxic gases. (ERG, 2024)

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

ERG 2024, Guide 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

· Contact may cause burns to skin and eyes.

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

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

9.1.4 Fire Hazards

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

MAY EXPLODE AND THROW FRAGMENTS 1600 METERS (1 MILE) OR MORE IF FIRE REACHES CARGO. (ERG, 2024)

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Flammable/combustible material. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; treat as an explosive (ERG Guide 112). Keep material wet with water or treat as an explosive (ERG Guide 112). Runoff to sewer may create fire or explosion hazard. (ERG, 2024)

ERG 2024, Guide 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

· Flammable/combustible material.

· May be ignited by heat, sparks or flames.

· DRIED OUT material may explode if exposed to heat, flame, friction or shock; treat as an explosive (GUIDE 112).

· Keep material wet with water or treat as an explosive (GUIDE 112).

· Runoff to sewer may create fire or explosion hazard.

9.1.5 Hazards Summary

Explodes by heat or shock; [Hawley] May cause burns to skin and eyes; [CAMEO] An irritant; May cause blood disorders and injury to liver, kidney, and nervous system; [Chem Service MSDS] See 2,4,6-Trinitrotoluene.
Hawley - Lewis RJ. _Hawley's Condensed Chemical Dictionary, _15th Ed. New York: John Wiley & Sons, 2007.

9.1.6 Fire Potential

Dry, the material is easily ignited and will burn vigorously. The wet material can burn though it may require some effort to ignite.
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918

9.1.7 EPA Hazardous Waste Number

D003; A waste containing 2,4,6-trinitrobenzoic acid may (or may not) be characterized a hazardous waste following testing for the reactivity characteristics as prescribed by the Resource Conservation and Recovery Act (RCRA) regulations.

9.2 Safety and Hazard Properties

9.2.1 Explosive Limits and Potential

The dry material is a high explosive.
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
Explodes by heat or shock.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 1284

9.3 First Aid Measures

9.3.1 First Aid

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Refer to the "General First Aid" section. (ERG, 2024)

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Refer to the "General First Aid" section. (ERG, 2024)

ERG 2024, Guide 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

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.

In Canada, an Emergency Response Assistance Plan (ERAP) may be required for this product. Please consult the shipping paper and/or the "ERAP" section.

9.4 Fire Fighting

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

CARGO FIRE: DO NOT fight fire when fire reaches cargo! Cargo may EXPLODE! Stop all traffic and clear the area for at least 1600 meters (1 mile) in all directions and let burn. Do not move cargo or vehicle if cargo has been exposed to heat.

TIRE OR VEHICLE FIRE: Use plenty of water - FLOOD it! If water is not available, use CO2, dry chemical or dirt. If possible, and WITHOUT RISK, use unmanned master stream devices or monitor nozzles from maximum distance to prevent fire from spreading to cargo area. Pay special attention to tire fires as re-ignition may occur. Stand by, at a safe distance, with extinguisher ready for possible re-ignition. (ERG, 2024)

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

CARGO FIRE: DO NOT fight fire when fire reaches cargo! Cargo may EXPLODE! Stop all traffic and clear the area for at least 1600 meters (1 mile) in all directions and let burn. Do not move cargo or vehicle if cargo has been exposed to heat.

TIRE OR VEHICLE FIRE: Use plenty of water - FLOOD it! If water is not available, use CO2, dry chemical or dirt. If possible, and WITHOUT RISK, use unmanned master stream devices or monitor nozzles from maximum distance to prevent fire from spreading to cargo area. Pay special attention to tire fires as re-ignition may occur. Stand by, at a safe distance, with extinguisher ready for possible re-ignition. (ERG, 2024)

9.4.1 Fire Fighting Procedures

If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. /Trinitrobenzoic acid, dry/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
Evacuation: If fire becomes uncontrollable, consider evacuation of one (1) mile radius. /Trinitrobenzoic acid, dry/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
If material on fire or involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Cover all suspected material with wet sand or earth to prevent ignition until material can be permanently disposed of. /Trinitrobenzoic acid, wetted with not less than 10% water by mass/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
If material on fire or involved in fire: Dangerously explosive. Flood with water. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Trinitrobenzoic acid, wetted with not less than 30% water by mass/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
For more Fire Fighting Procedures (Complete) data for 2,4,6-Trinitrobenzoic acid (6 total), please visit the HSDB record page.

9.4.2 Firefighting Hazards

The primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments. /Trinitrobenzoic acid, dry/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918

9.5 Accidental Release Measures

Public Safety: ERG 2024, Guide 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

· 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 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

· 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.

Small Spill

· Flush area with large amounts of water.

Large Spill

· Wet down with water and dike for later disposal.

· KEEP "WETTED" PRODUCT WET BY SLOWLY ADDING FLOODING QUANTITIES OF WATER.

9.5.1 Isolation and Evacuation

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area immediately for at least 500 meters (1/3 mile) in all directions.

LARGE SPILL: Consider initial evacuation for 800 meters (1/2 mile) in all directions.

FIRE: If rail car or trailer is involved in a fire, ISOLATE for 1600 meters (1 mile) in all directions; also, initiate evacuation including emergency responders for 1600 meters (1 mile) in all directions. (ERG, 2024)

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area immediately for at least 100 meters (330 feet) in all directions.

LARGE SPILL: Consider initial evacuation for 500 meters (1/3 mile) in all directions.

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 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

Immediate precautionary measure

· Isolate spill or leak area immediately for at least 100 meters (330 feet) in all directions.

Large Spill

· Consider initial evacuation for 500 meters (1/3 mile) in all directions.

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.

9.5.2 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

9.5.3 Preventive Measures

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep spilled material wet. Wet spilled material bfore picking it up. Do not attempt to sweep up dry material. /Trinitrobenzoic acid, dry/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Cover all suspected material with wet sand or earth to prevent ignition until material can be permanently disposed of. /Trinitrobenzoic acid, wetted with not less than 10% water by mass/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
Personnel protection: Avoid breathing dusts, and fumes from burning material ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Trinitrobenzoic acid, dry; trinitrobenzoic acid, wetted with not less than 10% water by mass/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Keep spilled material wet. Do not attempt to sweep up dry material. /Trinitrobenzoic acid, wetted with not less than 30% water by mass/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918
Personnel protection: Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Trinitrobenzoic acid, wetted with not less than 30% water by mass/
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918

9.6 Handling and Storage

9.6.1 Nonfire Spill Response

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

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. DO NOT OPERATE RADIO TRANSMITTERS WITHIN 100 METERS (330 FEET) OF ELECTRIC DETONATORS. DO NOT CLEAN-UP OR DISPOSE OF, EXCEPT UNDER SUPERVISION OF A SPECIALIST. (ERG, 2024)

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

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.

SMALL SPILL: Flush area with large amounts of water.

LARGE SPILL: Wet down with water and dike for later disposal. KEEP "WETTED" PRODUCT WET BY SLOWLY ADDING FLOODING QUANTITIES OF WATER. (ERG, 2024)

9.7 Exposure Control and Personal Protection

Protective Clothing: ERG 2024, Guide 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

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

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

9.7.1 Emergency Response Planning Guidelines

Emergency Response: ERG 2024, Guide 113 (Trinitrobenzoic acid, wetted with not less than 30% water; Trinitrobenzoic acid, wetted with not less than 10% water)

CARGO Fire

· DO NOT fight fire when fire reaches cargo! Cargo may EXPLODE!

· Stop all traffic and clear the area for at least 1600 meters (1 mile) in all directions and let burn.

· Do not move cargo or vehicle if cargo has been exposed to heat.

TIRE or VEHICLE Fire

· Use plenty of water - FLOOD it! If water is not available, use CO2, dry chemical or dirt.

· If possible, and WITHOUT RISK, use unmanned master stream devices or monitor nozzles from maximum distance to prevent fire from spreading to cargo area.

· Pay special attention to tire fires as re-ignition may occur. Stand by, at a safe distance, with extinguisher ready for possible re-ignition.

9.7.2 Personal Protective Equipment (PPE)

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

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

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

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

Wear appropriate chemical protective gloves and goggles.
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918

9.8 Stability and Reactivity

9.8.1 Air and Water Reactions

Highly flammable. Insoluble in water.

9.8.2 Reactive Group

Acids, Strong Oxidizing

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Acids, Carboxylic

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Water and Aqueous Solutions

9.8.3 Reactivity Alerts

Highly Flammable

Explosive

Strong Oxidizing Agent

Highly Flammable

Strong Oxidizing Agent

9.8.4 Reactivity Profile

Aromatic nitro compounds, such as TRINITROBENZOIC ACID, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. All heavy metal salts of this compound are explosive on heating or impact.
Aromatic nitro compounds, such as TRINITROBENZOIC ACID, WETTED WITH NOT LESS THAN 30% WATER, are oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; Treat as an explosive. All heavy metal salts of this compound are explosive on heating or impact.

9.8.5 Hazardous Reactivities and Incompatibilities

Reacts with heavy metals to form heat- or impact-sensitive explosive salts.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3602
During oxidation of TNT /trinitrotoluene/ in sulfuric acid to trinitrobenzoic acid, stirring of the viscous reaction mixture must be very effective to prevent added portions of solid dichromate causing local ignition.
Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 1078

9.9 Transport Information

9.9.1 DOT Emergency Guidelines

/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Fire or Explosion: Flammable/combustible material. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; treat as an explosive (GUIDE 112). Keep material wet with water or treat as an explosive (Guide 112). Runoff to sewer may create fire or explosion hazard. /Trinitrobenzoic acid, wetted with not less than 10% water; Trinitrobenzoic acid, wetted with not less than 30% water/
U.S. Department of Transportation. 2008 Emergency Response Guidebook. Washington, D.C. 2008
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Health: Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution. /Trinitrobenzoic acid, wetted with not less than 10% water; Trinitrobenzoic acid, wetted with not less than 30% water/
U.S. Department of Transportation. 2008 Emergency Response Guidebook. Washington, D.C. 2008
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Public Safety: CALL Emergency Response Telephone Number. ... Isolate spill or leak area immediately for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Ventilate closed spaces before entering. /Trinitrobenzoic acid, wetted with not less than 10% water; Trinitrobenzoic acid, wetted with not less than 30% water/
U.S. Department of Transportation. 2008 Emergency Response Guidebook. Washington, D.C. 2008
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Trinitrobenzoic acid, wetted with not less than 10% water; Trinitrobenzoic acid, wetted with not less than 30% water/
U.S. Department of Transportation. 2008 Emergency Response Guidebook. Washington, D.C. 2008
For more DOT Emergency Guidelines (Complete) data for 2,4,6-Trinitrobenzoic acid (8 total), please visit the HSDB record page.

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

IMO 4.1; Trinitrobenzoic acid, wetted with 30% or more water, by weight
UN 0215; Trinitrobenzoic acid, dry or wetted with less than 30% water, by weight
IMO 1.1; Trinitrobenzoic acid, dry or wetted with less than 30% water, by weight

9.9.3 Standard Transportation Number

49 015 70; Trinitrobenzoic acid, dry (high explosive)
49 171 50; Trinitrobenzoic acid, wet (containing at least 10% water)
49 015 71; Trinitrobenzoic acid, wet, containing at least 10% water over 16 ounces in one outside package

9.9.4 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 (7/1/96)
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.
IATA. Dangerous Goods Regulations. 38th ed. Montreal, Canada and Geneva, Switzerland: International Air Transport Association, Dangerous Goods Board, January, 1997., p. 226
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.
IMDG; International Maritime Dangerous Goods Code; International Maritime Organization p.1132, 4066, 4066-1 (1988)

9.9.5 DOT Label

Explosive 1.1D
Flammable Solid

9.10 Regulatory Information

9.10.1 DHS Chemicals of Interest (COI)

Chemicals of Interest(COI)
Trinitrobenzoic acid
Release: Minimum Concentration (%)
A Commercial Grade
Release: Screening Threshold Quantities (in pounds)
5000
Theft: Minimum Concentration (%)
A Commercial Grade
Theft: Screening Threshold Quantities (in pounds unless otherwise noted)
400
Security Issue: Release - Explosives
Explosive chemical that can be released at a facility.
Security Issue: Theft - EXP/IEDP
Explosive/Improvised Explosive Device Precursor material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.

9.10.2 RCRA Requirements

D003; A solid waste containing 2,4,6-trinitrobenzoic acid may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
40 CFR 261.23; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of December 6, 2010: https://www.ecfr.gov

9.11 Other Safety Information

9.11.1 Toxic Combustion Products

Toxic oxides of nitrogen are produced during combustion of this material.
Association of American Railroads; Bureau of Explosives. Emergency Handling of Hazardous Materials in Surface Transportation. Association of American Railroads, Pueblo, CO. 2005, p. 918

10 Toxicity

10.1 Toxicological Information

10.1.1 Adverse Effects

Dermatotoxin - Skin burns.

10.1.2 Antidote and Emergency Treatment

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as 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 patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 176
Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 176-7
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 177

10.1.3 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Intraperitoneal administration of meta-nitrobenzoic, 3,5-dinitrobenzoic, 2,4,6-trinitrobenzoic and 3,5-dinitro-4-methylbenzoic acids to white mice in a dose equal to the LD50 induced an increase in the methemoglobin content in their blood. Total activity of dehydrogenases of the pentophosphate path, content of 2,3-diphosphoglycerate increase in response to the intoxication evoked by the mentioned acids. The acute intoxication does not practically change the activity of the key enzymes of antioxidant protection: superoxide-dismutase, catalase and glutathione peroxidase.
Shugalei IV et al; Ukr Biokhim ZH 64 (4): 98-101 (1992)
/ALTERNATIVE and IN VITRO TESTS/ 2,4,6-Trinitrobenzoic acid accelerated the release of acetylcholine from the nerve endings and induced contractions in isolated small intestine from guinea pigs.
TAKAGI K, TAKAYANAGI I; ARCH INT PHARMACODYN THER 155 (2): 373-80 (1965)

10.2 Ecological Information

10.2.1 Ecotoxicity Excerpts

/AQUATIC SPECIES/ Aqueous samples containing various explosives, their reduced metabolites, as well as related compounds were subjected to the luminescent bacterium Vibrio fischeri NRRLB-11177 to determine ... the EC50 values of 24 test compounds ... /2,4,6-trinitrobenzoic acid/ (TNBA)must be classified in the category "very toxic to aquatic organisms."
Drzyzga O et al; Arch Environ Contam Toxicol 28 (2): 229-35 (1995)

10.2.2 Environmental Fate / Exposure Summary

2,4,6-Trinitrobenzoic acid's production and use as a pH indicator and in explosive compositions may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 7.23X10-9 mm Hg at 25 °C indicates 2,4,6-trinitrobenzoic acid will exist solely in the particulate phase in the atmosphere. Particulate-phase 2,4,6-trinitrobenzoic acid will be removed from the atmosphere by wet or dry deposition. 2,4,6-Trinitrobenzoic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, 2,4,6-trinitrobenzoic acid is expected to have moderate mobility based upon an estimated Koc of 200. However, the pKa of 2,4,6-trinitrobenzoic acid is 0.65, indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.62X10-14 atm-cu m/mole. After 180 minutes, very little oxygen consumption by phenol-adapted biological cultures occurred with 2,4,6-trinitrobenzoic acid, suggesting that biodegradation is not an important environmental fate process. If released into water, 2,4,6-trinitrobenzoic acid is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant and its pKa. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 2,4,6-trinitrobenzoic acid may occur through inhalation of mists and dermal contact with this compound at workplaces where 2,4,6-trinitrobenzoic acid is produced or used. (SRC)

10.2.3 Artificial Pollution Sources

2,4,6-Trinitrobenzoic acid's production and use as a pH indicator(1) and in explosive compositions(2) may result in its release to the environment through various waste streams(SRC).
(1) Sabnis RW et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (2008). New York, NY: John Wiley & Sons; Indicator Reagents. Online Posting Date: April 15, 2009
(2) Lewis RJ; Hawley's Condensed Chem Dict, 15th ed., New York, NY: John Wiley & Sons, Inc. p. 1284 (2007)

10.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a structure estimation method(2), indicates that 2,4,6-trinitrobenzoic acid is expected to have moderate mobility in soil(SRC). However, the pKa of 2,4,6-trinitrobenzoic acid is 0.65(3), indicating that this compound will almost entirely exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of 2,4,6-trinitrobenzoic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.62X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2,4,6-Trinitrobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.23X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(6). After 180 minutes, very little oxygen consumption by phenol-adapted biological cultures occurred with 2,4,6-trinitrobenzoic acid(7), suggesting that biodegradation is not an important environmental fate process in soil(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of April 22, 2010: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Kortum G et al; Dissociation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry. London: Butterworth (1961)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(5) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(6) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(7) Chambers CW et al; J Water Pollut Contr Fed 35: 1517-28 (1963)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a structure estimation method(2), indicates that 2,4,6-trinitrobenzoic acid is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.62X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A pKa of 0.65(5) indicates 2,4,6-trinitrobenzoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(6). According to a classification scheme(7), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.23(8) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). After 180 minutes, very little oxygen consumption by phenol-adapted biological cultures occurred with 2,4,6-trinitrobenzoic acid(9), suggesting that biodegradation is not an important environmental fate process in water(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of April 22, 2010: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Kortum G et al; Dissociation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry. London: Butterworth (1961)
(6) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(7) Franke C et al; Chemosphere 29: 1501-14 (1994)
(8) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(9) Chambers CW et al; J Water Pollut Contr Fed 35: 1517-28 (1963)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,6-trinitrobenzoic acid, which has an estimated vapor pressure of 7.23X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 2,4,6-trinitrobenzoic acid may be removed from the air by wet or dry deposition(SRC). 2,4,6-Trinitrobenzoic acid does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

10.2.5 Environmental Biodegradation

AEROBIC: After 180 minutes, very little oxygen consumption by phenol adapted biological cultures occurred with 2,4,6-trinitrobenzoic acid(1). The amounts of oxygen consumed after the 180 minute test time are 53 uL (endogenous), 61 uL (cells plus 100 mg/L 2,4,6-trinitrobenzoic acid), and 342 uL (cells plus phenol, after 90 minutes) which results in a ratio of only 1.2 endogenous to 2,4,6-trinitrobenzoic acid oxygen consumption(1). The trinitro derivatives of benzoic acid were more readily reduced in the presence of enzyme preparations from Veillonella alkalescens than the toluene or phenol derivatives and are degraded more slowly than the mononitro and dinitro derivatives of benzoic acid, toluene, or phenol(2). Three moles of hydrogen are required to reduce each nitro group to the amino group(2). These data suggest that biodegradation is not expected to be an important fate process in the environment(SRC).
(1) Chambers CW et al; J Water Pollut Contr Fed 35: 1517-28 (1963)
(2) McCormick NG et al; Appl Environ Microbiol 31: 949-58 (1976)

10.2.6 Environmental Abiotic Degradation

2,4,6-Trinitrobenzoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). 2,4,6-Trinitrobenzoic acid does not contain chromophores that absorb at wavelengths >290 nm(1) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

10.2.7 Environmental Bioconcentration

An estimated BCF of 3.2 was calculated in fish for 2,4,6-trinitrobenzoic acid(SRC), using an estimated log Kow of 0.23(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of April 22, 2010: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

10.2.8 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,4,6-trinitrobenzoic acid can be estimated to be 200(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,4,6-trinitrobenzoic acid is expected to have moderate mobility in soil. However, the pKa of 2,4,6-trinitrobenzoic acid is 0.65(3), indicating that this compound will almost entirely exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.0. Jan, 2009. Available from, as of April 22, 2010: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) Kortum G et al; Dissociation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry. London: Butterworth (1961)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

10.2.9 Volatilization from Water / Soil

The Henry's Law constant for 2,4,6-trinitrobenzoic acid is estimated as 2.62X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4,6-trinitrobenzoic acid is expected to be essentially nonvolatile from water surfaces(2). 2,4,6-Trinitrobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.23X10-9 mm Hg(SRC), determined from a fragment constant method(3).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)

10.2.10 Effluent Concentrations

2,4,6-Trinitrobenzoic acid was detected at 0.80 mg/L (0.34% of total sample) in raw trinitrotoluene wastes (pH of 2) from a counter-current, continuous flow trinitrotoluene manufacturing process(1). 2,4,6-Trinitrobenzoic acid was detected, not quantified, in the leachate water of a disposal site of a former ammunition plant in Stadtallendor, Germany, sampling date not reported(2).
(1) Nay MW JR et al; Industrial Wastes 18: 20-9 (1972)
(2) Schmidt TC et al; Chemosphere 37: 1079-90 (1998)

10.2.11 Probable Routes of Human Exposure

Occupational exposure to 2,4,6-trinitrobenzoic acid may occur through inhalation and dermal contact with this compound at workplaces where 2,4,6-trinitrobenzoic acid is produced or used(SRC). Mist from hot charges, leaking lines, steaming operations, and hot drainage ditches are sources of skin exposure and contamination of the work environment in the production of aromatic nitro compounds(1).
(1) Parmeggiani L; Encycl Occup Health & Safety 3rd ed Geneva, Switzerland: International Labour Office pg 1451-3 (1983)

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

11.3 Chemical Co-Occurrences in Literature

11.4 Chemical-Gene Co-Occurrences in Literature

11.5 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 ChemIDplus

14.2 CAMEO Chemicals

14.3 UN GHS Classification

14.4 NORMAN Suspect List Exchange Classification

14.5 EPA DSSTox Classification

14.6 EPA Substance Registry Services Tree

14.7 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    TRINITROBENZOIC ACID, WETTED WITH NOT LESS THAN 30% WATER
    https://cameochemicals.noaa.gov/chemical/4725
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DHS Chemical Facility Anti-Terrorism Standards (CFATS) Chemicals of Interest
  5. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  8. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. Hazardous Substances Data Bank (HSDB)
  10. NJDOH RTK Hazardous Substance List
  11. Emergency Response Guidebook (ERG)
  12. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
    2,4,6-Trinitrobenzoic acid
    https://haz-map.com/Agents/3445
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Benzoic acid, 2,4,6-trinitro-
    http://www.nist.gov/srd/nist1a.cfm
  15. SpectraBase
    1-CARBOXY-2,4,6-TRINITROBENZENE
    https://spectrabase.com/spectrum/5QlaQvARBfT
  16. NITE-CMC
    Trinitrobenzoic acid - FY2007 (Dangerous substance)
    https://www.chem-info.nite.go.jp/chem/english/ghs/07-mhlw-0015e.html
  17. NMRShiftDB
  18. Springer Nature
  19. Wikidata
    2,4,6-trinitrobenzoic acid
    https://www.wikidata.org/wiki/Q209194
  20. Wikipedia
  21. PubChem
  22. GHS Classification (UNECE)
  23. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  24. EPA Substance Registry Services
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  26. PATENTSCOPE (WIPO)
CONTENTS