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N-(tert-Butoxycarbonyl)-L-phenylalanine

PubChem CID
77857
Structure
N-(tert-Butoxycarbonyl)-L-phenylalanine_small.png
N-(tert-Butoxycarbonyl)-L-phenylalanine_3D_Structure.png
Molecular Formula
Synonyms
  • 13734-34-4
  • Boc-Phe-OH
  • Boc-L-phenylalanine
  • N-(tert-Butoxycarbonyl)-L-phenylalanine
  • Boc-phenylalanine
Molecular Weight
265.30 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-11
  • Modify:
    2025-01-18

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-(tert-Butoxycarbonyl)-L-phenylalanine.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Boc-Phe-OH
Sequence
F
HELM
PEPTIDE1{[CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O]}$$$$
IUPAC
N-tert-butoxycarbonyl-L-phenylalanine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C14H19NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

ZYJPUMXJBDHSIF-NSHDSACASA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C14H19NO4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 Deprecated CAS

92761-90-5

3.3.3 European Community (EC) Number

3.3.4 ChEMBL ID

3.3.5 DSSTox Substance ID

3.3.6 Nikkaji Number

3.3.7 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
265.30 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
265.13140809 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
265.13140809 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
75.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
316
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
1
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)

5 Spectral Information

5.1 Mass Spectrometry

5.1.1 GC-MS

1 of 4
View All
NIST Number
234809
Library
Main library
Total Peaks
83
m/z Top Peak
57
m/z 2nd Highest
148
m/z 3rd Highest
91
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
162236
Library
Replicate library
Total Peaks
121
m/z Top Peak
57
m/z 2nd Highest
148
m/z 3rd Highest
91
Thumbnail
Thumbnail

5.2 IR Spectra

5.2.1 FTIR Spectra

Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
134562
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.2.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Peptides International
Catalog Number
BLF-2068
Lot Number
550425
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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Thumbnail

5.3 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
102186
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Peptides International
Catalog Number
BLF-2068
Lot Number
550425
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Use and Manufacturing

8.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-: INACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
Pictograms displayed are for 66.7% (6 of 9) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 33.3% (3 of 9) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (22.2%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, 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 9 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 3 of 9 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 4 notifications provided by 6 of 9 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.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (22.2%)

Skin Irrit. 2 (33.3%)

Eye Irrit. 2A (66.7%)

STOT SE 3 (33.3%)

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Thieme References

10.4 Wiley References

10.5 Nature Journal References

10.6 Chemical Co-Occurrences in Literature

10.7 Chemical-Gene Co-Occurrences in Literature

10.8 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 ChemIDplus

13.2 ChEMBL Target Tree

13.3 UN GHS Classification

13.4 NORMAN Suspect List Exchange Classification

13.5 EPA DSSTox Classification

13.6 EPA TSCA and CDR Classification

13.7 EPA Substance Registry Services Tree

13.8 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. 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/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-
    https://comptox.epa.gov/dashboard/DTXSID90884634
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. Nature Chemistry
  9. 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
    L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-
    http://www.nist.gov/srd/nist1a.cfm
  10. SpectraBase
    (2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoic acid
    https://spectrabase.com/spectrum/GjrVU6Ql6t8
    N-tert-Butoxycarbonyl-L-phenylalanine
    https://spectrabase.com/spectrum/2zUCV3rdqb6
  11. Springer Nature
  12. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  13. Wikidata
    N-(tert-Butoxycarbonyl)-L-phenylalanine
    https://www.wikidata.org/wiki/Q72510378
  14. Wiley
  15. PubChem
  16. GHS Classification (UNECE)
  17. 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/
  18. EPA Substance Registry Services
  19. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  20. PATENTSCOPE (WIPO)
CONTENTS