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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:24:27 UTC

Update Date

2021-09-26 22:55:26 UTC

HMDB ID

HMDB0246383

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Chloro-2-methylaniline

Description

4-chloro-2-methylaniline, also known as 4-chloro-O-toluidine or 2-amino-5-chlorotoluene, belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group. Based on a literature review very few articles have been published on 4-chloro-2-methylaniline. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-chloro-2-methylaniline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Chloro-2-methylaniline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Chloro-O-toluidine	Kegg
2-Amino-5-chlorotoluene	Kegg
4-Chloro-2-methylaniline hydrochloride	MeSH
4-Chloro-2-toluidine	MeSH
4-Chloro-2-toluidine hydrochloride	MeSH
p-Chloro-O-toluidine	MeSH
p-Chloro-O-toluidine hydrochloride	MeSH

Chemical Formula

C₇H₈ClN

Average Molecular Weight

141.6

Monoisotopic Molecular Weight

141.034527

IUPAC Name

4-chloro-2-methylaniline

Traditional Name

4-chloro-o-toluidine

CAS Registry Number

Not Available

SMILES

CC1=CC(Cl)=CC=C1N

InChI Identifier

InChI=1S/C7H8ClN/c1-5-4-6(8)2-3-7(5)9/h2-4H,9H2,1H3

InChI Key

CXNVOWPRHWWCQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Toluenes

Direct Parent

Aminotoluenes

Alternative Parents

Substituents

Aminotoluene
Aniline or substituted anilines
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:82276 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.36	ALOGPS
logP	2.26	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	3.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.6 m³·mol⁻¹	ChemAxon
Polarizability	14.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	130.156	30932474
DeepCCS	[M-H]-	127.837	30932474
DeepCCS	[M-2H]-	164.076	30932474
DeepCCS	[M+Na]+	138.928	30932474
AllCCS	[M+H]+	126.9	32859911
AllCCS	[M+H-H2O]+	122.2	32859911
AllCCS	[M+NH4]+	131.3	32859911
AllCCS	[M+Na]+	132.6	32859911
AllCCS	[M-H]-	124.3	32859911
AllCCS	[M+Na-2H]-	126.4	32859911
AllCCS	[M+HCOO]-	128.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-2-methylaniline	CC1=CC(Cl)=CC=C1N	2061.2	Standard polar	33892256
4-Chloro-2-methylaniline	CC1=CC(Cl)=CC=C1N	1234.2	Standard non polar	33892256
4-Chloro-2-methylaniline	CC1=CC(Cl)=CC=C1N	1289.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-2-methylaniline,1TMS,isomer #1	CC1=CC(Cl)=CC=C1N[Si](C)(C)C	1457.9	Semi standard non polar	33892256
4-Chloro-2-methylaniline,1TMS,isomer #1	CC1=CC(Cl)=CC=C1N[Si](C)(C)C	1385.1	Standard non polar	33892256
4-Chloro-2-methylaniline,1TMS,isomer #1	CC1=CC(Cl)=CC=C1N[Si](C)(C)C	1558.1	Standard polar	33892256
4-Chloro-2-methylaniline,2TMS,isomer #1	CC1=CC(Cl)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1499.1	Semi standard non polar	33892256
4-Chloro-2-methylaniline,2TMS,isomer #1	CC1=CC(Cl)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1580.4	Standard non polar	33892256
4-Chloro-2-methylaniline,2TMS,isomer #1	CC1=CC(Cl)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1589.1	Standard polar	33892256
4-Chloro-2-methylaniline,1TBDMS,isomer #1	CC1=CC(Cl)=CC=C1N[Si](C)(C)C(C)(C)C	1682.8	Semi standard non polar	33892256
4-Chloro-2-methylaniline,1TBDMS,isomer #1	CC1=CC(Cl)=CC=C1N[Si](C)(C)C(C)(C)C	1608.6	Standard non polar	33892256
4-Chloro-2-methylaniline,1TBDMS,isomer #1	CC1=CC(Cl)=CC=C1N[Si](C)(C)C(C)(C)C	1741.1	Standard polar	33892256
4-Chloro-2-methylaniline,2TBDMS,isomer #1	CC1=CC(Cl)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1956.8	Semi standard non polar	33892256
4-Chloro-2-methylaniline,2TBDMS,isomer #1	CC1=CC(Cl)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1995.6	Standard non polar	33892256
4-Chloro-2-methylaniline,2TBDMS,isomer #1	CC1=CC(Cl)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1837.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-2-methylaniline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3900000000-cc5c291ab57941244957	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-2-methylaniline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 10V, Positive-QTOF	splash10-0006-0900000000-58e052ba5ae485c6b5f5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 20V, Positive-QTOF	splash10-0006-0900000000-66315826c38da0175c76	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 40V, Positive-QTOF	splash10-02ei-9500000000-bdeda807821aecb44bed	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 10V, Negative-QTOF	splash10-0006-0900000000-cadfd76bc85c567e98f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 20V, Negative-QTOF	splash10-0006-0900000000-5d92415d51c79d60cc26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 40V, Negative-QTOF	splash10-0udl-5900000000-703d9b67b509588980f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 10V, Positive-QTOF	splash10-0006-0900000000-4ee5202fd2d220533703	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 20V, Positive-QTOF	splash10-0006-1900000000-5990ef3b9ee16c28d661	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 40V, Positive-QTOF	splash10-004i-9200000000-ad4cf54e5b30cc9deba1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 10V, Negative-QTOF	splash10-0006-3900000000-cba896363d121973de72	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 20V, Negative-QTOF	splash10-001i-9400000000-edbe0b404e2cad1bec8c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-2-methylaniline 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6981

KEGG Compound ID

C19169

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1592511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-Chloro-2-methylaniline (HMDB0246383)

MOL for HMDB0246383 (4-Chloro-2-methylaniline)

3D MOL for HMDB0246383 (4-Chloro-2-methylaniline)

3D SDF for HMDB0246383 (4-Chloro-2-methylaniline)

3D-SDF for HMDB0246383 (4-Chloro-2-methylaniline)

PDB for HMDB0246383 (4-Chloro-2-methylaniline)

3D PDB for HMDB0246383 (4-Chloro-2-methylaniline)

SMILES for HMDB0246383 (4-Chloro-2-methylaniline)

INCHI for HMDB0246383 (4-Chloro-2-methylaniline)

Structure for HMDB0246383 (4-Chloro-2-methylaniline)

3D Structure for HMDB0246383 (4-Chloro-2-methylaniline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra