2-Chloro-p-toluidine
Basic information
- CAS
615-65-6- Standard SMILES
Cc1ccc(N)c(Cl)c1- InChIKey
XGYLSRFSXKAYCR-UHFFFAOYSA-N- Molecular formula
- C7H8ClN
- Average molar mass
- 141.6 g/mol
- Monoisotopic mass
- 141.03452694
Names & identifiers
- Preferred name
- 2-Chloro-p-toluidine
- IUPAC
- 2-chloro-4-methylaniline
- English name
- 2-Chloro-4-methylaniline
- Molecular formula
- C7H8ClN
- Molecular weight
- 141.6
Names & synonyms
2-Chloro-4-methylaniline615-65-62-CHLORO-P-TOLUIDINE4-Amino-3-chlorotolueneBenzenamine, 2-chloro-4-methyl-p-Toluidine, 2-chloro-4-Methyl-2-chloroaniline2-Chlor-4-toluidinNSC 601202-Chlor-4-toluidin [Czech]CCRIS 2887HSDB 2059
Show more names
oro-4-methyL2-chloro-p-toluidin2-chlor-4-toluidine2-CHLORO-4-TOLUIDINE2-Chloro-4-methylani
3-Chloro-4-aminotoluene1-amino-2-chloro-4-methylbenzeneEINECS 210-440-7K59ISJ2KO1BRN 0774514NSC-60120DTXSID30220833-12-00-02152 (Beilstein Handbook Reference)
Database identifiers
- CAS
615-65-6- PubChem CID
- 12007
- DTXSID
DTXSID3022083- UNII
- K59ISJ2KO1
- EC Number
- 210-440-7
- Nikkaji
- J48.073H
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 26 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 94.9
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials PropertiesOptical coefficient
Density1.151 @ 20 °C
SolubilitySLIGHTLY SOL IN WATER, ACETONE
Boiling Point219 °C @ 732 MM HG
Melting Point7 °C
Refractive IndexINDEX OF REFRACTION: 1.5748 @ 22 °C/D
Physical DescriptionPale yellow liquid; [MSDSonline]
Physicochemical properties
- Melting point
- 7 °C · 7 °C (lit.)
- Boiling point
- 223 · 223-225 °C (lit.)
- Density
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302+H312+H332 (86.7%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryA mutagen and severe skin irritant; [RTECS] Emergency treatment: Methemoglobinemia; Chlorotoluidines may cause hemorrhagic cystitis; [HSDB] An irritant; May induce methemoglobinemia; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (95.6%)
Toxicology
Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Human Toxicity Excerpts
THE TOLUIDINES (BOTH O- AND P-) MAY PRODUCE TRANSIENT HEMATURIA AS WELL AS METHEMOGLOBINEMIA AFTER HEAVY EXPOSURES, BUT CHLORO-DERIVATIVES ARE MORE POTENT IN THIS RESPECT, ESPECIALLY 5-CHLORO-O-TOLUIDINE... /TOLUIDINES/
THE CYSTITIS RELATED TO THESE ANILINE DERIVATIVES HAS NO RELATIONSHIP TO CARCINOGENIC AMINE-RELATED PROCESSES. /CHLOROTOLUIDINES/
...HEMATURIA MAY BE OBSERVED IN MEN HANDLING CHLOROTOLUIDINES. ...MAY BE A HEMORRHAGIC CYSTITIS WITH PAINFUL & FREQUENT MICTURITION. THIS ACUTE PROBLEM... NO LONG TERM SIGNIFICANCE & CLEARS...ON CESSATION... IF...PERSISTS, OTHER PATHOLOGICAL URINARY TRACE PHENOMENA MUST BE CONSIDERED. /CHLOROTOLUIDINES/
Chemistry & industry
Pharmacology
Metabolism/MetabolitesFORMS 2,2'-DICHLORO-4,4'-DIMETHYLAZOBENZENE IN HORSERADISH. KNOWLES ET AL, J ECOL ENT 62: 411 (1969). /FROM TABLE/
Uses & manufacturing
Uses
Used as an intermediate; [HSDB]
INTERMEDIATE
General Manufacturing InformationBenzenamine, 2-chloro-4-methyl-: ACTIVE
Applications
Description2-Chloro-4-methylaniline was used in determination of aniline derivatives in environmental water samples using on-line combination of supported liquid membrane extraction and liquid chromatography. It was also used in determination of amines in environmental water samples by gas chromatography–mass spectrometry. It is an intermediate used to prepare reverse transcriptase inhibitors of HIV-1.
Uses2-Chloro-4-methylaniline is an intermediate used to prepare reverse transcriptase inhibitors of HIV-1.
Uses2-Chloro-4-methylaniline was used in determination of aniline derivatives in environmental water samples using on-line combination of supported liquid membrane extraction and liquid chromatography. It was also used in determination of amines in environmental water samples by gas chromatography–mass spectrometry.
Upstream & downstream products
Downstream products
Related reactions
35 records
Compound notes
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