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3-Chloro-4-metdylaniline is a chemical compound with a chlorinated aromatic ring.
3-Chloro-4-metdylaniline is a metabolite of the herbicide atrazine, which has been found to produce toxic effects in humans and animals.
3-Chloro-4-metdylaniline has been shown to disrupt energy metabolism in mammalian cells through its interaction with mitochondrial respiratory chain complexes I and II.
CAS: 95-74-9
MF: C7H8ClN
MW: 141.6
EINECS: 202-446-3
Synonyms
CPT;3-amino-2-chlorotoluene;3-CHLORO-P-TOLUIDINE;3-cpt;3-CHLORO-4-METHYLANILINE;3-chloro-4-methyl-benzenamine;AKOS BBS-00003549;4-AMINO-2-CHLOROTOLUENE;3-Chloro-4-methylaniline;95-74-9;2-Chloro-4-aminotoluene;3-CHLORO-P-TOLUIDINE;4-Amino-2-chlorotoluene;Benzenamine, 3-chloro-4-methyl-;3-Chloro-4-methylbenzenamine;3-Chloro-4-methylphenylamine;4-Methyl-3-chloroaniline;1-Amino-3-chloro-4-methylbenzene;p-Toluidine, 3-chloro-;NCI-C02040;DRC 1339;DRC 1347;NSC 96620;DTXSID0020286;CHEBI:37824;32Y306W7BQ;DKC 1347;NSC-96620;DTXCID60286;202-446-3;3-chloro-4-methyl-phenylamine;MFCD00007773;3-?Chloro-?4-?methylaniline;3-chloro-4-methyl aniline;CAS-95-74-9;CCRIS 152;HSDB 2060;EINECS 202-446-3;3-chloro-4-methyl-aniline;BRN 0636511;UNII-32Y306W7BQ;Aniline, 3-chloro-4-methyl-;827571-80-2;3-chloro-4-toluidine;3-chloro 4-methylaniline;2-chloro-4-amino-toluene;EC 202-446-3;WLN: ZR CG D1;3-chloranyl-4-methyl-aniline;4-12-00-01985 (Beilstein Handbook Reference);MLS002303000;SCHEMBL349538;SCHEMBL1805666;SCHEMBL3956811;SCHEMBL9410515;CHEMBL1374337;SCHEMBL29739515;2-Chloro-4-aminotoluene, 98%;3-Chloro-4-methylaniline, 98%;HMS3055G10;CS-M1324;NSC96620;STR02553;Tox21_201871;Tox21_302755;SBB004152;STK943762;AKOS000119158;FC6432;4-AMINO-2-CHLOROTOLUENE [HSDB];NCGC00091083-01;NCGC00091083-02;NCGC00256599-01;NCGC00259420-01;SMR001252231;TS-01846;DB-024297;NS00005824;ST45255297;EN300-18377;D77417;A845453;Q7602061;Z57127543;F2190-0474;3-Chloro-4-methylaniline, PESTANAL(R), analytical standard;InChI=1/C7H8ClN/c1-5-2-3-6(9)4-7(5)8/h2-4H,9H2,1H
3-Chloro-4-metdylaniline has also been found to cause tubule cell death in the kidneys of rats, as well as liver lesions in mice.
A monochloroaniline that is p-toluidine in which one of the hydrogens that is meta to the amino group is replaced by a chlorine.
3-Chloro-4-metdylaniline is a monochloroaniline that is p-toluidine in which one of the hydrogens that is meta to the amino group is replaced by a chlorine.
3-Chloro-4-metdylaniline has a role as an avicide.
3-Chloro-4-metdylaniline is a chloroaniline and a member of monochlorobenzenes.
3-Chloro-4-metdylaniline is functionally related to a p-toluidine.
3-Chloro-4-metdylaniline, is an aromatic amine characterized by the presence of a chlorine atom and a methyl group attached to a benzene ring.
Specifically, 3-Chloro-4-metdylaniline is located at the meta position (3) and the methyl group at the para position (4) relative to the amino group (-NH2).
This compound typically appears as a solid or liquid, depending on temperature, and is known for its light yellow to brown color.
3-Chloro-4-metdylaniline is soluble in organic solvents but has limited solubility in water.
3-Chloro-4-metdylaniline is primarily used in the synthesis of dyes, pigments, and pharmaceuticals.
3-Chloro-4-metdylaniline exhibits moderate toxicity, and safety precautions should be taken when handling it, as it can cause skin and eye irritation.
Additionally, 3-Chloro-4-metdylaniline is important to note that aromatic amines can be potential carcinogens, necessitating careful management in industrial applications.
Proper storage and disposal methods are essential to minimize environmental impact and health risks.
3-Chloro-4-metdylaniline Chemical Properties
Melting point: 25 °C
Boiling point: 237-238 °C(lit.)
Density: 1.17
Vapor pressure: 4.973-8.666Pa at 25℃
Refractive index: n20/D 1.584(lit.)
Fp: 212 °F
Storage temp.: 2-8°C
Solubility: Chloroform, Methanol (Slightly)
Form: powder to lump to clear liquid
Pka: pK1: 4.05(+1) (25°C)
Color: White or Colorless to Light orange to Yellow
Specific Gravity: 1.167
Water Solubility: 1 g/L (20 ºC)
BRN: 636511
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acids, acid anhydrides, chloroformates, reducing agents.
LogP: 2.27
CAS DataBase Reference: 95-74-9(CAS DataBase Reference)
NIST Chemistry Reference: Benzenamine, 3-chloro-4-methyl-(95-74-9)
EPA Substance Registry System: 3-Chloro-4-metdylaniline (95-74-9)
The chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.
Uses
3-Chloro-4-metdylaniline has been used in the preparation of 2-chloro-4-cyanotoluene by Sandmeyer reaction with cuprous cyanide.
Reactivity Profile
3-Chloro-4-metdylaniline may be sensitive to prolonged exposure to air and light.
3-Chloro-4-methylaniline may react with oxidizing agents.
3-Chloro-4-methylaniline is incompatible with acids, acid chlorides, acid anhydrides and chloroformates.
3-Chloro-4-methylaniline is also incompatible with reducing agents.
Synthesis
General procedure for the synthesis of 3-chloro-p-toluidine from 2-chloro-4-nitrotoluene: General method: Nitro compounds (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed.
Subsequently, a 2N aqueous hydrochloric acid solution was slowly added to the reaction mixture.
The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3) solution.
Next, 3-Chloro-4-metdylaniline was extracted three times with saturated aqueous sodium bicarbonate solution.
The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure.
Finally, the crude product was purified by silica gel column chromatography to obtain the target product 3-chloro-p-toluidine.
