3-Chloro-2-methylaniline

3-Chloro-2-methylaniline Basic information
Synthesis
Product Name:3-Chloro-2-methylaniline
Synonyms:2-Chloro-2-Methyl Aniline;3-Chloro-2-methylaniline, 98+%;3-Chlor-o-toluidin;3-chloro-2-toluidin;3-CHLORO-2-METHYLANILINE / 2-AMINO-6-CHLOROTOLUENE;3-chloro-o-toluidin;6-Chloro-2-amino-1-methylbenzene;6-chloro-ortho-toluidine
CAS:87-60-5
MF:C7H8ClN
MW:141.6
EINECS:201-756-6
Product Categories:API intermediates;Aromatic Hydrocarbons (substituted) & Derivatives
Mol File:87-60-5.mol
3-Chloro-2-methylaniline Structure
3-Chloro-2-methylaniline Chemical Properties
Melting point 2 °C (lit.)
Boiling point 115-117 °C/10 mmHg (lit.)
density 1.185 g/mL at 25 °C (lit.)
refractive index n20/D 1.588(lit.)
Fp >230 °F
storage temp. Store below +30°C.
solubility 4.5g/l
form Liquid
pkapK1:2.49(+1) (25°C)
Specific Gravity1.19
color Clear yellow to red or red-brown
Water Solubility 1g/L at 20℃
BRN 471697
InChIKeyZUVPLKVDZNDZCM-UHFFFAOYSA-N
LogP2.4
CAS DataBase Reference87-60-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenamine, 3-chloro-2-methyl-(87-60-5)
EPA Substance Registry System3-Chloro-2-methylaniline (87-60-5)
Safety Information
Hazard Codes C,N,Xn
Risk Statements 22-34-43-51/53-36/37/38
Safety Statements 26-36/37/39-45-61-37/39
RIDADR UN 3429 6.1/PG 3
WGK Germany 2
RTECS XU4760000
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29214300
Hazardous Substances Data87-60-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Fast Scarlet TR BaseEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
3-Chloro-2-methylaniline Usage And Synthesis
SynthesisIt is obtained by chlorination and reduction of o-nitrotoluene.
1. Chlorination reaction
In o-nitrotoluene, add 2% ferric chloride as a catalyst, pass chlorine gas at 50-60 ° C until the relative density of the reaction solution reaches 1.27-1.29 (50 ° C), wash with 5% hydrochloric acid, and then Wash with water, and finally adjust pH to 7 with liquid caustic soda. Divide the water layer, evaporate the water, carry out vacuum distillation, collect 120-150 ℃ (5.33-8.0kPa) fractions, crystallize by cooling and filter to obtain 2-chloro-6-nitrotoluene.
2. Reduction reaction
Add hydrochloric acid and iron powder to the reaction pot, stir and heat to 90°C, slowly add melted 2-chloro-6-nitrotoluene, complete the addition, and reflux for 3 hours. Cooling, adding liquid alkali to adjust pH to 8, steam distillation to obtain 3-chloro-o-toluidine.
Chemical PropertiesThe chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.
Chemical Propertiesclear yellow to red or red-brown liquid
Uses3-Chloro-2-Methylaniline can be used for dyeing cotton, viscose, silk, nylon and acetate, as well as printing on cotton. It is mainly used for dyeing red, such as coupling with chromophenol AS, AS-BO, AS-ITR, etc.
UsesIntermediate.
PreparationBy 1-Methyl-2-nitrobenzene chlorination byproducts 3-Chloro-2-methylbenzenamine?reduction.
HazardToxic by ingestion or inhalation.
Safety ProfilePoison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also other chloro toluidine entries.
Potential ExposureMost of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to kill birds. It is marketed as pelleted bait for control of bird populations.
IncompatibilitiesIncompatible with oxidizers, strong acids; chloroformates, and acid anhydrides, isocyanates, aldehydes forming fire and explosive hazards.
3-Chloro-2-methylaniline Preparation Products And Raw materials
Raw materialsIron–>Ferric chloride–>2-Nitrotoluene–>2-Chloro-6-nitrotoluene–>Sodium propanolate–>4-CHLORO-2-METHYL-1H-INDOLE–>2-Nitrotoluene–>3-Chloro-2-methylaniline
Preparation Products2,6-Dichlorotoluene–>Quinclorac–>3-CHLORO-2-METHYLBENZONITRILE–>7-Dimethylamino-4-methylcoumarin–>pigment yellow 155–>2-Chloro-6-fluorotoluene–>7-CHLORO-8-METHYLQUINOLINE–>3-CHLORO-2-METHYLPHENYL ISOTHIOCYANATE–>3-Amino-2-methylphenylboronic acid, pinacol ester–>Clonixin–>4-CHLORO (1H)INDAZOLE–>3-Chloro-2-methylbenzoic acid–>3-Chloro-2-methylaniline–>Mordant Violet 10–>N-(3-CHLORO-2-METHYL-PHENYL)-2,2-DIMETHYL-PROPIONAMIDE–>7-CHLORO-8-METHYL-2-PHENYLQUINOLINE-4-CARBOXYLICACID

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