2-Chloroaniline Chemical Properties

Melting point:

0-3 °C

Boiling point:

208-210 °C(lit.)

Density 

1.213 g/mL at 25 °C(lit.)

vapor density 

4.41 (vs air)

vapor pressure 

0.5 hPa (20 °C)

refractive index 

n20/D 1.589

Flash point:

98 °C

storage temp. 

Store below +30°C.

solubility 

water: soluble5.13g/L at 20°C

form 

Liquid

pka

2.65(at 25℃)

color 

Clear pale yellow to brown

Odor

Characteristic odour

explosive limit

2.4-14.2%(V)

Water Solubility 

5.13 g/L (20 ºC)

Merck 

14,2118

BRN 

606077

LogP

1.72 at 20℃ and pH6-8

CAS DataBase Reference

95-51-2(CAS DataBase Reference)

NIST Chemistry Reference

o-Chloroaniline(95-51-2)

EPA Substance Registry System

o-Chloroaniline (95-51-2)

Safety Information

Hazard Codes 

T,N,F

Risk Statements 

23/24/25-33-50/53-39/23/24/25-11-52/53

Safety Statements 

28-36/37-45-60-61-28A-16

RIDADR 

UN 2019 6.1/PG 2

WGK Germany 

2

RTECS 

BX0525000

F 

8-10-23

Autoignition Temperature

>500 °C

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29214210

Hazardous Substances Data

95-51-2(Hazardous Substances Data)

MSDS

• Language:English Provider:Fast yellow GC base
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloroaniline Usage And Synthesis

Chemical Properties

clear pale yellow to brown liquid with ammonia odor. darkens on exposure to air. almost insoluble in water, soluble in acids and most common organic solvents.

Uses

2-Chloroaniline is the raw material of herbicide green sulfuron, and also an important dye intermediate. It is the color base of ice dyeing dyestuff and can also be used as the diazo component of azo dyestuff to produce acid black, acid blue and organic color precipitation water solid yellow R, permanent red FR, Hansa yellow HR, etc.

Uses

2-Chloroaniline used as petroleum solvents. It is used in biological studies to evaluate the mutagenicity and carcinogenicity of Salmonella typhimurium. Used as a Intermediates for dyestuff, pigment and specialty chemicals. 2-Chloroaniline is widely used in polymer, rubber, pharmaceutical and dye industries.

Preparation

The synthesis method of 2-chloroaniline is to reflux 2-nitrochlorobenzene with iron filings, dilute hydrochloric acid and water for 6~8h, distill to get crude product, and then distill to get finished product.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 2718, 1974 DOI: 10.1021/jo00932a011
Tetrahedron Letters, 26, p. 3277, 1985 DOI: 10.1016/S0040-4039(00)98171-1

General Description

Clear amber liquid with an amine odor. Occurs in both alpha and beta forms.

Air & Water Reactions

Sensitive to prolonged exposure to air and darkens on exposure to light. Insoluble in water.

Reactivity Profile

2-Chloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.

Hazard

Toxic by ingestion.

Fire Hazard

2-Chloroaniline is combustible.

Safety Profile

Poison by skin contact, ingestion, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also ANILINE DYES.

Purification Methods

Free it from small amounts of the p-isomer by dissolving in one equivalent of H2SO4 and steam distilling. The p-isomer remains behind as the sulfate. [Sidgwick & Rubie J Chem Soc 1013 1921.] An alternative method is to dissolve it in warm 10% HCl (11mL/g of amine) and on cooling, o-chloroaniline hydrochloride separates out. The latter can be recrystallised until the acetyl derivative has a constant melting point (m 90o). (In this way, yields are better than via the recrystallisation of the picrate from EtOH or of the acetyl derivative from pet ether.) [King & Orton J Chem Soc 1377 1911]. [Beilstein 12 III 1281, 12 IV 1115.]

2-Chloroaniline(95-51-2)Related Product Information

• 2-Chlorophenethylamine
• 2-Chlorobenzoic acid
• 2-Chlorotoluene
• 2-Chlorobenzaldehyde
• 2-Chlorobenzoyl chloride
• Quintozine
• 2,3-Dichloronitrobenzene
• 2,5-DICHLOROPHENYL ISOCYANATE
• 2-CHLOROPHENYL ISOTHIOCYANATE
• 2-Nitrochlorobenzene
• 2,3-Dichlorophenyl isocyanate
• 2,6-Dichlorophenyl isocyanate
• TECNAZENE
• 2-Chlorophenyl isocyanate
• 2,3,4-TRICHLORONITROBENZENE
• 1-(2-Chlorophenyl)-2-thiourea
• 2,3,4,5-Tetrachloronitrobenzene
• ACID YELLOW 34 (C.I. 18890)