3-Chloroaniline Chemical Properties

Melting point:

−11-−9 °C(lit.)

Boiling point:

95-96 °C11 mm Hg(lit.)

Density 

1.206 g/mL at 25 °C(lit.)

vapor pressure 

1 mm Hg ( 63.5 °C)

refractive index 

n20/D 1.594(lit.)

Flash point:

255 °F

storage temp. 

Store below +30°C.

solubility 

6.2g/l

form 

Liquid

pka

3.46(at 25℃)

color 

Clear pale yellow to brown

PH

7.3 (H2O)(saturated aqueous solution)

Odor

Characteristic odour

Water Solubility 

6.8 g/L (20 ºC)

Decomposition 

190°C

Merck 

14,2118

BRN 

605969

Dielectric constant

13.4（19℃）

Stability:

Material darkens in storage with no loss in purity, Material Darkens In Storage

LogP

0.77-2.03 at 25-30℃

CAS DataBase Reference

108-42-9(CAS DataBase Reference)

NIST Chemistry Reference

m-Chloroaniline(108-42-9)

EPA Substance Registry System

m-Chloroaniline (108-42-9)

Safety Information

Hazard Codes 

T,N

Risk Statements 

23/24/25-33-50/53

Safety Statements 

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

RIDADR 

UN 2019 6.1/PG 2

WGK Germany 

2

RTECS 

BX0350000

F 

8-10-23

Autoignition Temperature

705 °C

Hazard Note 

Toxic

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29214210

Hazardous Substances Data

108-42-9(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 256 mg/kg LD50 dermal Rat 250 mg/kg

MSDS

• Language:English Provider:1-Amino-3-chlorobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Chloroaniline Usage And Synthesis

Description

m-Chloroaniline is used as an intermediate for pesticides, pharmaceuticals, and dyes. It is produced by lowpressure hydrogenation of 3-chloronitrobenzene in the liquid phase with noble metal and/or noble metal sulfide catalysts. The addition of metal oxides to the reaction helps avoid dehalogenation. The yield is approximately 98 %.

Chemical Properties

3-Chloroaniline is a clear pale yellow to brown liquid, which becomes darker during storage, insoluble in water, but soluble in ethanol, ether and acid solution.

Application

3-Chloroaniline is the intermediate of the herbicide chloraniline, and the intermediate of the pharmaceutical diuretic antihypertensive drug hydrochlorothiazide, and can be used to produce azo dyes.
3-Chloroaniline was the only aniline compound to increase plasmaALT/GPT activity at 48 h. It is employed in the bioaugmentation of activated sludge.

Uses

3-Chlorobenzenamine is used in the synthesis of pyrimidoazepine analogs as serotonin 5-HT2A and 5-HT2C receptor ligands for the treatment of obesity. Also used in the synthesis of novel COX-2 inhibito rs.

Preparation

3-Chloroaniline is obtained by reducing 3-Nitrochlorobenzene with iron powder in the presence of ferrous sulfate.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 7313, 1995 DOI: 10.1016/0040-4039(95)01474-V

General Description

Colorless to light amber liquid with a sweet odor.

Air & Water Reactions

Sensitive to prolonged exposure to air and light and tends to darken during storage. Insoluble in water.

Reactivity Profile

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

Fire Hazard

3-Chloroaniline is combustible.

Flammability and Explosibility

Non flammable

Safety Profile

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

3-Chloroaniline(108-42-9)Related Product Information

• 2-Chloroaniline
• 1-Chloro-3-nitrobenzene
• 6-Aminocaproic acid
• 2,5-Dichloroaniline
• Tris(hydroxymethyl)aminomethane
• Metanilic acid
• 3-Aminobenzenesulfonamide
• 3-Aminoacetophenone
• Glycine
• 3-Aminophenol
• 1,3-Dichlorobenzene
• EC 2.6.1.2
• 2,6-Dichloroaniline
• 3,4-Dichloroaniline
• Chlorobenzene
• ALTRENOGEST
• Acetaminophen
• p-Anisidine