2,4,6-Trichloroaniline Property

Melting point:

73-75 °C (lit.)

Boiling point:

262 °C (lit.)

Density 

1.6807 (rough estimate)

vapor pressure 

0-0.631Pa at 25℃

refractive index 

1.6300 (estimate)

Flash point:

262°C

storage temp. 

Storage temperature: no restrictions.

solubility 

0.039g/l slightly soluble

pka

0.07±0.10(Predicted)

color 

Needles or liquid from pet ether

Water Solubility 

<0.1 g/100 mL at 21.5 ºC

BRN 

879568

Stability:

Stable, but may be light or air sensitive. Incompatible with acids, acid chlorides, acid anhydrides, chloroformates, strong oxidizing agents.

InChIKey

NATVSFWWYVJTAZ-UHFFFAOYSA-N

LogP

3.648-3.69 at 25℃

CAS DataBase Reference

634-93-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 2,4,6-trichloro-(634-93-5)

EPA Substance Registry System

2,4,6-Trichloroaniline (634-93-5)

Safety

Hazard Codes 

T,N

Risk Statements 

23/24/25-33-50/53

Safety Statements 

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

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

BZ0250000

Hazard Note 

Toxic

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29214200

Hazardous Substances Data

634-93-5(Hazardous Substances Data)

Toxicity

LD50 orl-rat: 2400 mg/kg GISAAA 55(6),86,90

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H331Toxic if inhaled

H373May cause damage to organs through prolonged or repeated exposure

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P311Call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

2,4,6-Trichloroaniline Chemical Properties,Usage,Production

Genotoxicity

Limited information is available regarding the potential genotoxicity of 2,4,6-trichloroaniline. 2,4,6-Trichloroaniline did not induce mutations in Salmonella typhimurium strains TA98, TA100, or TA1537 in the presence or absence of metabolic activation in plate-incorporation assays; microsomal-suspension assays using the same strains and metabolic-activation preparations were also negative. However, using the preincubation method, 2,4,6-trichloroaniline tested positive for mutagenicity in Salmonella and Escherichia coli (strains not specified). 2,4,6-Trichloroaniline tested negative in the Salmonella umu (SOS response) assay and failed to induce DNA repair in rat hepatocytes. In vivo, 2,4,6-trichloroaniline was mutagenic in the wing spot test in Drosophila. Rats treated orally with 2,4,6-trichloroaniline at 40 mg/kg-day (but not 0.4 or 4 mg/kg-day) for 6 months showed a small but statistically significant increase (p < 0.05) in the number of bone marrow cells containing chromosomal aberrations when compared with controls (1.6% vs. 0.4%, respectively); however, this study did not provide any study design details.

Description

Trichloroaniline is particularly important as a chemical intermediate in manufacturing many benzene derivatives and other organic compounds. For instance, 2,4,6-trichloroaniline is an essential precursor of 1,3,5-trichlorobenzene. The latter has been extensively studied and developed for insecticides and fungicides. It, in turn, is a precursor of trichlorodinitrobenzene, which is especially important in combatting crop diseases and is an intermediate for dyestuffs. In military applications, 2,4,6-trichloroaniline is utilized for the preparation of insensitive energetic material that is employed in several Navy weapons systems. The synthesis of 2,4,6-trichloroaniline has almost invariably been accomplished by chlorinating aniline with chlorine or sulfuryl chloride.

Chemical Properties

fine purple fibres

Uses

2,4,6-trichloroaniline is important as an intermediate in the manufacture of benzene derivatives, including 1,3,5-trichlorobenzene and is useful in the formation of fungicides, mono-azo dyestuffs, and the preparation of hexachlorodiphenyl urea.
Tetrachloronitrobenzene was prepared from 2:4:6-trichloroaniline,which was converted by a Sandmeyer reaction into 1:2:3:5- tetrachlorobenzene.

Preparation

2,4,6-Trichloroaniline can be prepared by reaction of dry aniline with chlorine gas while in a anhydrous solution of carbon tetrachloride. 2,4,6-Trichloroaniline precipitates from solution as a white solid. If water is introduced to the solution the white material will polymerize to form aniline black.
Process for the preparation of 2,4,6-trichloroaniline

General Description

Long needles or fine, light purple fibers.

Air & Water Reactions

2,4,6-Trichloroaniline may be sensitive to exposure to light and air. Insoluble in water.

Reactivity Profile

2,4,6-Trichloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates, and strong oxidizing agents. .

Fire Hazard

Flash point data for 2,4,6-Trichloroaniline are not available. 2,4,6-Trichloroaniline is probably combustible.

Safety Profile

Moderately toxic by ingestion.Irritant. Questionable carcinogen with experimentalcarcinogenic data. Mutation data reported. When heatedto decomposition it emits very toxic fumes of Clí andNOx.

Purification Methods

Crystallise the aniline from ligroin. The benzoyl derivative has m 174o (from EtOH). [Beilstein 12 H 627, 12 IV 1281.]