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2,4,6-Trichloroaniline

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CAS:634-93-5
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2,4,6-Trichloroaniline Basic information
Genotoxicity
Product Name:2,4,6-Trichloroaniline
Synonyms:2,4,6-Trichloroaniline, 98.5% 100GR;1-Amino-2,4,6-trichlorobenzene;2,4,6-TRICHLOROANILINE;2,4,6-trichloraniline;2,4,6-trichloro-anilin;2,4,6-trichloro-benzenamin;Aniline, 2,4,6-trichloro-;aniline,2,4,6-trichloro-
CAS:634-93-5
MF:C6H4Cl3N
MW:196.46
EINECS:211-219-8
Product Categories:Alpha sort;Amines;AromaticsPesticides&Metabolites;Chemical Class;Q-ZAlphabetic;TP - TZ
Mol File:634-93-5.mol
2,4,6-Trichloroaniline Structure
2,4,6-Trichloroaniline Chemical Properties
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)
Fp 262°C
storage temp. Storage temperature: no restrictions.
solubility 0.039g/l slightly soluble
pka0.07±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.
InChIKeyNATVSFWWYVJTAZ-UHFFFAOYSA-N
LogP3.648-3.69 at 25℃
CAS DataBase Reference634-93-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenamine, 2,4,6-trichloro-(634-93-5)
EPA Substance Registry System2,4,6-Trichloroaniline (634-93-5)
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 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 Data634-93-5(Hazardous Substances Data)
ToxicityLD50 orl-rat: 2400 mg/kg GISAAA 55(6),86,90
MSDS Information
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2,4,6-Trichloroaniline English
SigmaAldrich English
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2,4,6-Trichloroaniline Usage And Synthesis
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 Propertiesfine purple fibres
Uses2,4,6-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.
Preparation2,4,6-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 DescriptionLong needles or fine, light purple fibers.
Air & Water Reactions2,4,6-Trichloroaniline may be sensitive to exposure to light and air. Insoluble in water.
Reactivity Profile2,4,6-Trichloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates, and strong oxidizing agents. .
Fire HazardFlash point data for 2,4,6-Trichloroaniline are not available. 2,4,6-Trichloroaniline is probably combustible.
Safety ProfileModerately toxic by ingestion.Irritant. Questionable carcinogen with experimentalcarcinogenic data. Mutation data reported. When heatedto decomposition it emits very toxic fumes of Clí andNOx.
Purification MethodsCrystallise the aniline from ligroin. The benzoyl derivative has m 174o (from EtOH). [Beilstein 12 H 627, 12 IV 1281.]
Tag:2,4,6-Trichloroaniline(634-93-5) Related Product Information
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