Description
3,4-Dichloroaniline, 1-amino3,4- dichlorobenzene, is a gray
to dark-brown crystalline solid at room temperature. It is
used as an intermediate for pesticides and dyes
and is produced by catalytic hydrogenation of
3,4-dichloronitrobenzene with noble metal catalysts under pressure. Various types of additives
prevent dehalogenation during production and
reactors must be fabricated with special steel
alloys to inhibit corrosion.
Description
3,4-Dichloroaniline, 1-amino-
3,4- dichlorobenzene, is a gray
to dark-brown crystalline solid at room temperature. It is
used as an intermediate for pesticides and dyes
and is produced by catalytic hydrogenation of
3,4-dichloronitrobenzene with noble metal catalysts
under pressure. Various types of additives
prevent dehalogenation during production and
reactors must be fabricated with special steel
alloys to inhibit corrosion .
Chemical Properties
brown solid
Uses
3,4-Dichloroaniline is used as an intermediate for pesticides and dyes.
Uses
3,4-Dichloroaniline is used in the preparation of the herbicide propanil (P760840).
Uses
3,4-Dichloroaniline may be employed as derivatization reagent for the HPLC analysis of perfluorooctanoic acid (PFOA).
Definition
ChEBI: A dichloroaniline having the two chloro-substituents at the 3- and 4-positions.
Preparation
3,4-Dichloroaniline is produced by catalytic hydrogenation of 3,4-dichloronitrobenzene with noble metal catalysts under pressure. Various types of additives prevent dehalogenation during production and reactors must be fabricated with special steel alloys to inhibit corrosion.
General Description
Light tan to dark gray crystals or brown solid. Melting point 71-72°C.
Air & Water Reactions
Sensitive to prolonged exposure to heat, light and air. Darkens in storage. Insoluble in water.
Reactivity Profile
3,4-Dichloroaniline is incompatible with oxidizing agetns, acids, acid chlorides and acid anhydrides. 3,4-Dichloroaniline can decompose at low pH. Hydrochloric acid accelerates decomposition. Reacts at temperatures above 356°F in the presence of ferric chloride .
Fire Hazard
3,4-Dichloroaniline is combustible.
Metabolic pathway
The basidiomycete Filoboletus sp. TA9054
metabolizes 3,4-dichloroaniline and forms several
condensation products on solid media and in liquid
culture, and no oligomers are produced. Six
metabolites are identified as 3,3'-4,4'-
tetrachloroazobenzene, 4-(3,4-dichloroanilino)-3,3',4' -
trichloroazobenzene, 4-[(3,4-dichloroanilino)-4-(3,4-
dichloroanilino)]-3,3'4'-trichloroazobenzene, 2-(3,4-
dichloroanilino)-N-(3,4-dichlorophenyl)-4-
(chlorophenylene), 6-(3,4-dichloroanilino)-N-(3,4-
dichlorophenyl)-4-(chlorophenylene), and 3,5-bis(3,4-
dichloroanilino)-1,4-chlorobenzoquinone.
Purification Methods
Crystallise the aniline from MeOH. [Beilstein 12 IV 1257.]
