3,4-Dichloroaniline

CAS NO.：95-76-1
Empirical Formula: C6H5Cl2N
Molecular Weight: 162.02
MDL number: MFCD00007768
EINECS: 202-448-4
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-30 21:22:42

What is 3,4-Dichloroaniline?

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
3,4-Dichloroaniline

The Uses of 3,4-Dichloroaniline

3,4-Dichloroaniline is used as an intermediate for pesticides and dyes.

The Uses of 3,4-Dichloroaniline

3,4-Dichloroaniline is used in the preparation of the herbicide propanil (P760840).

The Uses of 3,4-Dichloroaniline

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.]

Properties of 3,4-Dichloroaniline

Melting point:	69-71 °C(lit.)
Boiling point:	272 °C(lit.)
Density	1,34 g/cm³
vapor pressure	97.5Pa at 78℃
refractive index	1.6140 (estimate)
Flash point:	166 °C
storage temp.	0-6°C
solubility	0.73g/l
pka	2.90±0.10(Predicted)
form	Crystalline Mass and/or Chunks
color	Beige to brown
PH	7.1 (0.8g/l, H2O)
Water Solubility	0.06 g/100 mL
Merck	14,3054
BRN	636837
Stability:	Stable, but darkens in storage. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.
CAS DataBase Reference	95-76-1(CAS DataBase Reference)
NIST Chemistry Reference	Benzenamine, 3,4-dichloro-(95-76-1)
EPA Substance Registry System	3,4-Dichloroaniline (95-76-1)

Safety information for 3,4-Dichloroaniline

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Skull and Crossbones Acute Toxicity GHS06 Environment GHS09
GHS Hazard Statements	H317:Sensitisation, Skin H318:Serious eye damage/eye irritation H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.