ChemicalBook Product Catalog Organic Chemistry Amides Naphthenic amines derivatives 3,4-Dichloroaniline

3,4-Dichloroaniline

Product Name3,4-Dichloroaniline
CAS95-76-1
MFC6H5Cl2N
MW162.02
EINECS202-448-4
MOL File95-76-1.mol

Chemical Properties

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
Henry's Law Constant	6.8×10^-1 mol/(m³Pa) at 25℃, Duchowicz et al. (2020)
Stability	Stable, but darkens in storage. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides.
InChI	1S/C6H5Cl2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2
InChIKey	SDYWXFYBZPNOFX-UHFFFAOYSA-N
SMILES	Nc1ccc(Cl)c(Cl)c1
LogP	2.68 at 20℃
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

Hazard Codes	T,N
Risk Statements	23/24/25-41-43-50/53-51/53-33
Safety Statements	26-36/37/39-45-60-61-36/37-28
RIDADR	UN 1590 (DICHLOROANILINES, LIQUID)
WGK Germany	3
RTECS	BX2625000
F	8
TSCA	TSCA listed
HazardClass	6.1
PackingGroup	II
HS Code	29214210
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 Eye Dam. 1 Skin Sens. 1
Hazardous Substances Data	95-76-1(Hazardous Substances Data)

MSDS

Provider	Language
3,4-Dichlorobenzenamine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

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

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.]

Preparation Products And Raw materials

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