ChemicalBook Product Catalog Chemical Reagents Organic reagents Polyamines 4-Chloro-1,3-benzenediamine

4-Chloro-1,3-benzenediamine

Product Name4-Chloro-1,3-benzenediamine
CAS5131-60-2
MFC6H7ClN2
MW142.59
EINECS225-877-9
MOL File5131-60-2.mol

Chemical Properties

Melting point	87-90 °C (lit.)
Boiling point	232.49°C (rough estimate)
Density	1.2124 (rough estimate)
refractive index	1.5210 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
pka	3.95±0.10(Predicted)
form	powder to crystal
color	White to Gray to Brown
Water Solubility	<0.1 g/100 mL at 19 ºC
InChI	1S/C6H7ClN2/c7-5-2-1-4(8)3-6(5)9/h1-3H,8-9H2
InChIKey	ZWUBBMDHSZDNTA-UHFFFAOYSA-N
SMILES	Nc1ccc(Cl)c(N)c1
CAS DataBase Reference	5131-60-2(CAS DataBase Reference)
NIST Chemistry Reference	1,3-Benzenediamine, 4-chloro-(5131-60-2)
IARC	3 (Vol. 27, Sup 7) 1987
EPA Substance Registry System	4-Chloro-m-p.henylenediamine (5131-60-2)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
RIDADR	UN 1673 6.1/PG 3
WGK Germany	3
RTECS	SS8800000
TSCA	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29215900
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Hazardous Substances Data	5131-60-2(Hazardous Substances Data)

MSDS

Provider	Language
4-Chloro-1,3-phenylenediamine	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

Crystals. Soluble in ethanol; slightly soluble in water; insoluble in petroleum ether.

Uses

This compound has uses in dye production and in rubber processing.

Uses

4-Chloro-1,3-diaminobenzene has been used to study the mutagenic effect of phenylenediamines hair chemicals on Salmonella typhimurium TA 102.

Definition

ChEBI: 4-Chloro-meta-phenylenediamine is a member of monochlorobenzenes.

General Description

Gray powder or dark purple solid.

Air & Water Reactions

4-Chloro-1,3-benzenediamine is sensitive to prolonged exposure to light and air. Insoluble in water.

Reactivity Profile

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: 4-Chloro-1,3-benzenediamine is a positive animal carcinogen and suspected human carcinogen.

Fire Hazard

Flash point data for 4-Chloro-1,3-benzenediamine are not available; however, 4-Chloro-1,3-benzenediamine is probably combustible.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also AROMATIC AMINES.

Synthesis

6283-25-6

5131-60-2

General method: 2-chloro-5-nitroaniline (1 mmol), Pd/C (5% w/w) and methanol (5 mL) were mixed in a reaction vial and hydrazine hydrate (10 mmol) was added to the mixture. The reaction system was heated at reflux at 80 °C for 5 min. Upon completion of the reaction, the mixture was filtered while hot to remove the catalyst and the filtrate was concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography to give 4-chloro-1,3-benzenediamine.

References

[1] RSC Advances, 2016, vol. 6, # 23, p. 19331 - 19340
[2] Synlett, 2014, vol. 25, # 10, p. 1403 - 1408
[3] Patent: WO2006/40568, 2006, A1. Location in patent: Page/Page column 70
[4] Catalysis Communications, 2016, vol. 84, p. 25 - 29

4-Chloro-1,3-benzenediamine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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