4-Nitro-o-phenylenediamine Chemical Properties

Melting point:

199-201 °C (lit.)

Boiling point:

276.04°C (rough estimate)

Density 

1.3682 (rough estimate)

refractive index 

1.6910 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

1 N HCl: ethanol, 1:1: soluble50mg/mL

pka

2.06±0.10(Predicted)

form 

Powder

color 

Brown-red

Water Solubility 

1.2 g/L (20 ºC)

Merck 

14,6622

BRN 

608106

Stability:

Stable. Incompatible with strong acids, strong reducing agents, strong oxidizing agents, acid chlorides, acid anhydrides.

InChIKey

RAUWPNXIALNKQM-UHFFFAOYSA-N

CAS DataBase Reference

99-56-9(CAS DataBase Reference)

IARC

3 (Vol. 16, Sup 7) 1987

EPA Substance Registry System

Nitro-o-phenylenediamine (99-56-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43-68-40-36/37/38-20/21/22

Safety Statements 

36/37-45-36-26-22

RIDADR 

2811

WGK Germany 

3

RTECS 

ST2975000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29215119

Hazardous Substances Data

99-56-9(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 681mg/kg

MSDS

• Language:English Provider:3,4-Diaminonitrobenzene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Nitro-o-phenylenediamine Usage And Synthesis

Chemical Properties

This substance is an orange-red powder that can be dissolved in ethanol, acetone, and hydrochloric acid solution, but is not soluble in water.

Uses

4-Nitro-o-phenylenediamine was used to study the in vitro activation of 4-nitro-o-phenylenediamine into a potent mutagen in Salmonella typhimurium strain TA98 .

Definition

ChEBI: 4-nitro-1,2-phenylenediamine is the primary amino compound that is 1,2-phenylenediamine (o-phenylenediamine) substituted at the 4- (para-) position by a nitro group. It is a primary amino compound and a C-nitro compound. It is functionally related to a 1,2-phenylenediamine.

Production Methods

Commercial production of 4-nitro-o-PDA was first reported in the United States in 1946. Two U.S. companies were reported to produce undisclosed amounts of the chemical in 1975. U.S. imports of 4-nitro-o-PDA were reported to be about 1900 kg in 1973 and 1100 kg in 1975. 4-Nitro-o-PDAis used in fur dyes, inks, and semipermanent yellow hair coloring formulations requiring a yellow color component that does not involve the use of hydrogen peroxide in the color development.
Occupational exposure to 4-nitro-o-PDA may occur through inhalation and dermal contact with this compound at workplaces where p-PDA is produced or used. The general population may be exposed to the compound via dermal contact, primarily through the use of hair dyes containing this compound.

Application

4-Nitro-1,2-phenylenediamine is a hair dye constituent with potential mutagenic activity. It is used in oxidation hair dye formulations at a maximum concentration of 1.0 %, which after mixing typically in a 1:1 ratio with hydrogen peroxide just prior to use, corresponds to a concentration of 0.5% upon application.

Preparation

Prepared by reduction of 2,4-dinitroaniline using H2S in ammonia water.

General Description

4-nitro-o-phenylenediamine appears as dark red needles or red solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Nitro-o-phenylenediamine is incompatible with strong oxidizing agents, strong acids, strong reducing agents, acid chlorides and acid anhydrides.

Fire Hazard

Flash point data for 4-Nitro-o-phenylenediamine are not available; however, 4-Nitro-o-phenylenediamine is probably combustible.

Biochem/physiol Actions

4-Nitro-o-phenylenediamine is a direct-acting mutagen.

Safety Profile

Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NOx,.

Purification Methods

Crystallise the diamine from water. [Beilstein 13 IV 75.]

4-Nitro-o-phenylenediamine(99-56-9)Related Product Information

• 4-Nitroaniline
• 4-Bromo-1,2-benzenediamine
• 3,4-Difluoronitrobenzene
• 1,3-Diaminoguanidine monohydrochloride
• m-Phenylenediamine
• o-Phenylenediamine
• 4-Nitrophthalic acid
• 3,4-Diaminotoluene
• p-Phenylenediamine
• 4-Nitrophthalonitrile
• Glycine
• ALTRENOGEST
• N-Methylbenzene-1,2-diamine
• Betaine
• 4-Nitrophthalimide
• 4-Nitrophthalic anhydride
• Nitrobenzene
• NITROGEN DIOXIDE