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m-Phenylenediamine

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m-Phenylenediamine Basic information

Product Name:
m-Phenylenediamine
Synonyms:
  • diaminobenzene
  • 1,3-Benzenediamine(9CI)
  • META PHENYLENE DIAMINE - FLAKE
  • benzenediamine
  • 1,3-Phenylenediamine CAS
  • meta-Phenylenediamine (MPD)
  • 1,3-DIAMINOBENZENE 99.5%
  • meta-aminoaniline
CAS:
108-45-2
MF:
C6H8N2
MW:
108.14
EINECS:
203-584-7
Product Categories:
  • Building Blocks
  • Chemical Synthesis
  • Nitrogen Compounds
  • Organic Building Blocks
  • Polyamines
  • Indazoles
  • Fine Chemicals
  • Organics
  • 1,3-Benzenediamine
  • Amines
  • Fluorenes, etc. (reagent for high-performance polymer research)
  • Functional Materials
  • Reagent for High-Performance Polymer Research
  • VARIOUSAMINE
  • Intermediates of Dyes and Pigments
Mol File:
108-45-2.mol
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m-Phenylenediamine Chemical Properties

Melting point:
64-66 °C(lit.)
Boiling point:
282-284 °C(lit.)
Density 
1,139 g/cm3
vapor density 
3.7 (vs air)
vapor pressure 
0.62 mm Hg ( 100 °C)
refractive index 
1.6339
Flash point:
>230 °F
storage temp. 
Store below +30°C.
solubility 
350g/l
pka
5.11, 2.50(at 20℃)
form 
pellets
color 
Yellow to light tan or brown gray
PH
8 (100g/l, H2O, 20℃)
Water Solubility 
350 g/L (25 ºC)
Sensitive 
Air Sensitive
Merck 
14,7283
BRN 
471357
InChIKey
WZCQRUWWHSTZEM-UHFFFAOYSA-N
CAS DataBase Reference
108-45-2(CAS DataBase Reference)
IARC
3 (Vol. 16, Sup 7) 1987
NIST Chemistry Reference
1,3-Benzenediamine(108-45-2)
EPA Substance Registry System
1,3-Phenylenediamine (108-45-2)
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Safety Information

Hazard Codes 
T,N
Risk Statements 
23/24/25-36-43-50/53-68-40
Safety Statements 
28-36/37-45-60-61-28A
RIDADR 
UN 1673 6.1/PG 3
WGK Germany 
2
RTECS 
SS7700000
8-10-23
Autoignition Temperature
560 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29215119
Hazardous Substances Data
108-45-2(Hazardous Substances Data)
Toxicity
LD50 in rats (mg/kg): 650 orally; 283 i.p. (Burnett)

MSDS

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m-Phenylenediamine Usage And Synthesis

Chemical Properties

Grey crystal granule

Chemical Properties

m-Phenylenediamine is a colorless to white crystalline substance that turns red upon exposure to air

Uses

1,3-Phenylenediamine is used in the foaming-type hair dye composition.

Uses

The appearance of the high purity of the m-phenylenediamine is snow white flake solid used as a synthetic electronic grade polyimide material and epoxy resin curing agent.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 6182, 1980 DOI: 10.1021/ja00539a054
The Journal of Organic Chemistry, 37, p. 930, 1972 DOI: 10.1021/jo00972a002

General Description

Colorless or white colored needles that turn red or purple in air. Melting point 64-66 C. Density 1.14 g / cm3. Flash point 280 F. May irritate skin and eyes. Toxic by skin absorption, inhalation or ingestion. Used in aramid fiber manufacture, as a polymer additive, dye manufacturing, as a laboratory reagent, and in photography.

Air & Water Reactions

Soluble in water [Merck].

Reactivity Profile

m-Phenylenediamine an aromatic amine, neutralizes acids, acid chlorides, acid anhydrides and chloroformates in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Incompatible with oxidizing agents .

Fire Hazard

m-Phenylenediamine is combustible. Dust may form explosive mixtures in air

Safety Profile

Suspected carcinogen with experimental tumorigenic and teratogenic data. Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Mildly toxic by skin contact. Mutation data reported. Combustible when exposed to heat or flame. A hair dye ingredtent. When heated to decomposition it emits toxic fumes of NOx. See also other phenylenediamine entries and AMINES.

Potential Exposure

Used in making various dyes; as a curing agent for epoxy resin; rubber, textile fibers; urethanes, corrosion inhibitors; adhesives; in photographic and analytical procedures and processes.

Carcinogenicity

"Occupational exposure to m-PDA may occur through inhalation and dermal contact with this compound at workplace where m-PDA is produced or used. The general population may be exposed to m-PDA via dermal contact with consumer products containing this compound."An IARC Working Group concluded, on the basis of lack of human data and inadequate animal data, that m-PDA was not classifiable (Group 3) as to its carcinogenicity to humans.

Metabolic pathway

By the perfused rat liver, 1,3-diaminobenzene (MPD) is metabolized to three identified N-acetylated derivatives N-acetyl-1,3-diaminobenzene, N,N'- diacetyl-1,3-diaminobenzene, and N,N'-diacetyl-2,4- diaminophenol which are identical to the metabolites excreted in rat urine.

Shipping

UN1673 Phenylenediamines (o-, m-, p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Purify the diamine by distillation under a vacuum followed by recrystallisation from EtOH (rhombs) and if necessary redistillation. It should be protected from light; otherwise it darkens rapidly. [Neilson et al. J Chem Soc 371 1962, IR: Katritzky & Jones J Chem Soc 3674, 2058 1959, UV: Forbes & Leckie Can J Chem 36 1371 1958.] The hydrochloride has m 277-278o, and the bis-4-chlorobenzenesulfonyl derivative has m 220-221o from H2O (214-215o, from MeOH/H2O) [Runge & Pfeiffer Chem Ber 90 1737 1957]. The acetate has m 191o. [Beilstein 13 IV 79.]

Incompatibilities

Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid chlorides; acid anhydrides; chloroformates. Heat and light contribute to instability. Keep away from metals.

Waste Disposal

Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalytic or thermal device.

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