P-Phenylenediamine

p-Phenylenediamine
Names
Preferred IUPAC name
Benzene-1,4-diamine
Other names
Paraphenylenediamine
1,4-Diaminobenzene
1,4-Phenylenediamine
Identifiers
3D model (JSmol)
749029
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.096 Edit this at Wikidata
EC Number
  • 203-404-7
KEGG
RTECS number
  • SS8050000
UNII
UN number 1673
  • InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2 ☒N
    Key: CBCKQZAAMUWICA-UHFFFAOYSA-N ☒N
  • InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
    Key: CBCKQZAAMUWICA-UHFFFAOYAD
  • Nc1ccc(N)cc1
Properties
C6H8N2
Molar mass 108.144 g·mol−1
Appearance White crystalline solid, darkens upon exposure to air[1]
Melting point 145 to 147 °C (293 to 297 °F; 418 to 420 K)[1]
Boiling point 267 °C (513 °F; 540 K)[1]
10% at 40°C, 87% at 107 C, 100% at 140 C [2]
Vapor pressure <1 mmHg (20°C)[3]
Acidity (pKa)
  • 2.97 (doubly protonated form; 20 °C, H2O)
  • 6.31 (conjugate acid; 20 °C, H2O)[4]
-70.28·10−6 cm3/mol
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H301, H311, H317, H319, H331, H410
P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
[6]
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
0
0
Flash point 156 °C; 312 °F; 429 K[3]
400 °C (752 °F; 673 K)
Lethal dose or concentration (LD, LC):
80 mg/kg (rat, oral)
98 mg/kg (rat, oral)
145 mg/kg (guinea pig, oral)[5]
250 mg/kg (rabbit, oral)
100 mg/kg (cat, oral)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.1 mg/m3 [skin][3]
REL (Recommended)
 TWA 0.1 mg/m3 [skin][3]
IDLH (Immediate danger)
 25 mg/m3[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation.[1] It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.

  1. ^ a b c d Merck Index, 11th Edition, 7256
  2. ^ "P-Phenylenediamine (1,4-Diaminobenzene)". Archived from the original on 2012-03-13. Retrieved 2011-07-14.
  3. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0495". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
  5. ^ a b "p-Phenylene diamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. ^ "p-Phenylenediamine MSDS". Thermo Fisher Scientific.