4,4'-Methylenedianiline

4,4′-Methylenedianiline (MDA) is an organic compound with the formula CH2(C6H4NH2)2. It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes.

4,4′-Methylenedianiline
Names
Preferred IUPAC name
4,4′-Methylenedianiline
Other names
4,4′-Diaminodiphenylmethane; 4,4′-Methylenebisbenzenamine; MDA; para,para′-Diaminodiphenylmethane; Dianilinomethane; 4,4′-Diphenylmethanediamine; Bis(4-aminophenyl)methane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.705
EC Number
  • 202-974-4
KEGG
PubChem CID
RTECS number
  • BY5425000
UNII
UN number 2651
  • InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2 N
    Key: YBRVSVVVWCFQMG-UHFFFAOYSA-N N
  • InChI=1/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2
    Key: YBRVSVVVWCFQMG-UHFFFAOYAE
SMILES
  • c1cc(N)ccc1Cc2ccc(N)cc2
Properties
C13H14N2
Molar mass 198.269 g·mol−1
Appearance Colorless solid
Odor faint, amine-like
Density 1.05 g/cm3 (100°C)
Melting point 89 °C (192 °F; 362 K)
Boiling point 398 to 399 °C (748 to 750 °F; 671 to 672 K)
0.125 g/100 ml (20 °C)
Vapor pressure 0.0000002 mmHg (20°C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 potential carcinogen
GHS labelling:
Danger
H317, H341, H350, H370, H373, H411
P201, P260, P273, P280, P308+P313
Flash point 190 °C; 374 °F; 463 K
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.010 ppm ST 0.100 ppm
REL (Recommended)
 Ca
IDLH (Immediate danger)
 Ca [N.D.]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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