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 MDA dadpm 4,4′-Diaminodiphenylmethane 4,4′-Methylenebisbenzenamine para,para′-Diaminodiphenylmethane Dianilinomethane 4,4′-Diphenylmethanediamine Bis(4-aminophenyl)methane
Identifiers
CAS Number	101-77-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:32506 N
ChEMBL	ChEMBL85728 N
ChemSpider	7296 N
ECHA InfoCard	100.002.705
EC Number	202-974-4
KEGG	C14288 N
PubChem CID	7577
RTECS number	BY5425000
UNII	GG5LL7OBZC Y
UN number	2651
CompTox Dashboard (EPA)	DTXSID6022422
InChI 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
Chemical formula	C13H14N2
Molar mass	198.269 g·mol−1
Appearance	Colorless solid
Odor	faint, amine-like[1]
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)
Solubility in water	0.125 g/100 ml (20 °C)
Vapor pressure	0.0000002 mmHg (20°C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	potential carcinogen[1]
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H317, H341, H350, H370, H373, H411[2]
Precautionary statements	P201, P260, P273, P280, P308+P313[2]
Flash point	190 °C; 374 °F; 463 K[1]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.010 ppm ST 0.100 ppm[1]
REL (Recommended)	Ca[1]
IDLH (Immediate danger)	Ca [N.D.][1]
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

Synthesis and applications

In the industrial production, MDA is produced by reaction of formaldehyde and aniline in the presence of hydrochloric acid.^[3]

MDA is a common monomer in the synthesis of polymer materials. These include polyamides,^[4] polyimides and polyimines.^[5] MDA is also used extensively as a precursor to methylene diphenyl diisocyanate (MDI). Here, MDA is treated with phosgene to produce MDI. MDI, in turn, is a precursor to many polyurethane foams.^[6][7] Lower quantities are used as hardeners in epoxy resins and adhesives, as well as in the production of high-performance polymers.^[3] Additionally, hydrogenation of MDA can be performed to produce 4,4,diaminodicyclohexylmethane, which is also used in polymer chemistry.^[8]

MDA can also be applied as a bidentate (bridging) ligand in the formation of metal-coordination complexes.^[9]

Safety

MDA is considered a potential occupational carcinogen by the US National Institute for Occupational Safety and Health. The Occupational Safety and Health Administration has set a permissible exposure limit at 0.01 ppm over an eight-hour time-weighted average, and a short-term exposure limit at 0.1 ppm.^[10]

It is suspected carcinogen.^[6] It is included in the "substances of very high concern" list of the European Chemicals Agency (ECHA).^[7] The compound was blamed in a mass poisoning in the vicinity of Epping, Essex, United Kingdom during 1965 during which 84 individuals were poisoned through accidental contamination of flour used to make bread.^[11]

Related compounds

• 4,4'-Thiodianiline
• 4,4'-Oxydianiline
• Dapsone