4,4'-Methylenedianiline

4,4'-Methylenedianiline
Names
	IUPAC name Bis(4-aminophenyl)methane
	Other names 4,4'-Diaminodiphenylmethane; 4,4'-Methylenebisbenzenamine; MDA; para, para'-Diaminodiphenyl-methane; Dianilinomethane; 4,4'-Diphenylmethanediamine
Identifiers
CAS Number	101-77-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32506 ;
ChemSpider	7296 ;
ECHA InfoCard	100.002.705
EC Number	202-974-4
KEGG	C14288 ;
PubChem CID	7577;
RTECS number	BY5425000
UNII	GG5LL7OBZC ;
UN number	2651
	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 Key: YBRVSVVVWCFQMG-UHFFFAOYSA-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	198.27 g·mol−1
Appearance	Pale brown, crystalline 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)
Solubility in water	0.125 g/100 ml (20 °C)
Vapor pressure	0.0000002 mmHg (20°C)
Hazards
Main hazards	potential carcinogen
Flash point	190 °C; 374 °F; 463 K
	US health exposure limits (NIOSH):
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).
	verify (what is ?)
	Infobox references

4,4'-Methylenedianiline (MDA) is an organic compound]] with the formula CH₂(C₆H₄NH₂)₂. It is a colorless or white solid. It is produced on industrial scale as a precursor to polyurethanes.

Synthesis and applications

In the industrial production, MDA is produced by reaction of formaldehyde and aniline in the presence of hydrochloric acid.^[2] This reaction consumes the majority of aniline produced worldwide.^[3]

MDA is consumed mainly as a precursor to 4,4 ́-methylene diphenyl diisocyanate (MDI). MDA is treated with phosgene to give MDI. MDI is a precursor to many polyurethane foams.^[4]^[5] Lower quantities are used as hardeners in epoxy resins and adhesives, as well as in the production of high-performance polymers.^[2] MDA is hydrogenated to give 4,4-diaminodicyclohexylmethane, which is also used in polymer chemistry.

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 0.10 ppm.^[6]

It is suspected carcinogen.^[4] It is included in the "substances of very high concern" list of the European Chemicals Agency (ECHA).^[5] The compound was blamed in an 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.^[7]

^ ^a ^b ^c ^d ^e ^f ^g "NIOSH Pocket Guide to Chemical Hazards #0415". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b Data on manufacture, import, export, uses and release of 4-4’ diaminodiphenylmethane as well as ... [1]
^ Christian Six, Frank Richter "Isocyanates, Organic" in Ulmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a14_611
^ ^a ^b ToxFAQs for 4,4'-Methylenedianiline, Agency for Toxic Substances and Disease Registry
^ ^a ^b Background document for 4,4’-Diaminodiphenylmethane (MDA)
^ [2] NIOSH Pocket Guide on Chemical Hazards
^ Kopelman, H; Robertson, MH; Sanders, PG; Ash, I. "The Epping jaundice". Br Med J. 1: 514–6. PMC 1843808 . PMID 5902696.

International Labour Organization icsc1111
Centers for Disease Control and Prevention NIOSH Pocket Guide to Chemical Hazards
European Union Risk Assessment Report
J.H. Petersen, S.K. Mortensen, G.A. Pedersen, Memorandum for the Danish Veterinary and Food Administration on An acute case of primary aromatic amines migrating from cooking utensils^{[permanent dead link]}, Danish Institute for Food and Veterinary Research, 12 October 2004

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f ^g "NIOSH Pocket Guide to Chemical Hazards #0415". National Institute for Occupational Safety and Health (NIOSH).

[industr_prodn-2] Data on manufacture, import, export, uses and release of 4-4’ diaminodiphenylmethane as well as ... [1]

[Ullmann-3] Christian Six, Frank Richter "Isocyanates, Organic" in Ulmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a14_611

[atsdr-4] ToxFAQs for 4,4'-Methylenedianiline, Agency for Toxic Substances and Disease Registry

[ECHA-5] Background document for 4,4’-Diaminodiphenylmethane (MDA)

[pocket-6] [2] NIOSH Pocket Guide on Chemical Hazards

[NCBI-7] Kopelman, H; Robertson, MH; Sanders, PG; Ash, I. "The Epping jaundice". Br Med J. 1: 514–6. PMC 1843808 . PMID 5902696.

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