Methylene Dianiline

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Methylene Dianiline
	File:4-4'-methylenedianiline.svg
Names
	IUPAC name Bis(4-aminophenyl)methane
	Other names 4,4'-Diaminodiphenylmethane; 4,4'-Methylenebisbenzenamine; MDA
Identifiers
CAS Number	101-77-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL85728 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG	C14288 ;
PubChem CID	7577;
UNII	GG5LL7OBZC ;
	InChI 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;
	SMILES c1cc(N)ccc1Cc2ccc(N)cc2;
Properties
Chemical formula	C13H14N2
Molar mass	198.27 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Template:Chembox ECNumber Template:Chembox E number Template:Chembox RTECS Template:Chembox Density Template:Chembox MeltingPt Template:Chembox SolubilityInWater

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [2]

Overview

4,4'-Methylenedianiline (MDA) is a suspected carcinogen.^[1] It is included in the "substances of very high concern" list of the European Chemicals Agency (ECHA).^[2] The compound was involved in an accidental 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.^[3]

Synthesis

In the industrial production, MDA is synthesised by reaction of formaldehyde and aniline in the presence of hydrochloric acid.^[4]

Uses

MDA is used primarily for making polyurethane foams in which case it is first reacted with phosgene to create 4,4 ́-methylene diphenyl diisocyanate (MDI) prior to polymerization with a polyol.^[1]^[2] Lower quantities are used as hardeners in epoxy resins and adhesives, as well as in the production of high-performance polymers.^[4]

References

↑ ^1.0 ^1.1 ToxFAQs for 4,4'-Methylenedianiline, Agency for Toxic Substances and Disease Registry
↑ ^2.0 ^2.1 Background document for 4,4’-Diaminodiphenylmethane (MDA)
↑ The Epping jaundice outbreak: a 24 year follow up
↑ ^4.0 ^4.1 Data on manufacture, import, export, uses and release of 4-4’ diaminodiphenylmethane as well as ... [1]

External links

International Labor Organisation icsc1111
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, Danish Institute for Food and Veterinary Research, 12 October 2004

cs:4,4'- Diaminodifenylmethan de:4,4′-Diaminodiphenylmethan fa:۴٬۴'-متیلن‌دی‌آنیلین nl:4,4'-methyleendianiline fi:4,4'-metyleenidianiliini

[atsdr-1] 1.0 ^1.1 ToxFAQs for 4,4'-Methylenedianiline, Agency for Toxic Substances and Disease Registry

[ECHA-2] 2.0 ^2.1 Background document for 4,4’-Diaminodiphenylmethane (MDA)

[NCBI-3] The Epping jaundice outbreak: a 24 year follow up

[industr_prodn-4] 4.0 ^4.1 Data on manufacture, import, export, uses and release of 4-4’ diaminodiphenylmethane as well as ... [1]

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