4,4'-Methylenedianiline

4,4'-Methylenedianiline
IUPAC name Bis(4-aminophenyl)methane
Other names 4,4'-Diaminodiphenylmethane; 4,4'-Methylenebisbenzenamine; MDA
Identifiers
CAS number	101-77-9 Y
PubChem	7577
UNII	GG5LL7OBZC Y
EC number	202-974-4
KEGG	C14288 N
ChEMBL	CHEMBL85728 N
RTECS number	BY5425000
Jmol-3D images	Image 1
SMILES c1cc(N)ccc1Cc2ccc(N)cc2
InChI 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
Properties
Molecular formula	C13H14N2
Molar mass	198.26 g mol−1
Density	1.05 g/cm3 (100°C)
Melting point	89 °C, 362 K, 192 °F
Boiling point	398-399 °C, 671-672 K, 748-750 °F
Solubility in water	0.125 g/100 ml (20 °C)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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. ^ ^{a b} ToxFAQs for 4,4'-Methylenedianiline, Agency for Toxic Substances and Disease Registry
2. ^ ^{a b} Background document for 4,4’-Diaminodiphenylmethane (MDA)[1]
3. ^ The Epping jaundice outbreak: a 24 year follow up.[2]
4. ^ ^{a b} Data on manufacture, import, export, uses and release of 4-4’ diaminodiphenylmethane as well as ... [3]

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

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Aromatic compound stubs Anilines IARC Group 2B carcinogens Wikimedia Foundation. 2010. Игры ⚽ Нужно сделать НИР? Methylene green MDAT Look at other dictionaries: MDA — may refer to: Contents 1 Companies, organizations and government bodies 2 Computing and technology 3 Game design 4 Publications …   Wikipedia National Emissions Standards for Hazardous Air Pollutants — The National Emissions Standards for Hazardous Air Pollutants (NESHAPs) are emissions standards set by the United States EPA for an air pollutant not covered by NAAQS that may cause an increase in fatalities or in serious, irreversible, or… …   Wikipedia List of IARC Group 2B carcinogens — Substances, mixtures and exposure circumstances in this list have been classified by the IARC as Group 2B: The agent (mixture) is possibly carcinogenic to humans. The exposure circumstance entails exposures that are possibly carcinogenic to… …   Wikipedia amine — aminic /euh mee nik, euh min ik/, adj. aminity /euh min i tee/, n. /euh meen , am in/, n. Chem. any of a class of compounds derived from ammonia by replacement of one or more hydrogen atoms with organic groups. [1860 65; AM(MONIUM) + INE2] * * *… …   Universalium 4,4'-diaminodiphénylméthane — Général Nom IUPAC 4,4 diaminodiphénylméthane Synonymes …   Wikipédia en Français MDA — Model Driven Architecture (Computing » Telecom) *** Muscular Dystrophy Association (Medical » Human Genome) ** Muscular Dystrophy Association (Community » Non Profit Organizations) * Media Development Authority (Computing » Software) * Mail… …   Abbreviations dictionary SMDA — Safe Medical Devices Act [of 1990]; starch methylenedianiline …   Medical dictionary SMDA — • Safe Medical Devices Act [of 1990]; • starch methylenedianiline …   Dictionary of medical acronyms & abbreviations 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”