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Names | |
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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
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Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.002.705 |
EC Number |
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KEGG | |
PubChem
CID
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RTECS number |
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UNII | |
UN number | 2651 |
CompTox Dashboard (
EPA)
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Properties | |
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) |
0.125 g/100 ml (20 °C) | |
Vapor pressure | 0.0000002 mmHg (20°C) [1] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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potential carcinogen [1] |
GHS labelling: | |
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Danger | |
H317, H341, H350, H370, H373, H411 [2] | |
P201, P260, P273, P280, P308+P313 [2] | |
Flash point | 190 °C; 374 °F; 463 K [1] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 0.010 ppm ST 0.100 ppm [1] |
REL (Recommended)
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Ca [1] |
IDLH (Immediate danger)
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Ca [N.D.] [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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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.
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 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. [9]
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. [10]