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Sigma-Aldrich

4,4′-Diaminodiphenylmethane

≥97.0% (GC)

Synonym(s):

4,4′-Methylenedianiline, MDA

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About This Item

Empirical Formula (Hill Notation):
C13H14N2
CAS Number:
101-77-9
Molecular Weight:
198.26
Beilstein/REAXYS Number:
474706
EC Number:
202-974-4
MDL number:
MFCD00007914
UNSPSC Code:
12352100
PubChem Substance ID:
57648737
NACRES:
NA.22

assay

≥97.0% (GC)

mp

88-92 °C

solubility

water: soluble

SMILES string

Nc1ccc(Cc2ccc(N)cc2)cc1

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

InChI key

YBRVSVVVWCFQMG-UHFFFAOYSA-N

Gene Information

mouse ... Slc6a2(20538)
rat ... Slc6a3(24898) , Slc6a4(25553)

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General description

4,4′-diaminodiphenylmethane acts as a bidentate-bridging ligand, forming hydrogen bonds with its amine hydrogen atoms, and also participates in several non-covalent interactions.

application

4,4′-Diaminodiphenylmethane was employed:
  • as dummy template for bisphenols imprinting
  • in the synthesis of amino modified multi-walled carbon nanotubes/polydimethylsiloxane
  • as curing agent to study the kinetics of formation of epoxy resin composites
  • in rubber industry as an epoxyresin hardener

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 2 - Carc. 1B - Muta. 2 - Skin Sens. 1 - STOT RE 2 - STOT SE 1

target_organs

Liver, Liver,eye - retina

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

429.8 °F - closed cup

flash_point_c

221 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Carcinogenic and chronic effects of 4,4'-diaminodiphenylmethane, an epoxyresin hardener.
R Schoental
Nature, 219(5159), 1162-1163 (1968-09-14)
Jessica M Labonté et al.
The ISME journal, 9(11), 2386-2399 (2015-04-08)
Viral infections dynamically alter the composition and metabolic potential of marine microbial communities and the evolutionary trajectories of host populations with resulting feedback on biogeochemical cycles. It is quite possible that all microbial populations in the ocean are impacted by
Cong Hu et al.
Journal of chromatography. A, 1300, 165-172 (2013-06-04)
In this work, amino modified multi-walled carbon nanotubes/polydimethylsiloxane (multi-walled carbon nanotubes-4,4'-diaminodiphenylmethane/polydimethylsiloxane, MWCNTs-DDM/PDMS) was synthesized, and utilized as a novel coating for stir bar sorptive extraction (SBSE) of seven phenols (phenol, 2-chlorophenol, 2-nitrophenol, 4-nitrophenol, 2,4-dimethylphenol, p-choro-m-cresol and 2,4,6-trichlorphenol) in environmental water
A dsc kinetic study on the effect of filler concentration on crosslinking of diglycidylether of bisphenol-A with 4, 4'-diaminodiphenylmethane.
de Miranda MIG, et al.
Polymer, 38(5), 1017-1020 (1997)
Xiaoli Sun et al.
Journal of chromatography. A, 1343, 33-41 (2014-04-15)
A simple and fast method for both dummy template selection and polymer composition optimization is proposed here. A series of dummy templates for bisphenols imprinting were screened by running them on a non-imprinted polymer (NIP) column with porogen solvent as
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