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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:
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

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

429.8 °F - closed cup

Flash Point(C)

221 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH SVHC Candidate List

CAS No.

EU REACH Annex XVII (Restriction List)

CAS No.

EU REACH Annex XIV (Authorisation List)

CAS No.

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Six transition metal--organic materials with the ditopic 4, 4?-diaminodiphenylmethane ligand: Synthesis, structure characterization and luminescent properties
Chisca D, et al.
Polyhedron, 192, 114844-114844 (2020)
Bing Yu et al.
Journal of ethnopharmacology, 165, 173-179 (2015-02-25)
Fuzi [the lateral root of Aconitum carmichaeli Debx (Ranunculaceae)] is a well-known traditional medicinal herb used to treat chronic heart failure (CHF). Aconitine-type alkaloids are major alkaloids that are responsible for the pharmacological activity and toxicity of this herb.To investigate
Carcinogenic and chronic effects of 4,4'-diaminodiphenylmethane, an epoxyresin hardener.
R Schoental
Nature, 219(5159), 1162-1163 (1968-09-14)
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)
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