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4,4′-Diaminodiphenylmethane

analytical standard

Synonym(s):

DAPM, 4,4′-Methylenedianiline, MDA

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About This Item

Empirical Formula (Hill Notation):
C13H14N2
CAS Number:
Molecular Weight:
198.26
Beilstein/REAXYS Number:
474706
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

analytical standard

Quality Level

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

88-92 °C

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

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

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General description

4,4′-Diaminodiphenylmethane (MDA) is an aromatic diamine, which finds industrial applications as a precursor in the manufacturing of polyurethane products, isocyanates, polyisocyanates, etc. It is also used as a hardener in the production of epoxy resins and elastomers.
4,4′-Diaminodiphenylmethane is a curing agent for epoxy resins. It is prepared from formaldehyde aniline when heated with aniline hydrochloride and aniline.

Application

4,4′-Diaminodiphenylmethane is used as an analytical reference standard for the quantification of the analyte in the following:
  • Urine samples using gas-chromatography coupled to mass spectrometry (GC-MS).
  • Hepatic microsomal incubation mixture from rabbits using high-performance liquid chromatography-plasma spray mass spectrometry (HPLC-PSP-MS), offline HPLC with fast atom bombardment mass spectrometry (FAB-MS) and fast atom bombardment tandem mass spectrometry (FAB-MS/MS).

It is reported to be used in the synthesis of amino modified multi-walled carbon nanotubes/polydimethylsiloxane, which serves as a coating for the stir bar sorptive extraction (SBSE) of phenols in environmental samples, followed by analysis using high performance liquid chromatography with ultraviolet detection (HPLC-UV).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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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

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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4, 4'-Diaminodiphenylmethane.
Gooch, Jan W.
Encyclopedic Dictionary of Polymers, 204-205 (2011)
Amino modified multi-walled carbon nanotubes/polydimethylsiloxane coated stir bar sorptive extraction coupled to high performance liquid chromatography-ultraviolet detection for the determination of phenols in environmental samples
Journal of Chromatography A, 1300(42), 165-172 (2013)
Characterization of biliary conjugates of 4, 4?-methylenedianiline in male versus female rats
Toxicology and Applied Pharmacology, 232(2), 190-202 (2008)
Identification of metabolites of 4, 4'-diaminodiphenylmethane (methylene dianiline) using liquid chromatographic and mass spectrometric techniques
Journal of Chromatography. B, Biomedical Sciences and Applications, 583(1), 63-76 (1992)
Malin Frick-Engfeldt et al.
Contact dermatitis, 57(3), 138-151 (2007-08-08)
We have previously shown that patch test preparations of polymeric diphenylmethane diisocyanate (PMDI) are more stable than preparations of diphenylmethane-4,4'-diisocyanate (4,4'-MDI). This study was conducted to (i) investigate whether PMDIs yield as many positive reactions as 4,4'-MDI, (ii) study concurrent

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