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Merck
CN

31640

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:
101-77-9
Molecular Weight:
198.26
MDL number:
MFCD00007914
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329753859
EC Number:
202-974-4
Beilstein/REAXYS Number:
474706

Key Documents

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Product Name

4,4′-Diaminodiphenylmethane, analytical standard

InChI key

YBRVSVVVWCFQMG-UHFFFAOYSA-N

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

SMILES string

Nc1ccc(Cc2ccc(N)cc2)cc1

grade

analytical standard

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

Quality Level

100

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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.

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.
This compound is listed in the SVHC (Substances of very high concern) candidate list of ECHA (European Chemicals Agency)

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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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9922
BCCH2747
BCCB0422
BCBS5819V

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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)
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)
Hexamethylene diisocyanate, 2, 4?toluene diisocyanate, 2, 6?toluene diisocyanate, isophorone diisocyanate and 4, 4??methylene diphenyl diisocyanate?Determination of hexamethylenediamine, 2, 4?toluenediamine, 2, 6?toluenediamine, isophoronediamine and 4, 4??methylenedianiline in urine using gas chromatography?mass spectrometry [Biomonitoring Methods, 2017]
The MAK?Collection for Occupational Health and Safety: Annual Thresholds and Classifications for the Workplace, 2(3), 1415-1435 (2002)
4, 4'-Diaminodiphenylmethane.
Gooch, Jan W.
Encyclopedic Dictionary of Polymers, 204-205 (2011)
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