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Merck
CN

66681

4,4′-Methylene-bis(2-chloroaniline)

analytical standard

Synonym(s):

2,2′-Dichloro-4,4′-methylenedianiline, 4,4′-Diamino-3,3′-dichlorodiphenylmethane

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About This Item

Linear Formula:
CH2[C6H3(Cl)NH2]2
CAS Number:
101-14-4
Molecular Weight:
267.15
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329760302
EC Number:
202-918-9
Beilstein/REAXYS Number:
1882318
MDL number:
MFCD00047829

Key Documents

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SMILES string

Nc1ccc(Cc2ccc(N)c(Cl)c2)cc1Cl

InChI key

IBOFVQJTBBUKMU-UHFFFAOYSA-N

InChI

1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2

grade

analytical standard

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

bp

202-214 °C/0.3 mmHg (lit.)

mp

102-107 °C (lit.)

application(s)

environmental

format

neat

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General description

4,4′-Methylene-bis(2-chloroaniline) is an azo dye metabolite that is deemed toxic to the environment.
This compound is listed in the SVHC (Substances of very high concern) candidate list of ECHA (European Chemicals Agency)

Application

4,4′-Methylene-bis(2-chloroaniline) may be used as an analytical reference standard for the determination of 4,4′-methylene-bis(2-chloroaniline) in:
  • Urine samples by high performance liquid chromatography (HPLC).
  • Textile samples by HPLC coupled to tandem mass spectrometry (MS/MS) equipped with multiple reaction monitoring (MRM) mode of detection.
  • Plastic multilayer food packaging materials by LC-Orbitrap-full scan-high resolution mass spectrometry (HRMS) equipped with electrospray ionization (ESI) source.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
Standard for determining aromatic amines released from azo-dyes in commodities

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Muta. 2

Storage Class

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

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0003
BCCF0864
BCCD2377
BCBZ8345
BCBX4018

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G. Rohm et al.
GIT Labor-Fachzeit., 1080-1080 (1997)
Degradability of selected azo dye metabolites in activated sludge systems.
Ekici P, et al.
Chemosphere, 44(4), 721-728 (2001)
LC-MS/MS method for the confirmatory determination of aromatic amines and its application in textile analysis.
Sutthivaiyakit P, et al.
Analytical and Bioanalytical Chemistry, 381(1), 268-276 (2005)
Evaluation of worker exposure to TDI, MOCA, and methylene chloride.
Richard Fairfax et al.
Journal of occupational and environmental hygiene, 3(6), D50-D53 (2006-04-20)
P Vineis et al.
Cancer causes & control : CCC, 8(3), 346-355 (1997-05-01)
Epidemiological evidence on the relation between aromatic amines and cancer risk is reviewed. In particular, cancer risk in humans resulting from exposure to aromatic amines from occupational sources and tobacco smoking is assessed with reference to ecologic, cohort, and case-control
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