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66681

Supelco

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
Beilstein/REAXYS Number:
1882318
EC Number:
202-918-9
MDL number:
MFCD00047829
UNSPSC Code:
41116107
PubChem Substance ID:
329760302
NACRES:
NA.24

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

SMILES string

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

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

InChI key

IBOFVQJTBBUKMU-UHFFFAOYSA-N

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General description

4,4′-Methylene-bis(2-chloroaniline) is an azo dye metabolite that is deemed toxic to the environment.

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

Standard for determining aromatic amines released from azo-dyes in commodities

Recommended products

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.

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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_germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0003
BCCF0864
BCCD2377
BCBZ8345
BCBX4018

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Degradability of selected azo dye metabolites in activated sludge systems.
Ekici P, et al.
Chemosphere, 44(4), 721-728 (2001)
G. Rohm et al.
GIT Labor-Fachzeit., 1080-1080 (1997)
Wei-Chung Shih et al.
Rapid communications in mass spectrometry : RCM, 21(24), 4073-4078 (2007-11-17)
Analysis of 4,4'-methylenebis(2-cholroaniline) (MOCA) or its metabolites in urine has been considered as the appropriate method to assess MOCA exposures through inhalation and skin absorption. MOCA and its metabolite, N-acetyl 4,4'-methylenebis(2-chloroaniline) (acetyl-MOCA), are analyzed using methods either limited by sensitivity
L Luukkanen et al.
Pharmacology & toxicology, 80(3), 152-158 (1997-03-01)
Rats were treated with acetone, pyrazole, phenobarbital, 4,4'-methylenebis-(2-chloroaniline) (MOCA), 3-methylcholanthrene, creosote oil, or a mixture of polychlorinated biphenyls (Aroclor 1254) to study the inducibility and enzyme kinetics of UDP-glucuronosyltransferases towards 1-hydroxypyrene, which is a human metabolite and a urinary biomarker
Hong-I Chen et al.
Journal of occupational health, 49(5), 389-398 (2007-10-24)
Oxidative DNA damage may play an important role in the human carcinogenic process. Recently, we reported a case of bladder cancer among 4, 4'-methylenebis (2-chloroaniline) (MBOCA)-exposed workers. By measuring the plasma level of 8-hydroxydeoxyguanosine (8-OHdG), we investigated the association between
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