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Substance Name: Methylenebis(chloroaniline)
RN: 101-14-4
UNII: 3L2W5VTT2A
InChIKey: IBOFVQJTBBUKMU-UHFFFAOYSA-N

Note

  • Aromatic diamine used in the plastics industry as curing agent for epoxy resins and urethane rubbers. It causes bladder, liver, lung, and other neoplasms.

Molecular Formula

  • C13-H12-Cl2-N2

Molecular Weight

  • 267.158
 

Classification Codes

Classification Codes

  • Mutation Data
  • Tumor Data

Superlist Classification Codes

  • 2007 CERCLA Priority List, Rank: 152
  • 2011 CERCLA Priority List, Rank: 90
  • Carcinogenic to Humans (Group 1)
  • Overall Carcinogenic Evaluation: Group 1
  • Reasonably Anticipated to be a Carcinogen
  • Reportable Quantity (RQ) = 10 lb
  • TWA (0.01 ppm); skin; Suspected human carcinogen; BEI

Names and Synonyms

Results Name

  • Methylenebis(chloroaniline)

Name of Substance

  • 4,4'-Methylenebis(2-chloroaniline)
  • Methylenebis(chloroaniline)

MeSH Heading

  • Methylenebis(chloroaniline)

Synonyms

  • 1-13-00-00074 (Beilstein Handbook Reference)
  • 3,3'-Dichlor-4,4'-diaminodiphenylmethan
  • 3,3'-Dichlor-4,4'-diaminodiphenylmethan [German]
  • 3,3'-Dichloro-4,4'-diaminodifenilmetano
  • 3,3'-Dichloro-4,4'-diaminodifenilmetano [Italian]
  • 3,3'-Dichloro-4,4'-diaminodiphenylmethane
  • 3,3'-Dicloro-4,4'-diaminodifenilmetano
  • 3,3'-Dicloro-4,4'-diaminodifenilmetano [Italian]
  • 4,4'-Diamino-3,3'-dichlorodiphenylmethane
  • 4,4'-Methylene(bis)-chloroaniline
  • 4,4'-Methylenebis(2-chloroaniline)
  • 4,4'-Methylenebis(o-chloroaniline)
  • 4,4'-Methylenebis-2-chlorobenzenamine
  • 4,4-Metilene-bis-o-cloroanilina
  • 4,4-Metilene-bis-o-cloroanilina [Italian]
  • Aniline, 4,4'-methylenebis(2-chloro-
  • Benzenamine, 4,4'-methylenebis(2-chloro-
  • Bis amine
  • Bis(3-chloro-4-aminophenyl)methane
  • Bis(4-amino-3-chlorophenyl)methane
  • Bis-amine A
  • Bisamine
  • Bisamine S
  • BRN 1882318
  • CCRIS 389
  • CL-Mda
  • Cuamine M
  • Cuamine MT
  • Curalin M
  • Curene 442
  • Cyanaset
  • Dacpm
  • Di(-4-amino-3-chlorophenyl)methane
  • Di-(4-amino-3-clorofenil)metano
  • Di-(4-amino-3-clorofenil)metano [Italian]
  • Diamet Kh
  • EC 202-918-9
  • EINECS 202-918-9
  • HSDB 2629
  • LD 813
  • MBOCA
  • Methylene 4,4'-bis(o-chloroaniline)
  • Methylene-bis-orthochloroaniline
  • Methylenebis(3-chloro-4-aminobenzene)
  • Methylenebis(chloroaniline)
  • Millionate M
  • MOCA
  • MOCA (curing agent)
  • NSC 52954
  • p,p'-Methylenebis(alpha-chloroaniline)
  • p,p'-Methylenebis(o-chloroaniline)
  • p,p'-Methylenebis(ortho-chloroaniline)
  • Quodorole
  • RCRA waste number U158
  • UNII-3L2W5VTT2A

Systematic Names

  • 4,4'-Methylenebis(2-chloroaniline)
  • Aniline, 4,4'-methylenebis(2-chloro- (8CI)
  • Benzenamine, 4,4'-methylenebis(2-chloro-

Superlist Names

  • 4,4'-Methylene bis(2-chloroaniline)
  • 4,4'-Methylenebis(2-chloroaniline)
  • Aniline, 4,4'-methylenebis(2-chloro-
  • Benzenamine, 4,4'-methylenebis(2-chloro-
  • MBOCA
  • MOCA
  • RCRA waste no. U158

Registry Numbers

CAS Registry Number

  • 101-14-4

FDA UNII

  • 3L2W5VTT2A

Other Registry Numbers

  • 126699-69-2
  • 142661-36-7
  • 1899048-27-1
  • 1951406-44-2
  • 29371-14-0
  • 51065-07-7
  • 78642-65-6
  • 913092-91-8

System Generated Number

  • 0000101144

Structure Descriptors

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

InChIKey

IBOFVQJTBBUKMU-UHFFFAOYSA-N

Smiles

c1(c(ccc(c1)Cc1cc(c(N)cc1)Cl)N)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 400mg/kg (400mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: ATAXIA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(6), Pg. 86, 1990.
mouse LD50 intraperitoneal 64mg/kg (64mg/kg)   Progress in Mutation Research. Vol. 1, Pg. 682, 1981.
mouse LD50 oral 640mg/kg (640mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(6), Pg. 86, 1990.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 6, Pg. 988, 1991.
rat LD50 oral 1140mg/kg (1140mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: ATAXIA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(6), Pg. 86, 1990.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Naturwissenschaften. Vol. 58, Pg. 578, 1971.
rat LDLo unreported 1gm/kg (1000mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
American Industrial Hygiene Association Journal. Vol. 32, Pg. 802, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 110 deg C   EXP
Boiling Point 378.9 deg C   EXP
log P (octanol-water) 3.91 (none)   EXP
Water Solubility 13.9 mg/L 24 EXP
Vapor Pressure 2.86E-07 mm Hg 25 EST
Henry's Law Constant 4.06E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.75E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.