NP-MRD: Showing NP-Card for bis amine (NP0148089)

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Record Information

Version

2.0

Created at

2022-09-02 03:47:54 UTC

Updated at

2022-09-02 03:47:54 UTC

NP-MRD ID

NP0148089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bis amine

Description

4,4'-Methylenebis(2-chloroaniline), also known as MOCA, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 4,4'-Methylenebis(2-chloroaniline) is a strong basic compound (based on its pKa). 4,4'-Methylenebis(2-chloroaniline) (MBOCA) is a synthetic chemical used primarily to make polyurethane products. 4,4'-Methylenebis(2-chloroaniline) is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. The mainy enzymes involves are phenobarbital-inducible cytochrome P-450 enzymes. MBOCA and its metabolites are excreted mainly in the urine. Other N-oxidized MBOCA metabolites, such as n-hydroxy MBOCA and mononitroso-MBOCA, have been shown to form hemoglobin adducts. It may be found in gears, gaskets, sport boots, roller skate wheels, shoe soles, rolls and belt drives in cameras, computers and copy machines, wheels and pulleys for escalators and elevators, components in home appliances, and various military applications. Metabolism involves N-acetylation, N-hydroxylation (which may be followed by n-oxidation), and ring hydroxylation. It is also used as a coating in chemical reactions to set glues, plastics, and adhesives. 4,4'-Methylenebis(2-chloroaniline) is a known human carcinogen. bis amine is found in Apis cerana and Trypanosoma brucei. bis amine was first documented in 2009 (PMID: 19447850). One metabolite in particular, N-hydroxy-N,N’-diacetyl MBOCA, is known to bind nucleic acids, forming DNA adducts (PMID: 21501672).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204182D          

 17 18  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0148089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C13H12Cl2N2

> <MOLECULAR_WEIGHT>
267.154

> <EXACT_MASS>
266.037753808

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.738569721264057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
3.6152772876666663

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.0975125919051716

> <JCHEM_POLAR_SURFACE_AREA>
52.04

> <JCHEM_REFRACTIVITY>
74.80560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bis amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.334 -10.010   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7                                                       
CONECT   15    5   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Methylenebis(chloroaniline)	ChEBI
MOCA	ChEBI
3,3'-dichloro-4,4'-Diaminodiphenylmethane	MeSH
Methylene bis(chloroaniline)	MeSH
MBOCA	MeSH

Chemical Formula

C₁₃H₁₂Cl₂N₂

Average Mass

267.1540 Da

Monoisotopic Mass

266.03775 Da

IUPAC Name

4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline

Traditional Name

bis amine

CAS Registry Number

Not Available

SMILES

NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl

InChI Identifier

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aniline or substituted anilines
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

chloroaniline (CHEBI:28124 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.72	ALOGPS
logP	3.62	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.81 m³·mol⁻¹	ChemAxon
Polarizability	26.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C10999

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4,4'-Methylenebis(2-chloroaniline)

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28124

Good Scents ID

Not Available

References

General References

Cocker J, Cain JR, Baldwin P, McNally K, Jones K: A survey of occupational exposure to 4,4'-methylene-bis (2-chloroaniline) (MbOCA) in the UK. Ann Occup Hyg. 2009 Jul;53(5):499-507. doi: 10.1093/annhyg/mep026. Epub 2009 May 15. [PubMed:19447850 ]
Keen C, Coldwell M, McNally K, Baldwin P, McAlinden J, Cocker J: A follow up study of occupational exposure to 4,4'-methylene-bis(2-chloroaniline) (MbOCA) and isocyanates in polyurethane manufacture in the UK. Toxicol Lett. 2012 Aug 13;213(1):3-8. doi: 10.1016/j.toxlet.2011.04.003. Epub 2011 Apr 8. [PubMed:21501672 ]
LOTUS database [Link]

Showing NP-Card for bis amine (NP0148089)

MOL for NP0148089 (bis amine)

3D MOL for NP0148089 (bis amine)

3D SDF for NP0148089 (bis amine)

3D-SDF for NP0148089 (bis amine)

PDB for NP0148089 (bis amine)

3D PDB for NP0148089 (bis amine)

SMILES for NP0148089 (bis amine)

INCHI for NP0148089 (bis amine)

Structure for NP0148089 (bis amine)

3D Structure for NP0148089 (bis amine)