NP-MRD: Showing NP-Card for 4,4'-Methylenedianiline (NP0001320)

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Record Information

Version

2.0

Created at

2012-09-13 11:40:16 UTC

Updated at

2024-09-03 04:21:52 UTC

NP-MRD ID

NP0001320

Natural Product DOI

https://doi.org/10.57994/2649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4'-Methylenedianiline

Description

4,4'-Methylenedianiline belongs to the family of Diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups[1].

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305261923592D          

 15 16  0  0  0  0            999 V2000
    0.0000    2.4750    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=CC=C(CC2=CC=C(N)C=C2)C=C1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
YBRVSVVVWCFQMG-UHFFFAOYSA-N

> <FORMULA>
C13H14N2

> <MOLECULAR_WEIGHT>
198.2637

> <EXACT_MASS>
198.115698458

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.480621576245372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(4-aminophenyl)methyl]aniline

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.4071879349999996

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.8256718832674315

> <JCHEM_POLAR_SURFACE_AREA>
52.04

> <JCHEM_REFRACTIVITY>
65.19600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4'-diaminodiphenylmethane

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
CONECT    1    5   10                                                       
CONECT    2    6   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    1   12                                                       
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    4   13                                                       
CONECT    9   10   11                                                       
CONECT   10    1    2    9                                                  
CONECT   11    3    4    9                                                  
CONECT   12    5    6   14                                                  
CONECT   13    7    8   15                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Diphenylmethanediamine	ChEBI
4,4'-Methylenebis(benzeneamine)	ChEBI
4-(4-Aminobenzyl)aniline	ChEBI
alpha-(p-Aminophenyl)-p-toluidine	ChEBI
Bis(4-aminophenyl)methane	ChEBI
Bis(p-aminophenyl)methane	ChEBI
Bis-p-aminophenylmethane	ChEBI
DADPM	ChEBI
DAPM	ChEBI
DDM	ChEBI
Di-(4-aminophenyl)methane	ChEBI
Di-(p-aminophenyl)methane	ChEBI
Dianilinomethane	ChEBI
p,P'-diaminodiphenylmethane	ChEBI
p,P'-methylenedianiline	ChEBI
4,4'-Diaminodiphenylmethane	Kegg
a-(p-Aminophenyl)-p-toluidine	Generator
Α-(p-aminophenyl)-p-toluidine	Generator
4, 4'-Diphenylmethanediamine	HMDB
4, 4'-Methylenebis(aniline)	HMDB
4,4'-Diaminodiphenylmethan	HMDB
4,4'-Methylene(bisaniline)	HMDB
4,4'-Methylene-dianiline	HMDB
4,4'-Methylenebis-benzenamine	HMDB
4,4'-Methylenebis[aniline]	HMDB
4,4'-Methylenedi-aniline	HMDB
4,4'-Methylenedibenzenamine	HMDB
4,4-Methylenedianiline	HMDB
4-(4-Aminobenzyl)phenylamine (acd/name 4.0)	HMDB
Ancamine TL	HMDB
Araldite hardener 972	HMDB
Bis(aminophenyl)methane	HMDB
Bis-p-aminofenylmethan	HMDB
Curithane	HMDB
Di(4-aminophenyl)methane	HMDB
Diaminodiphenylmethane	HMDB
Dianilinemethane	HMDB
Epicure DDM	HMDB
Epikure DDM	HMDB
Jeffamine ap-20	HMDB
MDA	HMDB
Methylenebis(aniline)	HMDB
Methylenebis[aniline]	HMDB
Methylenedianiline	HMDB
p, P'-methylenedianiline	HMDB
p,P'-diaminodifenylmethan	HMDB
Sumicure m	HMDB
Tonox	HMDB
4,4'-Diaminodiphenylmethane, sodium chloride (3:1)	HMDB
4,4'-Diaminodiphenylmethane dihydrochloride	HMDB
4,4'-Methylene dianiline	HMDB
4,4'-Methylenebisaniline	HMDB
4,4'-MDA	HMDB
4,4'-Methylenedianiline	ChEBI

Chemical Formula

C₁₃H₁₄N₂

Average Mass

198.2637 Da

Monoisotopic Mass

198.11570 Da

IUPAC Name

4-[(4-aminophenyl)methyl]aniline

Traditional Name

4,4'-diaminodiphenylmethane

CAS Registry Number

101-77-9

SMILES

NC1=CC=C(CC2=CC=C(N)C=C2)C=C1

InChI Identifier

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

InChI Key

YBRVSVVVWCFQMG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum
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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-24	View Spectrum

Species

Species of Origin

Not Available

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
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic amine (CHEBI:32506 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	92.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1 mg/mL at 25 °C	Not Available
LogP	1.59	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.061 g/L	ALOGPS
logP	2.04	ALOGPS
logP	2.41	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	4.83	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	65.2 m³·mol⁻¹	ChemAxon
Polarizability	22.48 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

HMDB0041808

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7296

KEGG Compound ID

C14288

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4,4'-Methylenedianiline

METLIN ID

Not Available

PubChem Compound

7577

PDB ID

Not Available

ChEBI ID

32506

Good Scents ID

Not Available

References

General References

Pludro G, Karlowski K, Mankowska M, Woggon H, Uhde WJ: [Toxicological and chemical studies of some epoxy resins and hardeners. I. Study of acute and subacute toxicity of phthalic acid anhydride, 4,4'diaminodiphenylmethane and epoxy resin Epilox EG-34]. Acta Pol Pharm. 1969;26(4):353-8. [PubMed:5349261 ]
Yasuda SK: Determination of 3,3'-dichloro-4,4'-diaminodiphenylmethane in air. J Chromatogr. 1975 Feb 12;104(2):283-90. [PubMed:1150762 ]
Manis MO, Braselton WE Jr: Structure elucidation and in vitro reactivity of the major metabolite of 4,4'-methylenebis(2-chloroaniline) (MBOCA) in canine urine. Fundam Appl Toxicol. 1984 Dec;4(6):1000-8. [PubMed:6549168 ]
Robert A, Ducos P, Francin JM, Marsan P: Biological monitoring of workers exposed to 4,4'-methylenediphenyl diisocyanate (MDI) in 19 French polyurethane industries. Int Arch Occup Environ Health. 2007 Apr;80(5):412-22. doi: 10.1007/s00420-006-0150-3. Epub 2006 Oct 24. [PubMed:17061110 ]
Lu Y, Wang H, Song P, Liu S: [Determination of seven aromatic amines in hair dyes by capillary electrophoresis coupled with field-amplified sample stacking]. Se Pu. 2011 Nov;29(11):1122-7. [PubMed:22393703 ]

Showing NP-Card for 4,4'-Methylenedianiline (NP0001320)

MOL for NP0001320 (4,4'-Methylenedianiline)

3D MOL for NP0001320 (4,4'-Methylenedianiline)

3D SDF for NP0001320 (4,4'-Methylenedianiline)

3D-SDF for NP0001320 (4,4'-Methylenedianiline)

PDB for NP0001320 (4,4'-Methylenedianiline)

3D PDB for NP0001320 (4,4'-Methylenedianiline)

SMILES for NP0001320 (4,4'-Methylenedianiline)

INCHI for NP0001320 (4,4'-Methylenedianiline)

Structure for NP0001320 (4,4'-Methylenedianiline)

3D Structure for NP0001320 (4,4'-Methylenedianiline)