You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:50:30 UTC
Update Date2019-07-23 06:11:16 UTC
HMDB IDHMDB0032562
Secondary Accession Numbers
  • HMDB32562
Metabolite Identification
Common NameDiphenylamine
DescriptionDiphenylamine, also known as anilinobenzene or C6H5-NH-C6H5, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Diphenylamine is found, on average, in the highest concentration within garden onions (Allium cepa). Diphenylamine has also been detected, but not quantified in, several different foods, such as corianders (Coriandrum sativum), red tea, lemons (Citrus limon), teas (Camellia sinensis), and herbal tea. This could make diphenylamine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Diphenylamine.
Structure
Data?1563862276
Synonyms
ValueSource
(Phenylamino)benzeneChEBI
AnilinobenzeneChEBI
C6H5-NH-C6H5ChEBI
DPAChEBI
N,N-DiphenylamineChEBI
N-PhenylbenzenamineChEBI
(phenylamino)-BenzeneHMDB
2-Biphenylyl-N-pyridyl-acetamideHMDB
2-Biphenylyl-N-pyridylacetamideHMDB
anilino-BenzeneHMDB
Benzenamine, N-phenyl-, styrenatedHMDB
Big dipperHMDB
Deccoscald 282HMDB
DFAHMDB
DifenylaminHMDB
DiphenpyramideHMDB
Diphenyl-amineHMDB
Diphenylamine indicatorHMDB
Diphenylamine, acsHMDB
Diphenylamine, reaction product with 2,2,4-trimethylpenteneHMDB
N-FenylanilinHMDB
N-Phenyl-anilineHMDB
N-Phenyl-benzenamineHMDB
N-Phenylbenzenamine, 9ciHMDB
N-Phenylbenzenamine, styrenatedHMDB
N-PhenylbenzeneamineHMDB
Naugalube 428lHMDB
no ScaldHMDB
no Scald dpa 283HMDB
NO-ScaldHMDB
NO-Scald dpa 283HMDB
PhenylanilineHMDB
Poly(diphenylamine)HMDB
Pyridyl-biphenylyl-acetamideHMDB
ScaldipHMDB
Shield dpaHMDB
Styrenated diphenylamineHMDB
Styrene, reaction product with diphenylamineHMDB
Chemical FormulaC12H11N
Average Molecular Weight169.2224
Monoisotopic Molecular Weight169.089149357
IUPAC NameN-phenylaniline
Traditional Namediphenylamine
CAS Registry Number122-39-4
SMILES
N(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChI KeyDMBHHRLKUKUOEG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • Aniline or substituted anilines
  • Secondary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point52 - 54 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.053 mg/mL at 20 °CNot Available
LogP3.50Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP3.34ALOGPS
logP3.41ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.54 m³·mol⁻¹ChemAxon
Polarizability19.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available137.4731661259
DarkChem[M-H]-PredictedNot Available135.69531661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2900000000-0f2d7d76998f0e03ab742017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-86a150c3e0c06fd6c4312017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-8900000000-43ff93288efd91fa24fd2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-2900000000-0f2d7d76998f0e03ab742018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-86a150c3e0c06fd6c4312018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-8900000000-43ff93288efd91fa24fd2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2900000000-95ad298f6a97172946972017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-5900000000-8c8ae83e5ede4467297a2014-09-20View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-336cf3dcad8a94f8f2fe2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-17db2a0cdb58bb5824c32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-3900000000-2a0efcae7cb8dd1770412017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-9800000000-e79da21524f340fefcd42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9200000000-d3f71eb25d134e12dec62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9100000000-5dfcdb1d8c44264cc1532017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-2283250c2cf8e7fdffbd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-2900000000-3a5b94cdf663cbe3bc482017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9200000000-797a3103a29e18b04c1c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-cbc979c9a66db9d0b5c42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-f417cc3873e4f1ad2c802017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00di-0900000000-cf90bb96548b3a94c35b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00di-2900000000-76156abb74c3638533592017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9300000000-30558c8720d9f497b7e02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9200000000-5838e4d5ff5e8f3a93232017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9200000000-9d965a101be070305d882017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00di-0900000000-2228916b18e1afebcbc62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00di-0900000000-12e21d12706763f57b902017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00dl-4900000000-f2aab9a54df33c3c91262017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-00c2a79f600db264c67d2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-3f72bbc5daf7c9fd95582016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4l-9700000000-f5a6b692c949f5a02f602016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-10096022c5cd3d3963742016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-899ac00162614581a4412016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-4f65d69ee98d44ec919f2016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)2014-09-23View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010494
KNApSAcK IDNot Available
Chemspider ID11003
KEGG Compound IDC11016
BioCyc IDCPD-9937
BiGG IDNot Available
Wikipedia LinkDiphenylamine
METLIN IDNot Available
PubChem Compound11487
PDB IDNot Available
ChEBI ID4640
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jitsui Y, Ohtani N: Transmission electron microscope observation of organic-inorganic hybrid thin active layers of light-emitting diodes. Nanoscale Res Lett. 2012 Oct 25;7(1):591. doi: 10.1186/1556-276X-7-591. [PubMed:23095451 ]
  2. Ramon JG, Bittner ER: Excited state calculations on fluorene-based polymer blends: effect of stacking orientation and solvation. J Chem Phys. 2007 May 14;126(18):181101. [PubMed:17508783 ]
  3. Shyla B, Nagendrappa G: Redox spectrophotometric method involving electrolytically generated manganese(III) sulphate with diphenylamine for the determination of ascorbic acid present in the samples of various fruits, commercial juices and sprouted food grains. Food Chem. 2013 Jun 1;138(2-3):2036-42. doi: 10.1016/j.foodchem.2012.11.076. Epub 2012 Nov 24. [PubMed:23411340 ]
  4. Authors unspecified: para-Nitrosodiphenylamine. IARC Monogr Eval Carcinog Risk Chem Hum. 1982 Apr;27:227-33. [PubMed:6955265 ]
  5. Nagata T, Masuda K, Maeno S, Miura I: Synthesis and structure-activity study of fungicidal anilinopyrimidines leading to mepanipyrim (KIF-3535) as an anti-Botrytis agent. Pest Manag Sci. 2004 Apr;60(4):399-407. [PubMed:15119603 ]
  6. Benson-Smith JJ, Wilson J, Dyer-Smith C, Mouri K, Yamaguchi S, Murata H, Nelson J: Long-lived exciplex formation and delayed exciton emission in bulk heterojunction blends of silole derivative and polyfluorene copolymer: the role of morphology on exciplex formation and charge separation. J Phys Chem B. 2009 Jun 4;113(22):7794-9. doi: 10.1021/jp808671f. [PubMed:19435328 ]
  7. Huang YS, Westenhoff S, Avilov I, Sreearunothai P, Hodgkiss JM, Deleener C, Friend RH, Beljonne D: Electronic structures of interfacial states formed at polymeric semiconductor heterojunctions. Nat Mater. 2008 Jun;7(6):483-9. doi: 10.1038/nmat2182. Epub 2008 Apr 27. [PubMed:18438413 ]
  8. Lin Y, El-Khouly ME, Chen Y, Supur M, Gu L, Li Y, Fukuzumi S: A new cyanofluorene-triphenylamine copolymer: synthesis and photoinduced intramolecular electron transfer processes. Chemistry. 2009 Oct 19;15(41):10818-24. doi: 10.1002/chem.200900752. [PubMed:19760714 ]
  9. Liu B, Najari A, Pan C, Leclerc M, Xiao D, Zou Y: New low bandgap dithienylbenzothiadiazole vinylene based copolymers: synthesis and photovoltaic properties. Macromol Rapid Commun. 2010 Feb 16;31(4):391-8. doi: 10.1002/marc.200900654. Epub 2009 Nov 24. [PubMed:21590919 ]
  10. Dalby O, Birkett JW: The evaluation of solid phase micro-extraction fibre types for the analysis of organic components in unburned propellant powders. J Chromatogr A. 2010 Nov 12;1217(46):7183-8. doi: 10.1016/j.chroma.2010.09.012. Epub 2010 Sep 15. [PubMed:20933233 ]
  11. Fun HK, Chantrapromma S, D'Silva ED, Patil PS, Dharmaprakash SM: S-Benzyl-thiouronium 4-anilinobenzene-sulfonate. Acta Crystallogr Sect E Struct Rep Online. 2008 Aug 30;64(Pt 9):o1858-9. doi: 10.1107/S160053680802727X. [PubMed:21201828 ]
  12. Hirai Y, Uozumi Y: Heterogeneous aromatic amination of aryl halides with arylamines in water with PS-PEG resin-supported palladium complexes. Chem Asian J. 2010 Aug 2;5(8):1788-95. doi: 10.1002/asia.201000192. [PubMed:20572283 ]
  13. Jin R, Levermore PA, Huang J, Wang X, Bradley DD, deMello JC: On the use and influence of electron-blocking interlayers in polymer light-emitting diodes. Phys Chem Chem Phys. 2009 May 14;11(18):3455-62. doi: 10.1039/b819200f. Epub 2009 Mar 6. [PubMed:19421548 ]
  14. Sedinova V, Urbanova E, Skarda J, Jukl A: [Determination of the number of somatic cells in milk using the rapid diphenylamine DNA filter method]. Vet Med (Praha). 1985 Aug;30(8):467-75. [PubMed:3929447 ]
  15. Agarwala S, Peh CK, Ho GW: Investigation of ionic conductivity and long-term stability of a LiI and KI coupled diphenylamine quasi-solid-state dye-sensitized solar cell. ACS Appl Mater Interfaces. 2011 Jul;3(7):2383-91. doi: 10.1021/am200296f. Epub 2011 Jun 20. [PubMed:21648469 ]
  16. Marjanovic B, Juranic I, Ciric-Marjanovic G: Revised mechanism of Boyland-Sims oxidation. J Phys Chem A. 2011 Apr 21;115(15):3536-50. doi: 10.1021/jp111129t. Epub 2011 Mar 24. [PubMed:21434676 ]
  17. Kim JS, Lu L, Sreearunothai P, Seeley A, Yim KH, Petrozza A, Murphy CE, Beljonne D, Cornil J, Friend RH: Optoelectronic and charge transport properties at organic-organic semiconductor interfaces: comparison between polyfluorene-based polymer blend and copolymer. J Am Chem Soc. 2008 Oct 1;130(39):13120-31. doi: 10.1021/ja803766j. Epub 2008 Sep 4. [PubMed:18767836 ]
  18. Patterson J, Mura C: Rapid colorimetric assays to qualitatively distinguish RNA and DNA in biomolecular samples. J Vis Exp. 2013 Feb 4;(72):e50225. doi: 10.3791/50225. [PubMed:23407542 ]
  19. Lee KP, Gopalan AI, Kim KS, Santhosh P: Synthesis and characterization of processable multi-walled carbon nanotubes-sulfonated polydiphenylamine graft copolymers. J Nanosci Nanotechnol. 2007 Oct;7(10):3386-93. [PubMed:18330145 ]
  20. Abid-Essefi S, Bouaziz C, Golli-Bennour EE, Ouanes Z, Bacha H: Comparative study of toxic effects of zearalenone and its two major metabolites alpha-zearalenol and beta-zearalenol on cultured human Caco-2 cells. J Biochem Mol Toxicol. 2009 Jul-Aug;23(4):233-43. doi: 10.1002/jbt.20284. [PubMed:19705349 ]
  21. Philips MF, Gopalan AI, Lee KP: Development of a novel cyano group containing electrochemically deposited polymer film for ultrasensitive simultaneous detection of trace level cadmium and lead. J Hazard Mater. 2012 Oct 30;237-238:46-54. doi: 10.1016/j.jhazmat.2012.07.069. Epub 2012 Aug 24. [PubMed:22964385 ]
  22. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .