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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:50:30 UTC
Update Date2022-03-07 02:53:23 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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point52 - 54 °CNot Available
Boiling Point302.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.053 mg/mL at 20 °CNot Available
LogP3.50Not Available
Experimental Chromatographic PropertiesNot 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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.4731661259
DarkChem[M-H]-135.69531661259
DeepCCS[M+H]+134.85130932474
DeepCCS[M-H]-132.30630932474
DeepCCS[M-2H]-168.06930932474
DeepCCS[M+Na]+142.81830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiphenylamineN(C1=CC=CC=C1)C1=CC=CC=C12440.0Standard polar33892256
DiphenylamineN(C1=CC=CC=C1)C1=CC=CC=C11608.4Standard non polar33892256
DiphenylamineN(C1=CC=CC=C1)C1=CC=CC=C11656.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diphenylamine,1TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC=C11649.6Semi standard non polar33892256
Diphenylamine,1TMS,isomer #1C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC=C11710.1Standard non polar33892256
Diphenylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC=C11833.5Semi standard non polar33892256
Diphenylamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC=C11892.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diphenylamine EI-B (Non-derivatized)splash10-014i-2900000000-0f2d7d76998f0e03ab742017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diphenylamine EI-B (Non-derivatized)splash10-014i-0900000000-86a150c3e0c06fd6c4312017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diphenylamine EI-B (Non-derivatized)splash10-014i-8900000000-43ff93288efd91fa24fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diphenylamine EI-B (Non-derivatized)splash10-014i-2900000000-0f2d7d76998f0e03ab742018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diphenylamine EI-B (Non-derivatized)splash10-014i-0900000000-86a150c3e0c06fd6c4312018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diphenylamine EI-B (Non-derivatized)splash10-014i-8900000000-43ff93288efd91fa24fd2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2900000000-95ad298f6a97172946972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diphenylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-5900000000-8c8ae83e5ede4467297a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-336cf3dcad8a94f8f2fe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-17db2a0cdb58bb5824c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QFT , positive-QTOFsplash10-00di-3900000000-2a0efcae7cb8dd1770412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QFT , positive-QTOFsplash10-006x-9800000000-e79da21524f340fefcd42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QFT , positive-QTOFsplash10-0006-9200000000-d3f71eb25d134e12dec62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QFT , positive-QTOFsplash10-0006-9100000000-5dfcdb1d8c44264cc1532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QQ , positive-QTOFsplash10-00di-0900000000-2283250c2cf8e7fdffbd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QQ , positive-QTOFsplash10-00di-2900000000-3a5b94cdf663cbe3bc482017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QQ , positive-QTOFsplash10-0006-9200000000-797a3103a29e18b04c1c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-cbc979c9a66db9d0b5c42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-f417cc3873e4f1ad2c802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-00di-0900000000-cf90bb96548b3a94c35b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-00di-2900000000-76156abb74c3638533592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-0006-9300000000-30558c8720d9f497b7e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-0006-9200000000-5838e4d5ff5e8f3a93232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-0006-9200000000-9d965a101be070305d882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-00di-0900000000-2228916b18e1afebcbc62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-00di-0900000000-12e21d12706763f57b902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diphenylamine ESI-ITFT , positive-QTOFsplash10-00dl-4900000000-f2aab9a54df33c3c91262017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylamine 10V, Positive-QTOFsplash10-00di-0900000000-00c2a79f600db264c67d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylamine 20V, Positive-QTOFsplash10-00di-0900000000-3f72bbc5daf7c9fd95582016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylamine 40V, Positive-QTOFsplash10-0v4l-9700000000-f5a6b692c949f5a02f602016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylamine 10V, Negative-QTOFsplash10-014i-0900000000-10096022c5cd3d3963742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylamine 20V, Negative-QTOFsplash10-014i-0900000000-899ac00162614581a4412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diphenylamine 40V, Negative-QTOFsplash10-014i-5900000000-4f65d69ee98d44ec919f2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
Good Scents IDrw1021201
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  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 ]
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  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 ]
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  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 ]
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  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 ]
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