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2-Naphthol (FDB000877)

Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2018-05-28 22:36:45 UTC
Primary IDFDB000877
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Naphthol
DescriptionTrace constituent of essential oils 2-Naphthol is a colorless crystalline solid and an isomer of 1-naphthol, differing by the location of the hydroxyl group on naphthalene. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. 2-Naphthol has several different uses including dyes, pigments, fats, oils, insecticides, pharmaceuticals, perfumes, antiseptics, synthesis of fungicides, and antioxidants for rubber. Detection of 2-Naphthol in urine usually results from long-term persistent exposure to pesticides such as chlorpyrifos, but also due to exposure to naphthalene in older types of mothballs, fires that produce polyaromatic hydrocarbons (PAHs), and tobacco smoke.; 2-Naphthol, or ?-naphthol, is a colorless crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on naphthalene. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They can be used in the production of dyes and in organic synthesis. For example, 2-naphthol reacts to form BINOL.
CAS Number135-19-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP2.93ALOGPS
logP2.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.49 m³·mol⁻¹ChemAxon
Polarizability15.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H8O
IUPAC namenaphthalen-2-ol
InChI IdentifierInChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H
InChI KeyJWAZRIHNYRIHIV-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=CC=CC=C2C=C1
Average Molecular Weight144.1699
Monoisotopic Molecular Weight144.057514878
Classification
Description Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthols and derivatives
Direct ParentNaphthols and derivatives
Alternative Parents
Substituents
  • 2-naphthol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Indirect biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.31%; H 5.59%; O 11.10%DFC
Melting PointMp 123°DFC
Boiling PointBp 285-286°DFC
Experimental Water Solubility0.755 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.70HANSCH,C ET AL. (1995)
Experimental pKa9.51
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-3900000000-9ba2c98085c1cfb979ae2014-09-20View Spectrum
GC-MS2-Naphthol, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-59876f73d937e3fff0c1Spectrum
GC-MS2-Naphthol, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-59876f73d937e3fff0c1Spectrum
Predicted GC-MS2-Naphthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-0900000000-2b4afdf032e4268cf0dbSpectrum
Predicted GC-MS2-Naphthol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-8950000000-be69afc3a0e419124c04Spectrum
Predicted GC-MS2-Naphthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Naphthol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0900000000-150b753c58953122f7a02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0002-0900000000-3ed11eab13f522e296d02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0002-0900000000-76ad2ee08369a5c727272020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-014j-0900000000-668149fa5169e936b8cc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014i-0900000000-818a664d833b009956ca2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-014i-1900000000-cfdbc5ded35ac6d127e82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-016u-3900000000-7581b81c891ce2121e302020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-016u-6900000000-ecc855690e59bfdd55982020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-016u-9800000000-68d9b962e8fe933361262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-016r-9400000000-9eeb688197da71b8a3bc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-0900000000-820d3a81dfc9463584eb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-000i-9000000000-41143d019e9e3192e3a92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-014i-0900000000-8a33e2a4035f1d5db4c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00kf-0900000000-b57369b32440fe60da1d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-95369892ad06085feeaa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-0900000000-4359d09beb852a6b4d8d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014j-1900000000-3f45d855eafad75b3a672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014j-2900000000-949ec470c0e3ac2ca5b22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0900000000-ec57dc12ddf60a2741f02021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-7b3aeb4e0f86148dab682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-a5c6a08b3ea484ba1d0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-2900000000-ecd1849d7a9f7a9bcac82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e1a1f37ba96a4bf71d702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-019880a3b2ccbcc83a872016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider ID8341
ChEMBL IDCHEMBL14126
KEGG Compound IDC11713
Pubchem Compound ID8663
Pubchem Substance IDNot Available
ChEBI ID10432
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12322
CRC / DFC (Dictionary of Food Compounds) IDBLN50-J:BLN50-J
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID03V
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID2-Naphthol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference