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Showing NP-Card for o-tolunitrile (NP0254380)

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Record Information
Version1.0
Created at2022-09-07 18:31:51 UTC
Updated at2022-09-07 18:31:51 UTC
NP-MRD IDNP0254380
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-tolunitrile
DescriptionO-Tolunitrile belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent. Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. Benzyl cyanide is regulated in the United States as a DEA List I chemical. The partial hydrolysis of BnCN results in 2-phenylacetamide, a known anticonvulsant. Benzyl cyanide, like related benzyl derivatives, is an irritant to the skin and eyes. O-Tolunitrile is possibly neutral. Benzyl cyanide is a useful precursor to numerous pharmaceuticals. Examples include:Anorectics (e.G. Sibutramine)Analgesics (e.G. Ethoheptazine, ketobemidone, pethidine, and phenoperidine)Antiarrhythmics (e.G. Disopyramide)Antidepressants (e.G. Venlafaxine)Antihistamines (e.G. Levocabastine and chlorphenamine)Antimalarial medications (e.G. Pyrimethamine)Antitussives (e.G. Isoaminile, oxeladin, butethamate, pentapiperide, and pentoxyverine)Diuretics (e.G. Triamterene)Hypnotics (e.G. Alonimid and phenobarbital)Spasmolytics (e.G. Pentapiperide and drofenine)Stimulants (e.G. Methylphenidate)AzatadineBecause benzyl cyanide is a useful precursor to numerous drugs with recreational use potential, many countries strictly regulate the compound. Benzyl cyanide can be hydrolyzed to give phenylacetic acid or used in the Pinner reaction to yield phenylacetic acid esters. Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine. The compound also forms an "active methylene unit" on the carbon between the aromatic ring and the nitrile functional group. o-tolunitrile is found in Festuca rubra and Glycyrrhiza glabra. It is toxic and produces the deadly poison hydrogen cyanide when burned.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0254380 (o-tolunitrile)


  Mrv1652304272018582D          

  9  9  0  0  0  0            999 V2000
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  2  0  0  0  0
  6  8  1  0  0  0  0
  6  9  3  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0254380 (o-tolunitrile)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.0266    0.4929    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5645    0.3364    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3018    1.4063    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580    1.2612   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1282   -0.0349   -0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678   -1.1047   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -0.9431   -0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9849   -2.0847   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6890   -3.0069   -0.0545 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846    1.5089    0.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149    0.2648    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5441   -0.2956   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0607    2.4267    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    2.0699   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -0.1701   -0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6410   -2.1272   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  3  0
  7  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
M  END
Download

3D SDF for NP0254380 (o-tolunitrile)


  Mrv1652304272018582D          

  9  9  0  0  0  0            999 V2000
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  2  0  0  0  0
  6  8  1  0  0  0  0
  6  9  3  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=CC=C1C#N

> <INCHI_IDENTIFIER>
InChI=1S/C8H7N/c1-7-4-2-3-5-8(7)6-9/h2-5H,1H3

> <INCHI_KEY>
NWPNXBQSRGKSJB-UHFFFAOYSA-N

> <FORMULA>
C8H7N

> <MOLECULAR_WEIGHT>
117.151

> <EXACT_MASS>
117.057849229

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.82855795577897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbenzonitrile

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
2.3427633936666665

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
23.79

> <JCHEM_REFRACTIVITY>
36.820800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methylbenzonitrile

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0254380 (o-tolunitrile)

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PDB for NP0254380 (o-tolunitrile)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.620   0.000   0.000  0.00  0.00           N+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    8    9                                                       
CONECT    7    1    4    8                                                  
CONECT    8    5    6    7                                                  
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0254380 (o-tolunitrile)
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SMILES for NP0254380 (o-tolunitrile)
CC1=CC=CC=C1C#N
Download
INCHI for NP0254380 (o-tolunitrile)
InChI=1S/C8H7N/c1-7-4-2-3-5-8(7)6-9/h2-5H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H7N
Average Mass117.1510 Da
Monoisotopic Mass117.05785 Da
IUPAC Name2-methylbenzonitrile
Traditional Name2-methylbenzonitrile
CAS Registry NumberNot Available
SMILES
CC1=CC=CC=C1C#N
InChI Identifier
InChI=1S/C8H7N/c1-7-4-2-3-5-8(7)6-9/h2-5H,1H3
InChI KeyNWPNXBQSRGKSJB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Festuca rubraLOTUS Database
Glycyrrhiza glabraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzonitriles  
Direct ParentBenzonitriles  
Alternative Parents
Substituents
  • Benzonitrile
    • 

  • Toluene
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.87ALOGPS
logP2.34ChemAxon
logS-1.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.82 m³·mol⁻¹ChemAxon
Polarizability12.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzyl cyanide  
METLIN IDNot Available
PubChem Compound10721  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]