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Showing NP-Card for Benzyl nitrile (NP0045124)

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Record Information
Version2.0
Created at2022-03-10 18:58:23 UTC
Updated at2022-03-10 22:18:24 UTC
NP-MRD IDNP0045124
Secondary Accession NumbersNone
Natural Product Identification
Common NameBenzyl nitrile
DescriptionBenzyl nitrile or Benzeneacetonitrile, also known as benzyl cyanide or alpha-cyanotoluene, belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group. Benzeneacetonitrile is found, on average, in the highest concentration within kohlrabis and peppermints. Benzeneacetonitrile has also been detected, but not quantified, in several different foods, such as cabbages, cauliflowers, garden and cherry tomato. Benzeneacetonitrile has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://Doi.Org/10.1007/978-1-59259-947-9_2). Benzeneacetonitrile is a potentially toxic compound. Benzyl nitrile is a colorless oily aromatic liquid and an important precursor to numerous compounds in organic chemistry. Benzyl nitrile is a useful precursor to numerous drugs with recreational use potential. Benzyl nitrile can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045124 (Benzyl nitrile)


  Mrv1652309272007382D          

  9  9  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4378    1.9294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  3  0  0  0  0
M  END
Download

3D MOL for NP0045124 (Benzyl nitrile)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    3.4018    0.2508   -1.5306 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540    0.1247   -0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271   -0.0292    0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670   -0.0163    0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2123   -1.1807   -0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5603   -1.2080   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835   -0.0350   -0.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290    1.1476   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2654    1.1559    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2148   -0.9587    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604    0.8178    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612   -2.1112   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -2.1326   -0.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3553   -0.0001   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465    2.0942   -0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2658    2.0809    0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  3 10  1  0
  3 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
M  END
Download

3D SDF for NP0045124 (Benzyl nitrile)


  Mrv1652309272007382D          

  9  9  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4378    1.9294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0045124

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N#CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2

> <INCHI_KEY>
SUSQOBVLVYHIEX-UHFFFAOYSA-N

> <FORMULA>
C8H7N

> <MOLECULAR_WEIGHT>
117.1479

> <EXACT_MASS>
117.057849229

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
12.748219872683695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenylacetonitrile

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.6689429719999997

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.333495948741568

> <JCHEM_POLAR_SURFACE_AREA>
23.79

> <JCHEM_REFRACTIVITY>
36.3449

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetonitrile

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045124 (Benzyl nitrile)

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PDB for NP0045124 (Benzyl nitrile)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.750   3.602   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.084   2.832   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.417   3.602   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0045124 (Benzyl nitrile)
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SMILES for NP0045124 (Benzyl nitrile)
N#CCC1=CC=CC=C1
Download
INCHI for NP0045124 (Benzyl nitrile)
InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
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View in JSmol
Synonyms
ValueSource
(Cyanomethyl)benzeneChEBI
2-PhenylacetonitrileChEBI
alpha-CyanotolueneChEBI
alpha-TolunitrileChEBI
Benzyl cyanideChEBI
Benzyl nitrileChEBI
a-CyanotolueneGenerator
Α-cyanotolueneGenerator
a-TolunitrileGenerator
Α-tolunitrileGenerator
.omega.-cyanotolueneHMDB
Acetic acid, phenyl-nitrileHMDB
alpha -CyanotolueneHMDB
alpha -TolunitrileHMDB
alpha-Cyano-tolueneHMDB
Benzeneacetonitrile, 9ciHMDB
BenzylkyanidHMDB
BenzylnitrileHMDB
CyanophenylmethaneHMDB
EnzylcyanideHMDB
Laquo omegaraquo -cyanotolueneHMDB
Omega-cyanotolueneHMDB
PhenacetonitrileHMDB
Phenyl acetyl nitrileHMDB
Phenyl-acetonitrileHMDB
PhenylacetonitrileHMDB
Phenylacetonitrile, liquidHMDB
BenzeneacetonitrileChEBI
Chemical FormulaC8H7N
Average Mass117.1479 Da
Monoisotopic Mass117.05785 Da
IUPAC Name2-phenylacetonitrile
Traditional Namephenylacetonitrile
CAS Registry Number140-29-4
SMILES
N#CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
InChI KeySUSQOBVLVYHIEX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Alyssum desertorumLOTUS Database
Arabidopsis thalianaLOTUS Database
Beta vulgarisLOTUS Database
Botrytis cinereaLOTUS Database
Brassica oleracea var. botrytisFooDB
    • L. Valettea X. Fernandez, S. Poulain, A.-M. Loiseau, L. Lizzani-Cuvelier, R. Levieil, L. Restier....
Brassica oleracea var. gongylodesFooDB
Cannabis sativaNULL
      Not Available
Carica papayaLOTUS Database
Carica papaya L.FooDB
Citrus limonLOTUS Database
Hesperis matronalisLOTUS Database
Inula racemosaLOTUS Database
Jasminum grandiflorumPlant
Lepidium meyeniiLOTUS Database
Lepidium sativumFooDB
Mentha x piperitaFooDB
Murraya paniculataPlant
Nicotiana bonariensisLOTUS Database
Pandanus tectoriusLOTUS Database
Parthenium hysterophorusLOTUS Database
Plumeria rubraLOTUS Database
Popillia japonicaLOTUS Database
Salvadora persicaLOTUS Database
Schistocerca gregariaLOTUS Database
Sinapis albaLOTUS Database
Solanum lycopersicum var. lycopersicumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzyl cyanides  
Direct ParentBenzyl cyanides  
Alternative Parents
Substituents
  • Benzyl-cyanide
    • 

  • Nitrile
    • 

  • Carbonitrile
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP1.42ALOGPS
logP1.67ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)14.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.34 m³·mol⁻¹ChemAxon
Polarizability12.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034171  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012457  
KNApSAcK IDC00007674  
Chemspider ID13839308  
KEGG Compound IDC16074  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8794  
PDB IDNot Available
ChEBI ID25979  
Good Scents IDNot Available
References
General References
  1. Seidelmann K, Ferenz HJ: Courtship inhibition pheromone in desert locusts, Schistocerca gregaria. J Insect Physiol. 2002 Nov;48(11):991-996. doi: 10.1016/s0022-1910(02)00178-6. [PubMed:12770022  ] 
  2. Tobisu M, Nakamura R, Kita Y, Chatani N: Rhodium-catalyzed reductive cleavage of carbon-cyano bonds with hydrosilane: a catalytic protocol for removal of cyano groups. J Am Chem Soc. 2009 Mar 11;131(9):3174-5. doi: 10.1021/ja810142v. [PubMed:19215138  ] 
  3. He YC, Zhang ZJ, Xu JH, Liu YY: Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401. J Ind Microbiol Biotechnol. 2010 Jul;37(7):741-50. doi: 10.1007/s10295-010-0720-y. Epub 2010 Apr 22. [PubMed:20411403  ] 
  4. Kugimiya S, Shimoda T, Tabata J, Takabayashi J: Present or past herbivory: a screening of volatiles released from Brassica rapa under caterpillar attacks as attractants for the solitary parasitoid, Cotesia vestalis. J Chem Ecol. 2010 Jun;36(6):620-8. doi: 10.1007/s10886-010-9802-6. Epub 2010 May  20. [PubMed:20490899  ] 
  5. Kaplan O, Bezouska K, Malandra A, Vesela AB, Petrickova A, Felsberg J, Rinagelova A, Kren V, Martinkova L: Genome mining for the discovery of new nitrilases in filamentous fungi. Biotechnol Lett. 2011 Feb;33(2):309-12. doi: 10.1007/s10529-010-0421-7. Epub 2010 Sep 30. [PubMed:20882316  ] 
  6. Vivekanand PA, Wang ML: Sonocatalyzed synthesis of 2-phenylvaleronitrile under controlled reaction conditions--a kinetic study. Ultrason Sonochem. 2011 Sep;18(5):1241-8. doi: 10.1016/j.ultsonch.2011.02.002. Epub 2011 Feb 17. [PubMed:21377400  ] 
  7. Huigens ME, de Swart E, Mumm R: Risk of egg parasitoid attraction depends on anti-aphrodisiac titre in the large cabbage white butterfly Pieris brassicae. J Chem Ecol. 2011 Apr;37(4):364-7. doi: 10.1007/s10886-011-9935-2. Epub 2011 Mar  31. [PubMed:21452001  ] 
  8. Huang L, Liu Y, Xie F, Hu Y: An organic molecule modulated chemoselective cyclization of alkynyl nitriles tethered to 2-alkyl substituted chromones with multireactive sites. Org Lett. 2012 Dec 21;14(24):6122-5. doi: 10.1021/ol302964x. Epub 2012 Dec 4. [PubMed:23210678  ] 
  9. Rao CN, Hoz S: Photostimulated reduction of nitriles by SmI2. J Org Chem. 2012 Apr 20;77(8):4029-34. doi: 10.1021/jo300383r. Epub 2012 Apr 11. [PubMed:22468753  ] 
  10. Petrickova A, Vesela AB, Kaplan O, Kubac D, Uhnakova B, Malandra A, Felsberg J, Rinagelova A, Weyrauch P, Kren V, Bezouska K, Martinkova L: Purification and characterization of heterologously expressed nitrilases from filamentous fungi. Appl Microbiol Biotechnol. 2012 Feb;93(4):1553-61. doi: 10.1007/s00253-011-3525-7. Epub 2011 Sep 3. [PubMed:21892598  ] 
  11. Amwayi PW, Masiga DK, Govender P, Teal PE, Torto B: Mass spectral determination of phenylacetonitrile (PAN) levels in body tissues of adult desert locust, Schistocerca gregaria. J Insect Physiol. 2012 Aug;58(8):1037-41. doi: 10.1016/j.jinsphys.2012.03.012. Epub 2012 May 17. [PubMed:22609420  ] 
  12. Noge K, Abe M, Tamogami S: Phenylacetonitrile from the giant knotweed, Fallopia sachalinensis, infested by the Japanese beetle, Popillia japonica, is induced by exogenous methyl jasmonate. Molecules. 2011 Aug 3;16(8):6481-8. doi: 10.3390/molecules16086481. [PubMed:21814160  ]