Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:11 UTC |
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Update date | 2020-09-17 15:34:49 UTC |
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Primary ID | FDB012457 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Benzeneacetonitrile |
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Description | Benzyl 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). 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. |
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CAS Number | 140-29-4 |
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Structure | |
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Synonyms | Synonym | Source |
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(Cyanomethyl)benzene | ChEBI | 2-Phenylacetonitrile | ChEBI | alpha-Cyanotoluene | ChEBI | alpha-Tolunitrile | ChEBI | Benzyl cyanide | ChEBI | Benzyl nitrile | ChEBI | a-Cyanotoluene | Generator | Α-cyanotoluene | Generator | a-Tolunitrile | Generator | Α-tolunitrile | Generator | .omega.-cyanotoluene | HMDB | Acetic acid, phenyl-nitrile | HMDB | alpha -Cyanotoluene | HMDB | alpha -Tolunitrile | HMDB | alpha-cyano-Toluene | HMDB | Benzeneacetonitrile, 9ci | HMDB | Benzylkyanid | HMDB | Benzylnitrile | HMDB | Cyanophenylmethane | HMDB | Enzylcyanide | HMDB | laquo omegaraquo -Cyanotoluene | HMDB | Omega-cyanotoluene | HMDB | Phenacetonitrile | HMDB | Phenyl acetyl nitrile | HMDB | Phenyl-acetonitrile | HMDB | Phenylacetonitrile | HMDB | Phenylacetonitrile, liquid | HMDB | Benzeneacetonitrile | ChEBI | α-cyano- | biospider | α-cyanotoluene | biospider | α-tolunitrile | biospider | «omega»-cyanotoluene | biospider | Acetonitrile, phenyl- | biospider | alpha-Cyano-toluene | HMDB | Alpha-cyanotoluene | biospider | Alpha-tolunitrile | biospider | Benzeneacetonitrile, 9CI | db_source | Laquo omegaraquo -cyanotoluene | HMDB | Phenylacetonitrile, liquid [UN2470] [Poison] | biospider | Toluene, α-cyano- | biospider | Toluene, alpha-cyano- | biospider | α-cyanotoluene | Generator | α-tolunitrile | Generator |
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Predicted Properties | |
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Chemical Formula | C8H7N |
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IUPAC name | 2-phenylacetonitrile |
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InChI Identifier | InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 |
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InChI Key | SUSQOBVLVYHIEX-UHFFFAOYSA-N |
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Isomeric SMILES | N#CCC1=CC=CC=C1 |
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Average Molecular Weight | 117.1479 |
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Monoisotopic Molecular Weight | 117.057849229 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzyl cyanides |
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Direct Parent | Benzyl cyanides |
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Alternative Parents | |
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Substituents | - Benzyl-cyanide
- Nitrile
- Carbonitrile
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Environmental role: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 82.02%; H 6.02%; N 11.96% | DFC |
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Melting Point | -23.8 oC | |
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Boiling Point | Bp12 107° | DFC |
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Experimental Water Solubility | 0.1 mg/mL at 25 oC | CHEMICALS INSPECTION AND TESTING INSTITU (1992) |
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Experimental logP | 1.56 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d1515 1.02 | DFC |
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Refractive Index | n25D 1.5211 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-014i-9600000000-bacbbfee69800587e876 | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-9700000000-aa951610ae3086079fc3 | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-6900000000-9fa568274538519d6221 | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-4900000000-7fb420e2a4693843bcc6 | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-9700000000-44dc07c52f713661d49d | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-9700000000-aa951610ae3086079fc3 | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-6900000000-9fa568274538519d6221 | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-4900000000-7fb420e2a4693843bcc6 | Spectrum | GC-MS | Benzeneacetonitrile, non-derivatized, GC-MS Spectrum | splash10-014i-9700000000-44dc07c52f713661d49d | Spectrum | Predicted GC-MS | Benzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-9600000000-3ff8c2a019af8041ccf5 | Spectrum | Predicted GC-MS | Benzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Benzeneacetonitrile, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-26618186da25d2fb36a3 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-2900000000-36bcc9666d8d6f02be93 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9100000000-e64aaf4670bfdd42e5ec | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-c300e5c9a5a8fd9efed7 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-1900000000-62ae29742c669f0cbb48 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kr-9400000000-a31fa80a0b41e8872dfd | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-89c3f30c8225ba6d5d62 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0900000000-89c3f30c8225ba6d5d62 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-7900000000-a5d53547c4ff1f8c5b08 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kf-9600000000-37eae74477faef6aa26e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9200000000-0ed055b02df43a8a2055 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00kf-9000000000-c6037f271472539420c4 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 13839308 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C16074 |
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Pubchem Compound ID | 8794 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 25979 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB34171 |
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CRC / DFC (Dictionary of Food Compounds) ID | FDG02-B:HHB12-D |
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EAFUS ID | Not Available |
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Dr. Duke ID | BENZYL-CYANIDE|PHENYLACETONITRILE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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