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Benzyl cyanide information


Benzyl cyanide
Skeletal formula of benzyl cyanide
Ball-and-stick model of the benzyl cyanide molecule
Names
Preferred IUPAC name
Phenylacetonitrile[1]
Other names
Benzyl cyanide[1]
2-Phenylacetonitrile
α-Tolunitrile
Benzylnitrile
Identifiers
CAS Number
  • 140-29-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:25979 checkY
ChemSpider
  • 13839308 checkY
ECHA InfoCard 100.004.919 Edit this at Wikidata
KEGG
  • C16074 checkY
PubChem CID
  • 8794
UNII
  • 23G40PRP93 checkY
CompTox Dashboard (EPA)
  • DTXSID2021492 Edit this at Wikidata
InChI
  • InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 checkY
    Key: SUSQOBVLVYHIEX-UHFFFAOYSA-N checkY
  • InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
    Key: SUSQOBVLVYHIEX-UHFFFAOYAJ
SMILES
  • N#CCc1ccccc1
Properties
Chemical formula
C8H7N
Molar mass 117.15 g/mol
Appearance Colorless oily liquid
Density 1.015 g/cm3
Melting point −24 °C (−11 °F; 249 K)
Boiling point 233 to 234 °C (451 to 453 °F; 506 to 507 K)
Magnetic susceptibility (χ)
-76.87·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry.[2] It is also an important pheromone in certain species.[3]

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 16. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a17_363. ISBN 3527306730.
  3. ^ https://www.mpg.de/20278575/0504-choe-chemisches-signal-schuetzt-wanderheuschrecken-vor-kannibalismus

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Benzyl cyanide

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Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor...

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Sodium cyanide

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Illustrative is the synthesis of benzyl cyanide by the reaction of benzyl chloride and sodium cyanide. Being highly toxic, sodium cyanide is used to kill or stun...

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Benzyl chloride

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pharmaceuticals, is produced from benzyl cyanide, which in turn is generated by treatment of benzyl chloride with sodium cyanide. Quaternary ammonium salts,...

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Retrosynthetic analysis

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has been synthesized from benzyl cyanide, itself prepared by the analogous reaction of benzyl bromide with sodium cyanide. Manipulation of functional...

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Snyder's Organic Syntheses (published 1955), involves the reduction of benzyl cyanide with hydrogen in liquid ammonia, in the presence of a Raney-Nickel catalyst...

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Isocyanide

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isocyanides have substantial acidity. For example, benzyl isocyanide has a pKa of 27.4. In comparison, benzyl cyanide has a pKa of 21.9. In the gas phase, CH3NC...

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Cyanation

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synthesis of benzyl cyanide by the reaction of benzyl chloride and sodium cyanide. In some cases cuprous cyanide is used instead of sodium cyanide. Cyanation...

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Nitrile reduction

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Krishnan; A. Muthukumaran; H. V. K. Udupa (1979). "The electroreduction of benzyl cyanide on iron and cobalt cathodes". Journal of Applied Electrochemistry. 9...

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EPA list of extremely hazardous substances

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Benzimidazole, 4,5-dichloro-2-(trifluoromethyl)- Benzotrichloride Benzyl chloride Benzyl cyanide Bicyclo(2.2.1)heptane-2-carbonitrile Bis(chloromethyl) ketone...

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approaches using benzyl cyanide as a starting material have been developed: The first of these methods consists of a Pinner reaction of benzyl cyanide, giving...

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Mesogen

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(SmB/I/F/G/H) phases. An example of a calamitic mesogen type rigid core is a benzyl cyanide based rod molecule, where the smectic A liquid crystal phase exists...

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DEA list of chemicals

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used in the manufacture of controlled substances: Acetic anhydride Acetone Benzyl chloride Diethyl ether Potassium permanganate 2-Butanone (or methyl ethyl...

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other organisms. This compound may be prepared by the hydrolysis of benzyl cyanide: Phenylacetic acid undergoes ketonic decarboxylation to form ketones...

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Precursor chemicals

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Anthranilic acid methaqualone Benzaldehyde amphetamine phenylacetone Benzyl cyanide phenylacetone CBD (see comparison of phytocannabinoids) THC Ephedrine...

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Photochlorination

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the mono-substituted benzyl chloride, which is hydrolyzed to benzyl alcohol. Benzyl chloride can also be converted via benzyl cyanide with subsequent hydrolysis...

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Etonitazene

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cyanide). The imino ether, 2-(4-Ethoxyphenyl)-acetimidic acid ethyl ester hydrochloride, is prepared by dissolving the 4-substituted benzyl cyanide in...

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Electrosynthesis

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nitrile to a primary amine in a divided cell; the cathodic reduction of benzyl cyanide to phenethylamine is shown: Cathodic reduction of a nitroalkene can...

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Nitrile

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group are not called nitriles, but cyanides instead. Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly...

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C8H7N

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C8H7N (molar mass: 117.15 g/mol, exact mass: 117.0578 u) may refer to: Benzyl cyanide (BnCN) Indole Indolizine Isoindole This set index page lists chemical...

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Pethidine

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be produced in a two-step synthesis. The first step is reaction of benzyl cyanide and chlormethine in the presence of sodium amide to form a piperidine...

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(aka lachrymatory agent or lachrymator). Benzyl chloride Benzyl bromide Bromoacetone (BA) Bromobenzyl cyanide (CA) Bromomethyl ethyl ketone Capsaicin (OC)...

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Umpolung

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as a nucleophile in nucleophilic displacement with alkyl halides such as benzyl bromide, with other carbonyl compounds such as cyclohexanone or oxiranes...

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reusable. As a model reaction, the reaction of benzyl azide with 4-toluenesulfonic acid cyanide forming 1-benzyl-5-(4-toluenesulfonyl)tetrazole was investigated...

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Pentacyanocobaltate

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presence of the excess cyanide. Pentacyanocobaltate forms within seconds. When prepared using a quaternary ammonium (quat) cyanide, crystals can be obtained...

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Morpheridine

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by any person) the following: (A) Anthranilic acid and its salts (B) Benzyl cyanide (C) Ephedrine, its salts, optical isomers, and salts of optical isomers...

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case, the cyanide anion is the synthetic equivalent for the COOH− synthon, while benzyl bromide is the synthetic equivalent for the benzyl synthon. The...

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