Benzyl cyanide

From Sciencemadness Wiki
Revision as of 18:34, 29 December 2020 by Mabus (Talk | contribs)

(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Jump to: navigation, search
Not to be confused with benzonitrile.
Benzyl cyanide
Names
IUPAC name
Phenylacetonitrile
Other names
2-Phenylacetonitrile
Benzeneacetonitrile
Benzylnitrile
Benzyl nitrile
Phenylacetonitrile
α-Tolunitrile
Properties
C8H7N
C6H5CH2CN
Molar mass 117.15 g/mol
Appearance Colorless oily liquid
Odor Aromatic
Density 1.020 g/cm3 (20 °C)
Melting point −24 °C (−11 °F; 249 K)
Boiling point 233.5 °C (452.3 °F; 506.6 K)
0.1 g/100 ml
Solubility Miscible with acetone, diethyl ether, ethanol, isopropanol, methanol, THF
Vapor pressure 0.1 mmHg (20 °C)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 102 °C (215.6 °F; 375 K)
Lethal dose or concentration (LD, LC):
270 mg/kg (rat, oral)
Related compounds
Related compounds
Benzonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzyl cyanide (abbreviated BnCN) is an organic aromatic compound with the formula C6H5CH2CN.

Properties

Chemical

Hydrolysis of benzyl cyanide gives phenylacetic acid. Sulfuric acid is often used as catalyst, usually as 70% concentration.[1][2]

Physical

Benzyl cyanide is a colorless liquid, immiscible with water, but miscible with other organic solvents.

Availability

Benzyl cyanide is sold by chemical suppliers. Since it's classified as List I drug precursor in most countries, it's almost impossible to be acquired by the hobby chemist without a permit. In the United States it is classified as a DEA List I chemical.

Preparation

Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide.

C6H5CH2Cl + NaCN → C6H5CH2CN + NaCl

Oxidative decarboxylation of phenylalanine is another possible route.

Projects

  • Synthesis of various pharmaceuticals
  • Preparation of phenylacetic acid
  • Preparation of phenethylamine

Handling

Safety

Benzyl cyanide is irritant, though it's not very volatile. It has medium toxicity.

Storage

In closed bottles, away from light and air.

Disposal

Can be mixed with a more flammable solvent and burned.

References

  1. Perfumery Essent. Oil Record 14, 336 (1924)
  2. https://erowid.org/archive/rhodium/chemistry/phenylacetic.html

Relevant Sciencemadness threads