| Chemical Properties | colourless liquid |
| Chemical Properties | Benzyl cyanide is a colorless, oily liquid with
an aromatic odor. |
| Uses | Organic synthesis, especially penicillin precursors. |
| Uses | Phenylacetonitrile is used in organic synthesis for dyes, perfumes, pharmaceuticals, especially penicillin precursors. It is also used as a solvent. |
| Production Methods | Benzyl cyanide is synthesized by reaction of benzyl chloride with potassium
cyanide or sodium cyanide . The nitrile is a natural constituent of
plants and is a constituent of foods, particularly citrus fruits, papaya, cabbage,
mushrooms, roasted onions, tomatoes, cocoa, tea, roasted peanuts and cauliflower
.The benzyl cyanide, at least in part, is formed by breakdown of
benzylglucosinolate in the plant material. Benzyl
nitrile also is found in tap water, river water, sewage and in
cigarette smoke ). |
| Definition | ChEBI: A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a phenyl group. |
| Synthesis Reference(s) | Canadian Journal of Chemistry, 39, p. 1340, 1961 DOI: 10.1139/v61-169
Chemistry Letters, 13, p. 1511, 1984
Organic Syntheses, Coll. Vol. 1, p. 107, 1941 |
| General Description | A colorless oily liquid with an aromatic odor. Insoluble in water and slightly denser than water. Contact may irritate skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals. |
| Air & Water Reactions | Benzeneacetonitrile is moisture sensitive. Insoluble in water. |
| Reactivity Profile | PHENYLACETONITRILE can react with strong acids, strong bases, strong oxidizing agents and strong reducing agents. Benzeneacetonitrile may react vigorously with sodium hypochlorite. . |
| Hazard | Highly toxic, absorbed by skin. |
| Health Hazard | Benzyl cyanide is a highly toxic irritant that may be fatal if inhaled, swallowed or
absorbed through the skin. The chemical causes eye, mucous
membrane and skin irritation. Benzyl cyanide was applied as a 2% concentration
in petroleum to the skin of 27 human volunteers and found to be nonsensitizing. |
| Health Hazard | Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes. |
| Fire Hazard | When heated to decomposition, Benzeneacetonitrile emits very toxic fumes of cyanide and nitrogen oxides. Container may explode in heat of fire. Runoff from fire control water may give off poisonous gases. Avoid sodium hypochlorite. |
| Industrial uses | Benzyl cyanide is employed as a chemical intermediate for the synthesis of
amphetamine, phenobarbital and methyl phenidylacetate. It is also used for
perfumes and flavors and is, therefore, added to soaps, detergents, creams and
lotions. |
| Safety Profile | Poison by ingestion, inhalation, skin contact, subcutaneous, and intraperitoneal routes. A skin irritant. Explosive reaction with sodium hypochlorite. Used in production of drugs of abuse. When heated to decomposition it emits very toxic fumes of CNand NOx. See also NITRILES |
| Potential Exposure | (as CN): Benzyl cyanide is used in
organic synthesis, especially of penicillin precursors. It is
used as a chemical intermediate for amphetamines, phenobarbital;
the stimulant, methyl phenidylacetate; esters as
perfumes and flavors. |
| Metabolism | Giacosa isolated phenylaceturic acid from the urine of a dog dosed with
benzyl cyanide, while Adeline et al showed that in the dog, benzyl cyanide
formed both benzoic acid and a small amount of ethereal sulfate. In rabbits, a large
proportion of the cyano group could be accounted for as thiocyanate ion in the
urine. There was a sex difference in the conversion with
female rabbits excreting 70% of the dose as thiocyanate and males only 50%.
However, cyanide was liberated slowly from i.p. or orally administered benzyl
cyanide in rats and excreted in the urine as cyanide and thiocyanate, the proportion
of the former increasing with the dose .
Benzyl cyanide is oxidized by mouse liver microsomes to benzaldehyde and
cyanide ion presumably via the intermediate mandelonitrile.
The microsomal metabolism of benzyl cyanide and other nitriles was significantly
increased when mice were pre treated with ethanol ,
suggesting that the ethanol-inducible cytochrome P-450 may
play an important role in the metabolism of such compounds. |
| Shipping | UN2470 Phenylacetonitrile, Hazard Class: 6.1;
Labels: 6.1—Poisonous materials. |
| Purification Methods | Any benzyl isocyanide impurity can be removed by shaking vigorously with an equal volume of 50% H2SO4 at 60o, washing with saturated aqueous NaHCO3, then half-saturated NaCl solution, drying and fractionally distilling under reduced pressure. Distillation from CaH2 causes some decomposition of this compound: it is better to use P2O5. Other purification procedures include passage through a column of highly activated alumina, and distillation from Raney nickel. Precautions should be taken because of possible formation of free TOXIC cyanide, use an efficient fume cupboard.[Beilstein 9 IV 1663.] |
| Incompatibilities | Violent reaction with strong oxidizers;
sodium hypochlorite, lithium aluminum hydride. Nitriles
may polymerize in the presence of metals and some metal
compounds. They are incompatible with acids; mixing
nitriles with strong oxidizing acids can lead to extremely
violent reactions. Nitriles are generally incompatible with
other oxidizing agents such as peroxides and epoxides.
The combination of bases and nitriles can produce hydrogen
cyanide. Nitriles are hydrolyzed in both aqueous acid
and base to give carboxylic acids (or salts of carboxylic
acids). These reactions generate heat. Peroxides convert
nitriles to amides. Nitriles can react vigorously with
reducing agents. Acetonitrile and propionitrile are soluble
in water, but nitriles higher than propionitrile have low
aqueous solubility. They are also insoluble in aqueous
acids. |
