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Benzeneacetonitrile

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  • Benzeneacetonitrile (abbreviated BnCN) is a colorless, oily liquid with an aromatic odor.This colorless oily aromatic liquid i....
  • Nov 22,2019
Benzeneacetonitrile Basic information
Product Name:Benzeneacetonitrile
Synonyms:LABOTEST-BB LT00891699;BENZYL CYANIDE;benzeneacetonitrile;A-TOLUNITRILE;ALPHA-CYANOTOLUENE;phenyl acetyl nitrile;PHENYLACETONITRILE;TOLUNITRILE
CAS:140-29-4
MF:C8H7N
MW:117.15
EINECS:205-410-5
Product Categories:Agrochemical;Organics;Pharmaceutical Intermediates
Mol File:140-29-4.mol
Benzeneacetonitrile Structure
Benzeneacetonitrile Chemical Properties
Melting point −24 °C(lit.)
Boiling point 233-234 °C(lit.)
density 1.015 g/mL at 25 °C(lit.)
vapor pressure 0.1 mm Hg ( 20 °C)
refractive index n20/D 1.524
Fp 215 °F
storage temp. Store below +30°C.
solubility 0.1g/l
form Liquid
color Oily liquid
Odoraromatic odor
Water Solubility insoluble. <0.1 g/100 mL at 17 ºC
Merck 14,1131
BRN 385941
Stability:Stable. Incompatible with strong oxidizing agents. May produce hydrogen cyanide in a fire.
CAS DataBase Reference140-29-4(CAS DataBase Reference)
NIST Chemistry ReferenceBenzeneacetonitrile(140-29-4)
EPA Substance Registry SystemBenzeneacetonitrile (140-29-4)
Safety Information
Hazard Codes T+,T
Risk Statements 22-24-26-23/24/25
Safety Statements 28-36/37-45-23
RIDADR UN 2470 6.1/PG 3
WGK Germany 3
RTECS AM1400000
8-9
Autoignition Temperature590 °C
Hazard Note Very Toxic
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29269090
Hazardous Substances Data140-29-4(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 270 mg/kg LD50 dermal Rabbit 270 mg/kg
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Benzeneacetonitrile Usage And Synthesis
Chemical Propertiescolourless liquid
Chemical PropertiesBenzyl cyanide is a colorless, oily liquid with an aromatic odor.
UsesOrganic synthesis, especially penicillin precursors.
UsesPhenylacetonitrile is used in organic synthesis for dyes, perfumes, pharmaceuticals, especially penicillin precursors. It is also used as a solvent.
Production MethodsBenzyl 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 ).
DefinitionChEBI: 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 DescriptionA 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 ReactionsBenzeneacetonitrile is moisture sensitive. Insoluble in water.
Reactivity ProfilePHENYLACETONITRILE can react with strong acids, strong bases, strong oxidizing agents and strong reducing agents. Benzeneacetonitrile may react vigorously with sodium hypochlorite. .
HazardHighly toxic, absorbed by skin.
Health HazardBenzyl 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 HazardPoisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.
Fire HazardWhen 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 usesBenzyl 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 ProfilePoison 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.
MetabolismGiacosa 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.
ShippingUN2470 Phenylacetonitrile, Hazard Class: 6.1; Labels: 6.1—Poisonous materials.
Purification MethodsAny 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.]
IncompatibilitiesViolent 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.
Tag:Benzeneacetonitrile(140-29-4) Related Product Information
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