phenyl acetonitrile
acetonitrile, phenyl-
Identification
| Name | phenyl acetonitrile |
| IUPAC | 2-phenylacetonitrile |
| CAS Number | 140-29-4 |
| EINECS | 205-410-5 |
| FDA UNII | 23G40PRP93 |
| Molecular Formula | C8 H7 N |
| Molecular Weight | 117.15079000 |
| MDL Number | MFCD00001894 |
| Nikkaji Number | J5.653G |
| Beilstein | 0385941 |
| XlogP3 | 1.60 (est) |
Regulatory
Physical Properties
| Assay | 97.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | -24.00 °C. @ 760.00 mm Hg |
| Boiling Point | 233.00 to 234.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.056000 mmHg @ 25.00 °C. (est) |
| Flash Point | 215.00 °F. TCC ( 101.67 °C. ) |
| logP (o/w) | 1.560 |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | fragrance |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-guinea pig LD50 10 mg/kg |
| Dermal Toxicity | skin-guinea pig LDLo 5 ml/kg |
| Inhalation Toxicity | inhalation-mouse LC50 100 mg/m3/2H |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'LUNGS, THORAX, OR RESPIRATION: DYSPNEA\nBEHAVIORAL: ATAXIA\nPERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE', 'BEHAVIORAL: ATAXIA\nPERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE\nLUNGS, THORAX, OR RESPIRATION: DYSPNEA', 'BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)\nBEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)\nLUNGS, THORAX, OR RESPIRATION: DYSPNEA']
Safety in Use
| Category | natural substances and extractives |
| IFRA Critical Effect | Release of cyanide |
| IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%) | Category 1: Products applied to the lips |
| Notes | IFRA FLAVOR REQUIREMENTS: |
| Recommendation for phenyl acetonitrile flavor usage levels up to | not for flavor use. |
Lluch Essence S.L.
A family company dedicated to sales and distribution
Flexibility, availability, price and quality.
Potential Uses
Natural Occurrence
Synonyms
acetonitrile, phenyl-
benzene acetonitrile
benzeneacetonitrile
benzyl cyanide
benzyl nitrile
benzylcyanide
cyanomethyl benzene
cyanomethyl)benzene
cyanomethylbenzene
a-
cyanotoluene
phenyl acetyl nitrile
phenylacetonitrile
2-
phenylacetonitrile
2-
phenylethanenitrile
a-
tolunitrile
PubMed:
Biotransformation of phenylacetonitrile to 2-hydroxyphenylacetic acid by marine fungi.
PubMed:
Herbivore-induced phenylacetonitrile is biosynthesized from de novo-synthesized L-phenylalanine in the giant knotweed, Fallopia sachalinensis.
PubMed:
Mass spectral determination of phenylacetonitrile (PAN) levels in body tissues of adult desert locust, Schistocerca gregaria.
PubMed:
Synthesis of 3-cyanoindole derivatives mediated by copper(I) iodide using benzyl cyanide.
PubMed:
Study of the lithiated phenylacetonitrile monoanions and dianions formed according to the lithiated base used (LHMDS, LDA, or n-BuLi). 2. Alkylation and deuteriation mechanism study by vibrational and NMR spectroscopy and quantum chemistry calculations.
PubMed:
Phenylacetonitrile from the giant knotweed, Fallopia sachalinensis, infested by the Japanese beetle, Popillia japonica, is induced by exogenous methyl jasmonate.
PubMed:
A new synthetic route to 3-oxo-4-amino-1,2,3-oxadiazole from the diazeniumdiolation of benzyl cyanide: stable sydnone iminium N-oxides.
PubMed:
An organic molecule modulated chemoselective cyclization of alkynyl nitriles tethered to 2-alkyl substituted chromones with multireactive sites.
PubMed:
Wings and legs are production sites for the desert locust courtship-inhibition pheromone, phenylacetonitrile.
PubMed:
2-Methyl-3-nitro-benzyl cyanide.
PubMed:
Identification of the monoanions and of their complexes with lithium salts possibly formed in solution during the alkylation of lithiated phenylacetonitrile dianions: infrared spectroscopy and density functional theory calculations.
PubMed:
E/Z oxime isomerism in PhC(NOH)CN.
PubMed:
An assessment of the release of inorganic cyanide from the fragrance materials benzyl cyanide, geranyl nitrile and citronellyl nitrile applied dermally to the rat.
PubMed:
Urinary thiocyanate levels as a biomarker for the generation of inorganic cyanide from benzyl cyanide in the rat.
PubMed:
Solvent-free condensation of phenylacetonitrile and nonanenitrile with 4-methoxybenzaldehyde: optimization and mechanistic studies.
PubMed:
Toxicity of benzyl cyanide in the rat.
PubMed:
Sonocatalyzed synthesis of 2-phenylvaleronitrile under controlled reaction conditions--a kinetic study.
PubMed:
Activation of nitriles by metal ligand cooperation. Reversible formation of ketimido- and enamido-rhenium PNP pincer complexes and relevance to catalytic design.
PubMed:
An unusual presentation of a customs importation seizure containing amphetamine, possibly synthesized by the APAAN-P2P-Leuckart route.
PubMed:
Effects of ultrasound on the formation of alpha-benzoylbenzyl cyanide from benzyl cyanide and alkylphenyl ketone from alpha-alkylbenzyl cyanide by potassium superoxide in the presence of crown ether.
PubMed:
Ultrasound promoted C-alkylation of benzyl cyanide--effect of reactor and ultrasound parameters.
PubMed:
Structural and vibrational characterization of the mono and dilithiated species derived from phenylacetonitrile in THF by infrared and Raman spectroscopy and density functional theory calculations.
PubMed:
Identification of pheromone-like compounds in male reproductive organs of the oriental locust Locusta migratoria.
PubMed:
Insect egg deposition induces indirect defense and epicuticular wax changes in Arabidopsis thaliana.
PubMed:
Substituted alpha-(phenylhydrazono)phenylacetonitrile derivatives. Part 1: A new class of uncoupler of oxidative phosphorylation.
PubMed:
Effective computational modeling of constitutional isomerism and aggregation states of explicit solvates of lithiated phenylacetonitrile.
PubMed:
Influence of ultrasound power on the alkylation of phenylacetonitrile under solid-liquid phase transfer catalysis conditions.
PubMed:
[Alkylation of benzyl cyanide].
PubMed:
Novel phenoxyalkylamine derivatives. IV. Synthesis, Ca2+-antagonistic activity and quantitative structure-activity analysis of alpha-isopropyl-alpha-[3-[3-(3-methoxyphenoxy)propylamino]propyl]- alpha-phenylacetonitrile derivatives.
PubMed:
Novel phenoxyalkylamine derivatives. V. Synthesis, alpha-blocking activity and quantitative structure-activity analysis of alpha-[(phenoxyethylamino)propyl]-alpha-phenylacetonitrile derivatives.
PubMed:
[Biotransformation and pharmacokinetics of (3,4-dichloroanilino)phenylacetonitrile (H 74)].
PubMed:
[Synthesis of aminoalkyl derivatives of phenylacetonitrile from the bromonitriles].
PubMed:
C-alkylation of active methylene compounds by means of alcohol. IV. C-alkylation of phenylacetonitrile with aliphatic alcohols.
PubMed:
Antiarrhythmic action of alpha-isopropyl-beta-dimethylaminopropyl-phenylacetonitrile (Perocan).
PubMed:
[Respiratory physiological studies before and after the administration of alpha-(isopropyl)-beta-(2-dimethylaminopropyl)-phenylacetonitrile].
PubMed:
[On substantiation of the maximum permissible concentration of benzyl cyanide in the air of work sites].
PubMed:
Substituted alpha-(phenylhydrazono)phenylacetonitrile derivatives. Part 2: Synthesis and biological activity of pro-pesticides.
PubMed:
Study of the lithiated phenylacetonitrile monoanions and dianions formed according to the lithiated base used (LHMDS, LDA, or n-BuLi). 1. Evidence of heterodimer ("Quadac") or dianion formation by vibrational spectroscopy.
PubMed:
[Novel phenoxyalkylamine derivatives. VI. Synthesis and alpha-blocking activity of alpha-[(phenoxyethylamino)propyl]-alpha-phenylacetonitrile derivatives].
PubMed:
[Spasmolytic activity of (3,4-dichloroanilino)phenylacetonitrile (H 74) and its analogs].
PubMed:
C- and N-acetylation of phenylacetamide with acetic anhydride by boron trifluoride. Conversion of phenylacetonitrile to diacetyl derivative of phenylacetamide.
PubMed:
[The use of alpha-isopropyl-alpha-(beta-dimethylaminopropyl)-phenylacetonitrile citrate as an antitussive drug].
PubMed:
[Pharmacology of 2-isopropyl-2-(2-dimethylaminopropyl)-2-phenylacetonitrile citrate].
PubMed:
Isolation of identical nitrilase genes from multiple bacterial strains and real-time PCR detection of the genes from soils provides evidence of horizontal gene transfer.
PubMed:
Biosynthesis of terephthalic acid, isophthalic acid and their derivatives from the corresponding dinitriles by tetrachloroterephthalonitrile-induced Rhodococcus sp.
PubMed:
Nitrile imines and nitrile ylides: rearrangements of benzonitrile N-methylimine and benzonitrile dimethylmethylide to azabutadienes, carbodiimides, and ketenimines. Chemical activation in thermolysis of azirenes, tetrazoles, oxazolones, isoxazolones, and oxadiazolones.
PubMed:
Risk of egg parasitoid attraction depends on anti-aphrodisiac titre in the large cabbage white butterfly Pieris brassicae.
PubMed:
POP-pincer ruthenium complexes: d(6) counterparts of osmium d(4) species.
PubMed:
Isolation and characterization of a nitrile hydrolysing acidotolerant black yeast-Exophiala oligosperma R1.
PubMed:
Biotransformation of methylphenylacetonitriles by Brazilian marine fungal strain Aspergillus sydowii CBMAI 934: eco-friendly reactions.
PubMed:
Nucleophilic attack of α-aminoalkyl radicals on carbon-nitrogen triple bonds to construct α-amino nitriles: an experimental and computational study.
PubMed:
Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents.
PubMed:
Purification and characterization of heterologously expressed nitrilases from filamentous fungi.
PubMed:
Progress in carbonylative [2+2+1] cycloaddition: utilization of a nitrile group as the Ï component.
PubMed:
Utilization of arylaliphatic nitriles by haloalkaliphilic Halomonas nitrilicus sp. nov. isolated from soda soils.
PubMed:
Versatile Reactivity of Scorpionate-Anchored YttriumDialkyl Complexes towards Unsaturated Substrates.
PubMed:
Reactions of Groupâ
4 metallocene complexes with mono- and diphenylacetonitrile: formation of unusual four- and six-membered metallacycles.
PubMed:
Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions.
PubMed:
Nickel-catalyzed decyanation of inert carbon-cyano bonds.
PubMed:
Volatiles from apple trees infested with light brown apple moth larvae attract the parasitoid Dolichogenidia tasmanica.
PubMed:
A new nitrilase from Bradyrhizobium japonicum USDA 110. Gene cloning, biochemical characterization and substrate specificity.
PubMed:
Aerobic oxidations of C60(2-) in the presence of PhCN and PhCH2CN: oxygenation versus dehydrogenation reactions.
PubMed:
Present or past herbivory: a screening of volatiles released from Brassica rapa under caterpillar attacks as attractants for the solitary parasitoid, Cotesia vestalis.
PubMed:
Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity.
PubMed:
Photostimulated reduction of nitriles by SmI2.
PubMed:
Concentration-dependent parsimonious releaser roles of gregarious male pheromone of the desert locust, Schistocerca gregaria.
PubMed:
Synthesis and characterization of novel 2, 2'-bipyrimidine fluorescent derivative for protein binding.
PubMed:
Investigation of photodegradation and hydrolysis of selected substituted urea and organophosphate pesticides in water.
PubMed:
Phenology of semiochemical-mediated host foraging by the western boxelder bug, Boisea rubrolineata, an aposematic seed predator.
PubMed:
Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases.
PubMed:
[Design, synthesis and evaluation of novel 2H-1, 4-benzodiazepine-2-ones as inhibitors of HIV-1 transcription].
PubMed:
Differential response in foliar chemistry of three ash species to emerald ash borer adult feeding.
PubMed:
Mechanical activation of catalysts for C-C bond forming and anionic polymerization reactions from a single macromolecular reagent.
PubMed:
Hitch-hiking parasitic wasp learns to exploit butterfly antiaphrodisiac.
PubMed:
Genome mining for the discovery of new nitrilases in filamentous fungi.
PubMed:
Volatile composition screening of Salix spp. nectar honey: benzenecarboxylic acids, norisoprenoids, terpenes, and others.
PubMed:
Stereodivergent quaternization of 2-alkyl-2-p-tolylsulfinylacetonitriles: NMR spectroscopic evidence of planar and pyramidal benzylic carbanions.
PubMed:
Novel cross-stage solitarising effect of gregarious-phase adult desert locust (Schistocerca gregaria (Forskål)) pheromone on hoppers.
PubMed:
Biocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401.
PubMed:
Metalated nitrile and enolate chlorinations.
PubMed:
Chemical ecology of obligate pollination mutualisms: testing the 'private channel' hypothesis in the Breynia-Epicephala association.
PubMed:
Odorous products of the chlorination of phenylalanine in water: formation, evolution, and quantification.
PubMed:
In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products.
PubMed:
Juvenile-hormone-mediated plasticity of aggregation behaviour and olfactory processing in adult desert locusts.
PubMed:
Anti-aphrodisiac compounds of male butterflies increase the risk of egg parasitoid attack by inducing plant synomone production.
PubMed:
Isocyanides inhibit human heme oxygenases at the verdoheme stage.
PubMed:
Alternate substrates of dopamine beta-hydroxylase. I. Kinetic investigations of benzyl cyanides as substrates and inhibitors.
PubMed:
Characterisation of the substrate specificity of the nitrile hydrolyzing system of the acidotolerant black yeast Exophiala oligosperma R1.
PubMed:
Rhodium-catalyzed reductive cleavage of carbon-cyano bonds with hydrosilane: a catalytic protocol for removal of cyano groups.
PubMed:
Reductions of aliphatic and aromatic nitriles to primary amines with diisopropylaminoborane.
PubMed:
Metabolism of organonitriles to cyanide by rat nasal tissue enzymes.
PubMed:
Nucleophilicities of the anions of arylacetonitriles and arylpropionitriles in dimethyl sulfoxide.
PubMed:
Chemical composition, allelopatic and cytotoxic effects of essential oils of flowering tops and leaves of Crambe orientalis L. from Iran.
PubMed:
Dolichodial: a new aphid sex pheromone component?
PubMed:
Structure of a mutagen from roasted seeds of Moringa oleifera.
PubMed:
Male-derived butterfly anti-aphrodisiac mediates induced indirect plant defense.
PubMed:
Comparison of the volatile composition in thyme honeys from several origins in Greece.
PubMed:
A comprehensive investigation of the chemistry and basicity of a parent amidoruthenium complex.
PubMed:
Aggregation pheromone system of adult gregarious desert locust schistocerca gregaria (forskal).
PubMed:
Stereoselective construction of nitrile-substituted cyclopropanes.
PubMed:
Purification and characterization of an enantioselective arylacetonitrilase from Pseudomonas putida.
PubMed:
Derivative of alpha,beta-dicyanostilbene: convenient precursor for the synthesis of diphenylmaleimide compounds, E-Z isomerization, crystal structure, and solid-state fluorescence.
PubMed:
Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya.
PubMed:
Genetic change may be caused by interference with protein-protein interactions.
PubMed:
Stereoselective quaternization of alpha-amino phenylacetonitriles mediated by a remote sulfinyl group.
PubMed:
Chemical communication: butterfly anti-aphrodisiac lures parasitic wasps.
PubMed:
Improved reagent for electrophilic amination of stabilized carbanions.
PubMed:
Antiaphrodisiacs in pierid butterflies: a theme with variation!
PubMed:
Antennal perception of oilseed rape,Brassica napus (Brassicaceae), volatiles by the cabbage seed weevilCeutorhynchus assimilis (Coleoptera, Curculionidae).
PubMed:
Mammalian pheromones VIII Chemical characterization of preorbital gland secretion of grey duiker,Sylvicapra grimmia (Artiodactyla: Bovidae).
PubMed:
Characterization of benzyl isothiocyanate and phenyl acetonitrile from papayas by mass spectrometry.
PubMed:
Synthesis and antiprotozoal evaluation of benzothiazolopyrroloquinoxalinones, analogues of kuanoniamine A.
PubMed:
The physiology of locust phase polymorphism: an update.
PubMed:
Courtship inhibition pheromone in desert locusts, Schistocerca gregaria.
PubMed:
Flash vacuum pyrolysis over solid catalysts. 2. pyrazoles over hydrotalcites.
PubMed:
Novel heme-containing lyase, phenylacetaldoxime dehydratase from Bacillus sp. strain OxB-1: purification, characterization, and molecular cloning of the gene.
PubMed:
Biodegradation of cyanide compounds by a Pseudomonas species (S1).
PubMed:
Fecal volatiles as part of the aggregation pheromone complex of the desert locust,Schistocerca gregaria (Forskal) (Orthoptera: Acrididae).
PubMed:
Mechanistic and structural studies on Rhodococcus ATCC 39484 nitrilase.
PubMed:
Regiochemistry and substrate stereoselectivity of O-demethylation of verapamil in the presence of the microsomal fraction from rat and human liver.
PubMed:
Constituents of mandibular and Dufour's glands of an australianPolyrhachis weaver ant.
PubMed:
Ozone degrades common herbivore-induced plant volatiles: does this affect herbivore prey location by predators and parasitoids?
PubMed:
Benzyl isothiocyanate is the chief or sole anthelmintic in papaya seed extracts.
PubMed:
Boundary conditions on the partitioning of deaminatively generated benzyl cations.
PubMed:
Induction by nitriles of sex chromosome aneuploidy: tests of mechanism.
PubMed:
A kinetic evaluation of monoamine oxidase activity in rat liver mitochondrial outer membranes.
PubMed:
The reaction pathway of membrane-bound rat liver mitochondrial monoamine oxidase.
PubMed:
Naturally occurring toxic factors in plants and animals used as food.
PubMed:
A novel azaindolizinone derivative ZSET1446 (spiro[imidazo[1,2-a]pyridine-3,2-indan]-2(3H)-one) improves methamphetamine-induced impairment of recognition memory in mice by activating extracellular signal-regulated kinase 1/2.
PubMed:
Glycine conjugates in a lepidopteran insect herbivore--the metabolism of benzylglucosinolate in the cabbage white butterfly, Pieris rapae.
PubMed:
Retentivity and enantioselectivity of uniformly-sized molecularly imprinted polymers for (S)-nilvadipine in aqueous and non-aqueous mobile phases.
PubMed:
Regulation of aldoxime dehydratase activity by redox-dependent change in the coordination structure of the aldoxime-heme complex.
PubMed:
A ruthenium-grafted hydrotalcite as a multifunctional catalyst for direct alpha-alkylation of nitriles with primary alcohols.
PubMed:
Effects of juvenile hormone treatment on phase changes and pheromone production in the desert locust, Schistocerca gregaria (Forskal) (Orthoptera: Acrididae).
PubMed:
Cyanogenesis in glucosinolate-producing plants: Carica papaya and Carica quercifolia.
PubMed:
Selective mono-C-methylations of arylacetonitriles and arylacetates with dimethylcarbonate: a mechanistic investigation.
PubMed:
Kairomone from dandelion,Taraxacum officinale, attractant for scarab beetleAnomala octiescostata.
PubMed:
Cytochrome P-455 nm complex formation in the metabolism of phenylalkylamines. XIII. Enzyme interactions with a series of beta-alkyl-substituted 2-phenylethanamines and corresponding N-hydroxylamines.
PubMed:
Nitriles and isonitriles as interferents in cyanide determination in polluted waters.
PubMed:
Mutagens from roasted seeds of Moringa oleifera.
PubMed:
Biological properties of 3-benzyl-1,2-benzisothiazole compounds.
PubMed:
A comparative randomized double-blind clinical trial of isoaminile citrate and chlophedianol hydrochloride as antitussive agents.
PubMed:
The biosynthesis of cyanogenic glucosides in higher plants. Channeling of intermediates in dhurrin biosynthesis by a microsomal system from Sorghum bicolor (linn) Moench.
PubMed:
Analgesic activity of the epimeric tropane analogs of meperidine. A physical and pharmacological study.
PubMed:
A cyanogenic glycoside from Canthium schimperianum.