phenyl acetonitrile

acetonitrile, phenyl-

CAS: 140-29-4 C8 H7 N MW: 117.15079000

Identification

Namephenyl acetonitrile
IUPAC2-phenylacetonitrile
CAS Number140-29-4
EINECS205-410-5
FDA UNII23G40PRP93
Molecular FormulaC8 H7 N
Molecular Weight117.15079000
MDL NumberMFCD00001894
Nikkaji NumberJ5.653G
Beilstein0385941
XlogP31.60 (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

CosIngcosmetic data
Cosmetic Usesfragrance

No sensory data available

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-guinea pig LD50 10 mg/kg
Dermal Toxicityskin-guinea pig LDLo 5 ml/kg
Inhalation Toxicityinhalation-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

Categorynatural substances and extractives
IFRA Critical EffectRelease of cyanide
IFRA RESTRICTION LIMITS IN THE FINISHED PRODUCT (%)Category 1: Products applied to the lips
NotesIFRA FLAVOR REQUIREMENTS:
Recommendation for phenyl acetonitrile flavor usage levels up tonot for flavor use.

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Potential Uses

FL cabbage FL cauliflower FL chocolate cocoa FL onion FR papaya FR peanut FL tea FL tomato trassi

Natural Occurrence

allamanda cathartica linn. flower oil brazil @ 9.40% Data champaca absolute @ 1.30% Data champaca concrete @ 1.20% Data couroupita guianensis aubl. flower oil brazil @ 0.60% Data cress garden cress plant hyacinthus orientalis absolute @ 0.02-0.03% Data jasmin sambac absolute egypt @ 1.15% Data kohlrabi stem narcissus absolute (narcissus tazetta var. chinensis) @ 0.18% Data neroli oil CO2 extract @ 0.67% Data orangeflower absolute morocco @ 0.0-1.1% Data orangeflower water absolute @ 0.8-5.0% Data papaya fruit peppermint leaf tomato fruit ylang ylang oil @ 0.14% Data ylang ylang oil CO2 extract @ 0.09% Data

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 π 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 Group 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.