645-59-0

Basic information

• Product Name: 3-PHENYLPROPIONITRILE
• Synonyms: (2-Cyanoethyl)benzene;3-Phenylpropanenitrile;3-Phenylpropiononitrile;benzenepropanenitrile;Benzenepropionitrile;beta-Phenylethyl cyanide;Hydrocinnamique nitrile;hydrocinnamiquenitrile
• CAS NO: 645-59-0
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 211-447-8
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 645-59-0.mol
• Article Data: 306

Chemical Properties

• Melting Point: −2-−1 °C(lit.)
• Boiling Point: 113 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.001 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 1.68g/l (calculated)
• BRN: 636348
• CAS DataBase Reference: 3-PHENYLPROPIONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLPROPIONITRILE(645-59-0)
• EPA Substance Registry System: 3-PHENYLPROPIONITRILE(645-59-0)

Safety Data

• Hazard Codes: T,C
• Statements: 23/24/25-36-34
• Safety Statements: 36/37/39-45-27-26
• RIDADR: UN 3276 6.1/PG 3
• WGK Germany: 3
• RTECS: MW5604750
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 645-59-0(Hazardous Substances Data)

Usage

Description

3-Phenylpropionitrile is an organic compound with the chemical formula C9H7N. It is a derivative of propionitrile, featuring a phenyl group attached to the third carbon atom. 3-PHENYLPROPIONITRILE is known for its potential applications in various fields, particularly in the synthesis of pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
3-Phenylpropionitrile is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
3-Phenylpropionitrile is used as a precursor in the production of agrochemicals, specifically as a glucosinolate enzymic hydrolysis product with potential antibacterial activities against plant pathogenic bacteria. This application helps in the development of more effective and targeted pesticides to protect crops from diseases.
Used in Enzyme Research:
3-Phenylpropionitrile has been utilized in studies to investigate the free enzyme activity of nitrilase AtNIT1. This research contributes to the understanding of enzyme mechanisms and their potential applications in various industries, including pharmaceuticals and biotechnology.

Preparation

To a stirred solution of 3-phenylpropanamide (50 mg, 0.34 mmol) in acetonitrile (0.8 mL) at room temperature were successively added formic acid (0.2 mL) and paraformaldehyde (50 mg, 1.67 mmol). The reaction mixture was then refluxed for 12 h, and the solution obtained was cooled to room temperature. Work-up A: The crude mixture was concentrated under reduced pressure, and the residue was subjected to flash chromatography on silica gel (230–240 mesh) eluting with hexane/ethyl acetate (7:3) to yield 3-phenylpropanonitrile (37 mg, 85%). Work-up B: The reaction mixture was diluted with ethyl acetate (10 mL) and washed successively with saturated sodium hydrogen carbonate solution (5 mL) and water (5 mL). The combined aqueous layers were extracted with ethyl acetate (2 × 10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude 3-phenylpropanonitrile was purified as described above (Work-up A).

Synthesis Reference(s)

Journal of the American Chemical Society, 98, p. 4685, 1976 DOI: 10.1021/ja00431a078Chemical and Pharmaceutical Bulletin, 10, p. 427, 1962 DOI: 10.1248/cpb.10.427

InChI:InChI=1/C9H9N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7H2

Upstream product

• 4360-47-8 cinnamonitrile 
• 1197-50-8 3-phenylpropanal oxime 
• 151-50-8 potassium cyanide 
• 103-63-9 1-phenyl-2-bromoethane 
• 5331-42-0 2-cyano-3-phenylpropionic acid 
• 501-52-0 3-Phenylpropionic acid 
• 542-76-7 3-Chloropropionitrile 
• 71-43-2 benzene 
• 20496-01-9 4-chloro-n-butyric anhydride 
• 1885-38-7 cinnamic nitrile 
• 24225-08-9 methanesulfonyl cyanide 
• 114050-31-6 3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 61540-40-7 Dimethyl-dithiocarbamic acid 1-cyano-2-phenyl-ethyl ester 
• 935-02-4 3-Phenyl-2-propynonitrile 

Downstream Products

• 53174-17-7 (tert-Butyl-dimethyl-silanyl)-[2-(tert-butyl-dimethyl-silanyl)-3-phenyl-propenylidene]-amine 
• 65680-20-8 phenylpropionic acid thioamide 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 54321-42-5 2-benzylhexanenitrile 
• 53244-17-0 2-Cyclopentyl-3-phenyl-propionitrile 
• 76528-03-5 4-Isopropylidene-2,2-dimethyl-5-phenethyl-3,4-dihydro-2H-pyrrole 
• 76528-02-4 2,2,4,4-Tetramethyl-2,3,3a,4,9,10-hexahydro-1-aza-benzo[f]azulene 
• 52353-64-7 ethyl 3-phenylpropionimidate hydrochloride 
• 84831-51-6 2-acetyl-3-phenylpropanenitrile 
• 93340-37-5 3-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-2-phenethyl-benzonitrile 
• 66442-68-0 4-cyano-3,3,5-triphenylpyrazolenine 
• 497088-75-2 2-benzyl-3-oxopropanenitrile 
• 33802-51-6 α-methyl-β-phenylpropionitrile 
• 65-85-0 benzoic acid 

Relevant articles and documents

A Study of the Sodium Borohydride Reduction of α,β-Acetylenic vs α,β-Olefinic Nitriles

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Enantioselective hydrogenation of diaryl-substituted α,β-unsaturated nitriles

α,β-Unsaturated nitriles can be hydrogenated with enantioselectivities up to 88% ee using chiral ruthenium-diphenylphosphino bisaryl and bisheteroaryl complexes such as ruthenium(II)-BINAP and ruthenium(II)-BINP. Mechanistic investigations indicate that conversion is accelerated by electron-rich ligands and that an additional coordinative group needs be present in order to promote conversion. The chiral products are useful building blocks for the synthesis of histamine H2 agonists of the arpromidine type.

From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water

The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).

Method for dehydrating primary amide into nitriles under catalysis of cobalt

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.