Phenylacetonitrile

Base Information

• Chemical Name: Phenylacetonitrile
• CAS No.: 140-29-4
• Molecular Formula: C8H7N
• Molecular Weight: 117.15
• Hs Code.: 2837.19 Oral rat LD50: 270 mg/kg
• European Community (EC) Number: 205-410-5
• NSC Number: 118418,3407
• UN Number: 2470
• UNII: 23G40PRP93
• DSSTox Substance ID: DTXSID2021492
• Nikkaji Number: J5.653G
• Wikipedia: Benzyl_cyanide
• Wikidata: Q425620
• Metabolomics Workbench ID: 46397
• ChEMBL ID: CHEMBL3560735
• Mol file: 140-29-4.mol

Synonyms:benzyl cyanide;phenylacetonitrile

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Chemical Property of Phenylacetonitrile

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.1 mm Hg ( 20 °C)
• Melting Point: -24 °C(lit.)
• Refractive Index: 1.523
• Boiling Point: 233.499 °C at 760 mmHg
• Flash Point: 101.667 °C
• PSA: 23.79000
• Density: 1.013 g/cm³
• LogP: 1.75268
• Storage Temp.: Store below +30°C.
• Solubility.: 0.1g/l
• Water Solubility.: insoluble.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 117.057849228
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

Safty Information:

• Pictogram(s): T+,T
• Hazard Codes: T+,T
• Statements: 22-24-26-23/24/25
• Safety Statements: 28-36/37-45-23

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC=C(C=C1)CC#N
• Uses: Organic synthesis, especially penicillin precursors. Phenylacetonitrile is used in organic synthesis for dyes, perfumes, pharmaceuticals, especially penicillin precursors. It is also used as a solvent.

Technology Process of Phenylacetonitrile

There total 431 articles about Phenylacetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

C21H16N2O4 → phenylacetonitrile (140-29-4) + biphenyl-4-carboxylic acid (92-92-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; Heating;

DOI:10.1016/0040-4039(96)01779-0

Reference yield: 88.0%

benzyl methoxymethyl ether (31600-55-2) + (1-methoxymethoxy)ethylbenzene (94073-86-6) + tetra-n-butylammonium cyanide (10442-39-4) → phenylacetonitrile (140-29-4) + 1-phenylethyl cyanide (1823-91-2)

Guidance literature:

With 1-(n-butyl)-3-methylimidazolium tetrachloroindate; at 135 - 140 ℃; for 0.075h; chemoselective reaction; Microwave irradiation; Neat (no solvent);

DOI:10.1016/j.tetlet.2010.04.056

Reference yield: 86.0%

benzyl chloride (100-44-7) + 2-phenylthioacetamide (645-54-5) → dibenzyl sulfide (538-74-9) + phenylacetonitrile (140-29-4)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In water; benzene; at 30 ℃; for 2h; Product distribution;

upstream raw materials:

phenylacetic acid

benzenesulfonamide

1,2-di(phenylacetyl)hydrazine

3-phenyl-propynoic acid amide

Downstream raw materials:

3-hexyl-5-phenyl-3H-[1,2,3]triazol-4-ylamine

2-benzyl-3-cyano-2-hydroxy-3-phenyl-propionic acid

3-(3-nitro-phenyl)-2-phenyl-acrylonitrile

(E)-2,3-diphenylacrylonitrile

Refernces

• 1、 Mizuno, Akira,Hamada, Yasumasa,Shioiri, Takayuki. "New Methods and Reagents in Organic Synthesis; 6. A Simple One-Pot Conversion of Primary Alcohols to Nitriles having One C-Atom more". . p. 1007 - 1009. Retrieved 1980.
• 2、 Takeuchi,Miwa,Okada. "Kinetic studies on the catalytic synthesis of benzyl cyanide from 2-phenylethanol and ammonia". . p. 2637 - 2641. Retrieved 1980.
• 3、 Doan, Tan L.H.,Le, Thach N.. "Switch of reaction pathway induced by solid support and ultrasound". . p. 337 - 340. Retrieved 2012.
• 4、 Uno, Hidemitsu,Fujiki, Satomi,Suzuki, Hitomi. "A New Synthesis of α-Phenylhomoallylnitriles from β-Nitrostyrene and Allylic Silanes". . p. 1267 - 1268. Retrieved 1986.
• 5、 Glass et al.. "-". . p. 1546. Retrieved 1971.
• 6、 Isomura et al.. "-". . p. 3499. Retrieved 1968.
• 7、 Bartmess et al.. "". . p. 6046,6049,6053. Retrieved 1979.
• 8、 Hasapis, Xenophon,MacLeod, Alexander J.. "BENZYLGLUCOSINOLATE DEGRADATION IN HEAT-TREATED LEPIDIUM SATIVUM SEEDS AND DETECTION OF A THIOCYANATE-FORMING FACTOR". . p. 1009 - 1014. Retrieved 1982.
• 9、 Clark, James H.,Duke, Catherine V. A.. "Supported Cyanides: The Interaction of Potassium Cyanide with High Surface Area Inorganic Support Materials and the Development of Highly Reactive Cyanide Reagents". . p. 1330 - 1332. Retrieved 1985.
• 10、 Kirschning, Andreas,Altwicker, Carsten,Drger, Gerald,Harders, Jan,Hoffmann, Nora,Hoffmann, Ulrich,Schnfeld, Hagen,Solodenko, Wladimir,Kunz, Ulrich. "Passflow syntheses using functionalized monolithic polymer/glass composites in flow-through microreactors". . p. 3995 - 3998. Retrieved 2001.