Synthesis of 3-phenylpropiolonitrile

Preparation of 3-phenylpropiolonitrile

Alternative Names: Phenylpropiolonitrile; 2-Propynenitrile, 3-phenyl-; 3-phenyl-2-propynenitrile; Cyanophenylacetylene;

Preparation of 3-phenylpropiolonitrile (Phenylpropiolonitrile; 2-Propynenitrile, 3-phenyl-; 3-phenyl-2-propynenitrile; Cyanophenylacetylene)

Preparation of 3-phenylpropiolonitrile (Phenylpropiolonitrile; 2-Propynenitrile, 3-phenyl-; 3-phenyl-2-propynenitrile; Cyanophenylacetylene)

A mixture of 1 equiv. of 3-phenylprop-2-ynal (phenylpropiolaldehyde) and 1.1 equiv. of hydroxylamine hydrochloride are mixed with the dimethylsulfoxide until the homogeneous mixture is obtained (3-5 volumes) and the obtained mixture is stirred at 70° C for 1-2 hours. The reaction is monitored by TLC (ethyl acetate:hexane 5:95) and when is completed the mixture is cooled and poured in water,  the reaction product is extracted with ether, dried and the ether is removed by evaporation affording 93% of the 3-phenylpropiolonitrile.

J. K. Augustine, et al. Synlett, 2223-2227, (2011) (supporting information)

IUPAC Name

3-phenylprop-2-ynenitrile

InChI

InChI=1S/C9H5N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H

InChI Key

IYXVSRXFGYDNEV-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C#CC#N

MeSH Synonyms

3-phenyl-2-propynenitrile

Depositor-Supplied Synonyms

3-Phenylpropiolonitrile, 935-02-4, Phenylpropiolonitrile, 2-Propynenitrile, 3-phenyl-, 3-phenyl-2-propynenitrile, Cyanophenylacetylene, Phenylpropynenitrile, Propiolonitrile, phenyl-, 3-phenylprop-2-ynenitrile, Phenylpropiolique nitrile [French], NSC 71547, BRN 0386022, AI3-11802, NSC71547, Phenyl-propynenitrile, Phenylpropiolique nitrile, AC1Q4QBA, AC1L3WC2, 3-phenyl-prop-2-ynenitrile, 2-Propynenitrile,3-phenyl-, NCIOpen2_000538, ACMC-209w31, SCHEMBL1539081, IYXVSRXFGYDNEV-UHFFFAOYSA-N, MolPort-001-785-471, ANW-45851, AR-1E5246, EBD103802, NSC-71547, WT1977, AKOS015998910, AJ-30322, AK-88636, CJ-06602, DA-00759, QC-10323, AB0004480, KB-236834, LS-123967, TC-134596, 4CH-011562, FT-0688423, ST24022978, W9617, 4-09-00-02329 (Beilstein Handbook Reference), 935-02-4 2-Propynenitrile, 3-phenyl- (9CI)

Removed Synonyms

CID96382, 99358-35-7

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