Synthesis of valeronitrile

Preparation of valeronitrile

Preparation of valeronitrile

Preparation of valeronitrile

30 g of dry sodium cyanide (dried at 110º C overnight a) are mixed with 150 ml of dry dimethyl sulfoxide. The mixture is added to the flask fitted with a stirrer, reflux condenser, dropping funnel, and thermometer. The thick reaction slurry is heated to 90º C and the heating then  is stopped.  0.5 mole of 1-chlorobutane  is slowly added to the stirred mixture causing the temperature to increase immediately. The rate of addition is such that the temperature of the reaction did not go above about 160º C. After all the 1-chlorobutane is added the mixture is stirred for additional 10 min. more, or until the temperature dropped below 50º C. After the reaction is complete the mixture is poured into water and the product extracted several times with chloroform or ethyl ether. The extract is washed several times with saturated sodium chloride solution, dried over calcium chloride, and the valeronitrile is distilled at 139º C yielding 93% of the final product.

J. Org. Chem., 1960, 25 (2), pp 257–258





InChI Key


Canonical SMILES


MeSH Synonyms


Depositor-Supplied Synonyms

VALERONITRILE, Pentanenitrile, 110-59-8, Butyl cyanide, n-Valeronitrile, n-BUTYL CYANIDE, 1-Cyanobutane, 1-Butyl cyanide, CCRIS 6114, RFFFKMOABOFIDF-UHFFFAOYSA-N, EINECS 203-781-8, BRN 1736706, AI3-30052, Pentanonitrile, n-Butylcyanide, n-Pentanenitrile, Butane, 1-cyano-, ACMC-1BPOU, DSSTox_CID_6275, AC1L1Q6C, DSSTox_RID_78085, DSSTox_GSID_26275, KSC178S6F, CH3(CH2)3CN, UNII-X44H3R47D4, 155098_ALDRICH, 45927_RIEDEL, Jsp000808, CHEMBL1503158, 94590_FLUKA, CTK0H8962, MolPort-001-783-811, LTBB002006, X44H3R47D4, ZINC2041071, Tox21_200282, 7395AF, ANW-16170, LS-509, ZINC02041071, AKOS000200376, MCULE-4015236167, RL00440, RTR-002171, TRA0016344, NCGC00091673-01, NCGC00091673-02, NCGC00257836-01, AN-43011, CAS-110-59-8, CJ-07648, CJ-32481, LP067277, OR019828, SC-25761, DB-040932, TR-002171, FT-0631617, 104618-EP2380568A1, 4-02-00-00875 (Beilstein Handbook Reference), A802223, I14-5877, T7101764, InChI=1/C5H9N/c1-2-3-4-5-6/h2-4H2,1H, 3B3-017178

Removed Synonyms

C5H9N, CID8061, V0008

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