Synthesis of tripentyl phosphate

Preparation of tripentyl phosphate

Alternative Names: tri-n-amylphosphate; phosphoric acid triamyl ester; phosphoric acid, tripentyl ester

Preparation of tripentyl phosphate (tri-n-amylphosphate; phosphoric acid triamyl ester; phosphoric acid, tripentyl ester)

Preparation of tripentyl phosphate (tri-n-amylphosphate; phosphoric acid triamyl ester; phosphoric acid, tripentyl ester)

A 1-liter four-necked flask is fitted with an efficient condenser, an air-tight stirrer, a short-stemmed dropping funnel and a thermometer. Calcium chloride tubes are attached to the top of dropping funnel and the reflux condenser. 163.1 ml (132 g) of dry n-pentyl alcohol, 132.5 ml (130 g) of dry pyridine and 140 ml of dry benzene are placed in the flask, which is stirred and cooled in an ice-salt mixture until the temperature falls to – 5° C. 40.5 ml (76.5 g) of freshly redistilled (b.p. 106-107° C) phosphorus oxychloride are dropwise added from the funnel at such a rate that the temperature does not rise above 10° C. When all phosphorus oxychloride has been added the reaction mixture is gently refluxed for 2 hours and cooled to room temperature. 250 ml of water are added in order to dissolve the pyridine hydrochloride, the benzene layer is separated, washed several times with water until the washings are neutral, and dried over anhydrous sodium or magnesium sulfate. The benzene is removed by evaporation and crude tripentyl phosphate is purified by distillation in a vacuum. The fraction boiling at 167.5°/5 mm is collected yielding pure tripentyl phosphate.

A text book of practical organic chemistry, by A. I. Vogel, 304, 1974

Org. Synth. 1936, 16, 9

IUPAC Name

tripentyl phosphate

InChI

InChI=1S/C15H33O4P/c1-4-7-10-13-17-20(16,18-14-11-8-5-2)19-15-12-9-6-3/h4-15H2,1-3H3

InChI Key

QJAVUVZBMMXBRO-UHFFFAOYSA-N

Canonical SMILES

CCCCCOP(=O)(OCCCCC)OCCCCC

Depositor-Supplied Synonyms

Tripentyl phosphate, tri-n-Amylphosphate, Phosphoric Acid Triamyl Ester, 2528-38-3, Triamyl Phosphate, Phosphoric acid, tripentyl ester, EINECS 219-773-2, NSC 202805, Tripentyl phosphate #, ACMC-209giu, AC1Q6SZU, AC1L2P9A, SCHEMBL56777, CTK3J2615, QJAVUVZBMMXBRO-UHFFFAOYSA-, QJAVUVZBMMXBRO-UHFFFAOYSA-N, ANW-25684, AR-1L7551, NSC202805, AKOS015856750, NSC-202805, RTR-031411, Phosphoric acid, tripentyl ester (8CI), LS-107882, TR-031411, P0265, Phosphoric acid, tripentyl ester (8CI)(9CI), 3B3-052747, I14-103015, InChI=1/C15H33O4P/c1-4-7-10-13-17-20(16,18-14-11-8-5-2)19-15-12-9-6-3/h4-15H2,1-3H3

Removed Synonyms

CID75665, 25764-15-2

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