Synthesis of triisopropyl phosphate

Preparation of triisopropyl phosphate (triisopropylphosphate; phosphoric acid, tris(1-methylethyl) ester; tripropan-2-yl phosphate)

Preparation of triisopropyl phosphate (triisopropylphosphate; phosphoric acid, tris(1-methylethyl) ester; tripropan-2-yl phosphate)

Preparation of triisopropyl phosphate (triisopropylphosphate; phosphoric acid, tris(1-methylethyl) ester; tripropan-2-yl phosphate)

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. 115 ml (90 g) of dry isopropyl 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 triisopropyl phosphate is purified by distillation in a vacuum. The fraction boiling at 83.5°/5 mm is collected yielding pure triisopropyl phosphate.

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

Org. Synth. 1936, 16, 9

IUPAC Name

tripropan-2-yl phosphate

InChI

InChI=1S/C9H21O4P/c1-7(2)11-14(10,12-8(3)4)13-9(5)6/h7-9H,1-6H3

InChI Key

OXFUXNFMHFCELM-UHFFFAOYSA-N

Canonical SMILES

CC(C)OP(=O)(OC(C)C)OC(C)C

MeSH Synonyms

triisopropyl phosphate

Depositor-Supplied Synonyms

Triisopropyl phosphate, Triisopropylphosphate, 513-02-0, Phosphoric acid, tris(1-methylethyl) ester, tripropan-2-yl phosphate, OXFUXNFMHFCELM-UHFFFAOYSA-N, Isopropyl phosphate, (C3H7O)3PO, ACMC-20ajdw, tri(isopropyl) phosphate, AC1Q6SC2, NCIOpen2_002645, SCHEMBL80155, tris(propan-2-yl) phosphate, 554669_ALDRICH, Phosphoric acid, triisopropyl ester, AC1L2987, NSC46370, NSC62275, EINECS 208-150-0, AR-1J2786, NSC 46370, NSC-46370, NSC-62275, AKOS025295406, CJ-27460, TC-164795, Phosphoric acid, tris(1-methylethyl) ester (9CI), 3B3-052797

Removed Synonyms

ISOPROPYL PHOSPHATE, CID68188, C011560, 5259-31-4

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