Synthesis of trimethyl phosphate

Preparation of trimethyl phosphate (trimethylphosphate; phosphoric acid, trimethyl ester; trimethyl orthophosphate; TMPA)

Preparation of trimethyl phosphate (trimethylphosphate; phosphoric acid, trimethyl ester; trimethyl orthophosphate; TMPA)

Preparation of trimethyl phosphate (trimethylphosphate; phosphoric acid, trimethyl ester; trimethyl orthophosphate; TMPA)

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. 61 ml (48 g) of dry methyl 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 trimethyl phosphate is purified by distillation in a vacuum. The fraction boiling at 62°/5 mm is collected yielding pure trimethyl phosphate.

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

IUPAC Name

trimethyl phosphate

InChI

InChI=1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3

InChI Key

WVLBCYQITXONBZ-UHFFFAOYSA-N

Canonical SMILES

COP(=O)(OC)OC

MeSH Synonyms

trimethyl phosphate, trimethylphosphate

Depositor-Supplied Synonyms

TRIMETHYL PHOSPHATE, Trimethylphosphate, 512-56-1, Phosphoric acid, trimethyl ester, Trimethyl orthophosphate, TMPA, TMPO, Phosphoric acid trimethyl ester, Trimethoxyphosphine oxide, O,O,O-Trimethyl phosphate, Trimethylfosfat, NCI-C03781, Phosphate, trimethyl-, Trimethylfosfat [Czech], NSC 58985, CCRIS 610, Methyl phosphate, (MeO)3PO, CHEBI:46324, HSDB 5090, WVLBCYQITXONBZ-UHFFFAOYSA-N, EINECS 208-144-8, SBB060441, AI3-05905, DSSTox_CID_1403, DSSTox_RID_76141, DSSTox_GSID_21403, TZZ, CAS-512-56-1, dimethylphosphonomethanol, trimethyl phosphoric acid, ACMC-1AMD5, bmse000774, UNII-Z1E45TMW1Z, AC1L1VF1, AC1Q6SF8, Z1E45TMW1Z, SCHEMBL19941, (CH3O)3PO, KSC489Q4N, WLN: 1OPO&O1&O1, 132195_ALDRICH, 241024_ALDRICH, CHEMBL1236486, CTK3I9846, MolPort-001-768-918, NSC58985, Tox21_201576, Tox21_302740, ANW-31220, NSC-58985, ZINC01689472, AKOS009029142, LS-1318, RP20577, RTR-018269, TRA0079572, NCGC00248617-01, NCGC00248617-02, NCGC00256562-01, NCGC00259125-01, phosphoric acid trimethyl ester
TMP, AN-23494, CJ-06429, CJ-28004, TR-018269, FT-0689821, FT-0695119, P0271, ST51046615, 85093-EP2305657A2, 85093-EP2305808A1, 85133-EP2292624A1, 85133-EP2305808A1, A804739, 3B4-0446, I14-16586, InChI=1/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H, methyl phosphate,
trimethoxyphosphine oxide
trimethyl orthophosphate, 91316-44-8

Removed Synonyms

METHYL PHOSPHATE, CID10541, TMP, C003715, 121-45-9

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