Synthesis of diphenylphosphoryl azide

Preparation of diphenylphosphoryl azide

Alternative Names: Diphenyl phosphoryl azide; Diphenyl azidophosphate; Diphenylphosphonic azide; DPPA;

Preparation of diphenylphosphoryl azide

Preparation of diphenylphosphoryl azide

A mixture of 56.8 g (0.24 mole) of diphenyl chlorophosphate and 46.3 g (0.25 mole) of sodium azide in dry acetone is stirred at room temperature for 24 hours. The filtered solution is concentrated on a rotary evaporator and the obtained residue is distilled under vacuum (0.15 mmHg) at 152-155 °C. The yield of diphenylphosphoryl azide is 53.3 g (92%) as a colorless oil.

Chem. Pharm. Bull., 22, 849-845 (1974)

IUPAC Name

[azido(phenoxy)phosphoryl]oxybenzene

InChI

InChI=1S/C12H10N3O3P/c13-14-15-19(16,17-11-7-3-1-4-8-11)18-12-9-5-2-6-10-12/h1-10H

InChI Key

SORGEQQSQGNZFI-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)OP(=O)(N=[N+]=[N-])OC2=CC=CC=C2

MeSH Synonyms

diphenyl phosphoryl azide, diphenylphosphorazidate, diphenylphosphoryl azide

Depositor-Supplied Synonyms

Diphenylphosphoryl azide, Diphenyl phosphoryl azide, Diphenyl azidophosphate, 26386-88-9, Diphenylphosphonic azide, DPPA, DPPA polymer-bound, diphenyl phosphorazidate, PS-DPPA, {[azido(phenoxy)phosphoryl]oxy}benzene, Diphenylphosphorazidate, phosphorazidic acid diphenyl ester, Diphenyl azidophosphonate, Phosphorazidic acid, diphenyl ester, Diphenyl phosphonyl azide, Phosphoric acid diphenyl ester azide, Diphenylphosphoryl azide, polymer-bound, SORGEQQSQGNZFI-UHFFFAOYSA-N, SBB057862, AZIDOPHOSPHORIC ACID DIPHENYL ESTER, (azido(phenoxy)phosphoryl)oxybenzene, [azido(phenoxy)phosphoryl]oxybenzene, (diazoazamvinyl)diphenoxyphosphino-1-one, ([AZIDO(PHENOXY)PHOSPHORYL]OXY)BENZENE, Diphenylazidophosphate, Diphenylphosphonoazide, diphenoxyphosphinylazide, diphenylphosphoroazidate, AC1NWBTX, PubChem12386, diphenoxyphosphoryl azide, diphenyl phosphoroazidate, diphenylphosphoric azide;, AC1Q1UHI, AC1Q1UHJ, AC1L3WJ7, DIPHENYL PHOSPHORAZIDE, UNII-GXM91165AV, SCHEMBL80417, 178756_ALDRICH, 668168_ALDRICH, GXM91165AV, Jsp005184, CTK7I1877, Phosphorazidic acid,diphenyl ester, diazonio(diphenoxyphosphoryl)azanide, ACT03265, EBD42812, EINECS 247-644-0, ZINC04352551, AKOS009159231, AB00183, AM86815, LS40117, MCULE-6114124392, RP28573, O891, OR007435, AB0005966, DB-007439, FT-0080164, ST51007165, AZ0001-0393, EN300-55951, A-7816, 3B3-004309

Removed Synonyms

diphenylphosphorylazide, Diphenyl phosphorylazide, (azido-phenoxy-phosphoryl)oxybenzene, CID123414, CID5702712, D1672

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