Phenyl phosphorodichloridate

• Catalog No.: A10479
• CAS Number: 770-12-7
• M. F.: C6H5Cl2O2P
• M. W.: 210.982461
• Purity: 97%

SYNONYMS

• Title: 二氯磷酸苯酯
• IUPAC name: phenoxyphosphonoyl dichloride
• IUPAC Traditional name: phenyl dichlorophosphate
• Synonyms: Phenyl dichlorophosphate

DATABASE IDS

• EC Number: 212-220-6
• CAS Number: 770-12-7
• Beilstein Number: 511863
• MDL Number: MFCD00002067

PROPERTIES

• Purity: 97%
• Boiling Point: 241-243°C
• Density: 1.415
• Flash Point: 112°C(233°F)
• Melting Point: -1°C
• Refractive Index: 1.5230
• GHS Hazard statements: H301-H310-H314-H318
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Risk Statements: 22-27-34
• RTECS: TD4393000
• Safety Statements: 26-28-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2922
• Packing Group: II

REFERENCES

• Reagent for the preparation of phosphate diesters. The phenyl group is removable by hydrogenolysis: J. Am. Chem. Soc., 75, 4510 (1953).
• Coupling reagent, e.g. in pyridine for the preparation of derivatives of sulfinic acids with alcohols, amines, thiols etc.: Synthesis, 937 (1980). Similarly, carboxylic acids in pyridine can be coupled with thiols to give thiocarboxylic acid S-esters: Can. J. Chem., 58, 2645 (1980), and with sodium azide in the presence of a phase-transfer catalyst to give acyl azides: Synth. Commun., 13, 289 (1983).
• Reacts with the Li enolates of ?-diketones, in the presence of LiCl, to give ?-chloro-ɑ?-enones: Can. J. Chem., 64, 520 (1986).
• In combination with NaI, cleaves dialkyl ethers to iodides in high yield: Synth. Commun., 18, 119 (1988), and 1,3-dithianes and other dithioacetals to carbonyl groups: Tetrahedron Lett., 29, 5471 (1988).
• In combination with Dimethyl sulfoxide, A13280, effects selective oxidation of alcohols to aldehydes or ketones with less ɑ-chlorination than the more usual Swern (Oxalyl chloride, A18012) system: J. Org. Chem., 52, 5621 (1987). Similarly, benzylamines have been converted to benzaldehydes: Synth. Commun., 19, 3407 (1989).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1651 (2004).