diphenyl chlorophosphonate

• ChemBase ID: 137349
• Molecular Formular: C12H10ClO3P
• Molecular Mass: 268.632761
• Monoisotopic Mass: 268.00560849
• SMILES: c1ccc(cc1)OP(=O)(Oc1ccccc1)Cl
• Canonical SMILES: ClP(=O)(Oc1ccccc1)Oc1ccccc1
• InChI: InChI=1S/C12H10ClO3P/c13-17(14,15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
• InChIKey: BHIIGRBMZRSDRI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenyl chlorophosphonate
• IUPAC Traditional name: diphenyl chlorophosphonate
• Synonyms: Diphenyl chlorophosphate; Diphenyl phosphorochloridate; Diphenyl phosphoryl chloride; Diphenyl chlorophosphate; Diphenyl phosphoryl chloride; Diphenyl phosphorochloridate; 二苯基氯磷酸酯; 二苯磷酰氯; 氯磷酸二苯酯

Database IDs

• CAS Number: 2524-64-3
• EC Number: 219-759-6
• MDL Number: MFCD00003030
• Beilstein Number: 654130
• PubChem SID: 24861235; 24893614; 162231612
• PubChem CID: 75654

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.8171308
• LogD (pH = 7.4): 3.8171308
• Log P: 3.8171308
• Molar Refractivity: 66.7434 cm^3
• Polarizability: 26.448591 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 145-147°C/1mm; 314-316 °C/272 mmHg(lit.)
• Flash Point: >113 °C; >235.4 °F; 113°C(235°F)
• Density: 1.296; 1.296 g/mL at 25 °C(lit.)
• Refractive Index: 1.5500; n20/D 1.55(lit.)
• Vapor Pressure: 10 mmHg ( 190 °C)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34; 34-37
• Safety Statements: 20-26-36/37/39-45-60; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

Product Information

• Purity: 96%; 97%; 99%
• Linear Formula: (C6H5O)2POCl

DETAILS

Sigma Aldrich - 344249

Packaging
100, 500 g in glass bottle

Sigma Aldrich - D206555

Packaging
25, 100 g in glass bottle
Application
Phosphorylation reagent for protected serine1 and pyranoses.2

REFERENCES

• Diphenylphosphate esters, formed with or without catalysis by DMAP, undergo a variety of transformations:
• Hydrogenolysis of the phenyl groups yields the monophosphate ester of the alcohol. Glycosyl monophosphates have been prepared in this way. Alternatively, treatment of the glycosyl diphenyl phosphate with sodium azide in DMF provides a high yield route to glycosyl azides: Carbohydr. Res., 223, 169 (1992).
• Diphenylphosphate has also been exploited as a good leaving group in the high yield conversion (equivalent to dehydration) of secondary alcohols to olefins by thermal elimination: Synthesis, 1300 (1995). For further information, see Triphenyl phosphate, L08130. Other conversions, generally in the presence of a base such as triethylamine, in which the equivalent of a dehydration step occurs are:
• Aldoximes to nitriles at room temperature: J. Org. Chem., 34, 2805 (1969). Peptide coupling (see Appendix 6), via the mixed carboxyl phosphate anhydride: Chem. Ber., 94, 2644 (1961). Carboxylic acids to anhydrides: Synthesis, 219 (1981). ω-Hydroxy acids to macrolides, promoted by DMAP: J. Org. Chem., 47, 1612 (1982).
• Lithium enolates give enol diphenylphosphates in which the phosphate moiety acts as a leaving group; e.g., ketone enol phosphates have been converted to the corresponding alkene by reaction with organocuprates: Tetrahedron Lett., 4405 (1976). With amides, internal displacement occurs; subsequent reaction with NaN₃ gives azirines: Helv. Chim. Acta, 76, 2830 (1993):
  
• See also Diphenylphosphonic azide, A12124.