phenoxyphosphonoyl dichloride

• ChemBase ID: 75024
• Molecular Formular: C6H5Cl2O2P
• Molecular Mass: 210.982461
• Monoisotopic Mass: 209.94042139
• SMILES: O(c1ccccc1)P(=O)(Cl)Cl
• Canonical SMILES: ClP(=O)(Oc1ccccc1)Cl
• InChI: InChI=1S/C6H5Cl2O2P/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H
• InChIKey: TXFOLHZMICYNRM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenoxyphosphonoyl dichloride
• IUPAC Traditional name: phenyl dichlorophosphate
• Synonyms: Phenyldichlorophosphate; Phenyl phosphorodichloridate 97%; Phenyl dichlorophosphate; Phenyl dichlorophosphate; Phenyl phosphorodichloridate; Phenyl phosphorodichloridate; Phenyl phosphoryl dichloride; Phenyl phosphodichloridate; PHENYL DICHLOROPHOSPHATE; 二氯化磷酸苯酯; 苯基磷二氯化物; 苯氧基磷酰二氯; 二氯磷酸苯酯

Database IDs

• CAS Number: 770-12-7
• EC Number: 212-220-6
• MDL Number: MFCD00002067
• Beilstein Number: 511863
• PubChem SID: 162039942; 24898297
• PubChem CID: 13038

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.546608
• LogD (pH = 7.4): 2.546608
• Log P: 2.546608
• Molar Refractivity: 46.0552 cm^3
• Polarizability: 18.186308 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -1°C
• Boiling Point: 196°C; 241-243 °C(lit.); 241-243°C
• Flash Point: 112°C(233°F); 113 °C; 235.4 °F
• Density: 1.412 g/mL at 25 °C(lit.); 1.415; 1.42 g/ml
• Refractive Index: 1.5230; n20/D 1.523(lit.)

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Moisture Sensitive
• RTECS: TD4393000
• European Hazard Symbols: Corrosive (C); Highly toxic (T+)
• UN Number: 3265; UN2922
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 22-27-34; 34-37
• Safety Statements: 26-28-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H310-H314-H318; H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-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: ≥95%; 97%
• Linear Formula: C6H5OP(O)Cl2

DETAILS

MP Biomedicals - 02151826

1 ml = approx. 1.42 g
Acetylcholinesterase inhibitor

Sigma Aldrich - P22389

Packaging
25, 100 g in glass bottle
Application
Reagent for the preparation of phosphate diesters.1

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).