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770-12-7 - Phenyl phosphorodichloridate, 97% - Phenyl dichlorophosphate - A10479 - Alfa Aesar

A10479 Phenyl phosphorodichloridate, 97%

Codice CAS
Phenyl dichlorophosphate

Dimensioni Prezzo ($) Quantità Disponibilità
25g 23,60
100g 57,90
500g 244,00
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Phenyl phosphorodichloridate, 97%


Proprietà chimiche

Peso formula
Punto di fusione
Punto di ebollizione
Punto di infiammabilità
Indice di rifrazione
Moisture Sensitive
Immiscible with water.


Reagent for preparation of phosphate diesters.Phenyl phosphorodichloridate is used in the preparation of symmetrical phosphate diesters. It is used as a phosphorylating agent for alcohols and amines. It is also involved in the preparation of phenylphosphoro di-(1-imidazolidate) and 2-phenyl-bis-triazoloylphosphate, which is used in peptide synthesis. It plays a vital role in the Pfitzner-Moffatt oxidation which involves oxidation of alcohols to the corresponding aldehydes and ketones. Furthermore, it is utilized in Beckmann rearrangement for the preparation of N-phenylacetamide from acetophenone oxime.


Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong bases, alcohols and strong oxidizing agents.


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 ß-diketones, in the presence of LiCl, to give ß-chloro-ɑß-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).

Kuo, C. W.; Hsieh, M. T.; Gao, S.; Shao, Y. M.; Yao, C. F.; Shia, K. S. Beckmann Rearrangement of Ketoximes Induced by Phenyl Dichlorophosphate at Ambient Temperature. Molecules 2012, 17 (11), 13662-13672.

Nagarkar, A. A.; Crochet, A.; Fromm, K. M.; Kilbinger, A. F. Efficient amine end-functionalization of living ring-opening metathesis polymers. Macromolecules 2012, 45 (11), 4447-4453.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H314-H318

Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P260u-P201-P280a-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310a-P405-P501a

Obtain special instructions before use. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

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