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

A10479 Phenyl phosphorodichloridate, 97%

Número CAS
770-12-7
Nombre Alternativo
Phenyl dichlorophosphate

Tamaño Precio ($) Cantidad Disponibilidad
25g 23,60
100g 57,90
500g 244,00
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Phenyl phosphorodichloridate, 97%

MDL
MFCD00002067
EINECS
212-220-6

Propiedades químicas

Fórmula
C6H5Cl2O2P
Peso molecular
210.98
Punto de fusión
-1°
Punto de ebullición
241-243°
Punto de inflamabilidad
112°(233°F)
Densidad
1.415
Índice de refracción
1.5230
Sensibilidad
Moisture Sensitive
Solubilidad
Immiscible with water.

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H302-H314-H318

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

Indicaciones de precaución: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
511863
Clase de peligro
8
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2919.90
TSCA
Yes
RTECS
TD4393000

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