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

A10479 Phenyl phosphorodichloridate, 97%

Codice CAS
770-12-7
Sinonimi
Phenyl dichlorophosphate

Dimensioni Prezzo ($) Quantità Disponibilità
25g 21,06
100g 56,16
500g 224,10
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Phenyl phosphorodichloridate, 97%

MDL
MFCD00002067
EINECS
212-220-6

Proprietà chimiche

Formula
C6H5Cl2O2P
Peso formula
210.98
Punto di fusione
-1°
Punto di ebollizione
241-243°
Punto di infiammabilità
112°(233°F)
Densità
1.415
Indice di rifrazione
1.5230
Sensibilità
Moisture Sensitive
Solubilità
Immiscible with water.

Applicazioni

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.

Note

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

Letteratura

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): H314-H318-H302

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

Dichiarazioni precauzionali: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P301+P312-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Immediately call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
511863
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2919.90
TSCA
Yes
RTECS
TD4393000

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