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589-57-1 - Diethyl chlorophosphite, 97% - Diethyl phosphorochloridite - L09919 - Alfa Aesar

L09919 Diethyl chlorophosphite, 97%

Numéro de CAS
589-57-1
Synonymes
Diethyl phosphorochloridite

Conditionnement Prix ($) Quantité Disponibilité
5g 36,70
25g 111,00
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Diethyl chlorophosphite, 97%

MDL
MFCD00009074
EINECS
209-652-2

Propriétés chimiques

Formule
C4H10ClO2P
Poids moleculaire
156.55
Point d'ébullition
153-155°
Point d'éclair
25°(77°F)
Densité
1.082
Indice de réfraction
1.4375
Sensibilité
Air & Moisture Sensitive
Solubilité
Soluble in DMSO and chloroform. Reacts with water.

Applications

Diethyl chlorophosphite acts as a versatile phosphorylating agent for ester and lactone enolates, amines and alkenols. It is used in the synthesis of organophosphates and are considered anticholinesterase agents through observation in studies.

Notes

Air & Moisture Sensitive. Store away from air and strong bases. Incompatible with water, bases, active metals and oxidizing agents.

Références bibliographiques

Bilha Fischer and Larisa Sheihet. Diethyl Chlorophosphite:? A Mild Reagent for Efficient Reduction of Nitro Compounds to Amines.J. Org. Chem.1998, 63 (2), 393-395.

George W. Anderson; Alice D. Welcher; Richard W. Young. Diethyl Chlorophosphite as a Reagent for Peptide Syntheses.J. Am. Chem. Soc.1951, 73 (1), 501-502.

Reacts readily with nucleophiles, e.g. amines, alcohols or organometallic species, with the introduction of a phosphorus substituent. The phosphorylation of OH groups has been brought about by treatment with the reagent followed by oxidation of the P(III) product to P(V) with, e.g. iodine: Synth. Commun., 12, 821 (1982); Synthesis, 572 (1986). The chlorophosphite has the advantage of greater reactivity over one-step phosphorylation reagents, e.g. Diphenyl­ phosphorochloridate, A13546.

Reagent for peptide coupling: J. Am. Chem. Soc., 74, 5304, 5309 (1952); see Appendix 6. Also useful, in the presence of TMS-OTf, in glycosidic couplings: Tetrahedron Lett., 33, 6123 (1992).

In the presence of N-ethyldiisopropylamine, reduces both aryl and alkyl nitro compounds to amines: J. Org. Chem., 63, 393 (1998). The reagent also effects dehydration of aldoximes to nitriles, deoxygenation of N-oxides and sulfoxides, and conversion of epoxides to chlorohydrins can also be effected: J. Org. Chem., 67, 711 (2002).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H314-H318

Flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,3841
Beilstein
1098392
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2920.29
TSCA
Yes

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Catalyseurs

Analytique et matériel de laboratoire