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

L09919 Diethyl chlorophosphite, 97%

CAS Number
589-57-1
Synonyms
Diethyl phosphorochloridite

Size Price ($) Quantity Availability
5g 34.29
25g 101.70
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Diethyl chlorophosphite, 97%

MDL
MFCD00009074
EINECS
209-652-2

Chemical Properties

Formula
C4H10ClO2P
Formula Weight
156.55
Boiling Point
153-155°
Flash Point
25°(77°F)
Density
1.082
Refractive Index
1.4375
Sensitivity
Air & Moisture Sensitive
Solubility
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.

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H226

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

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

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

Other References

Merck
14,3841
Beilstein
1098392
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2920.90
TSCA
Yes

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