Diethyl Allylphosphonate, ≥95%

Name: Diethyl Allylphosphonate, ≥95%
SKU: ACM1067874-1
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Catalog NumberACM1067874-1

CAS Number1067-87-4

CategoryMonomers

IUPAC Name

3-diethoxyphosphorylprop-1-ene

Molecular Weight

178.17g/mol

Molecular Formula

C7H15O3P

Canonical SMILES

CCOP(=O)(CC=C)OCC

InChI

InChI=1S/C7H15O3P/c1-4-7-11(8,9-5-2)10-6-3/h4H,1,5-7H2,2-3H3

InChI Key

YPJHXRAHMUKXAE-UHFFFAOYSA-N

Application

Diethyl Allylphosphonate, ≥95%, is a versatile clear colorless liquid used as a reactant in various advanced chemical syntheses. Its purpose lies in enabling significant reactions such as the copolymerization of phosphonated allyl monomers with maleic anhydride and facilitating enantioselective synthesis of complex structures like solamin-type mono-THF acetogenins. It plays a crucial role in ring-closing metathesis reactions leading to oxaphospholene and oxaphosphinene heterocycles and aids in the synthesis of spongistatin 2 via Wittig coupling. Moreover, it supports the stereoselective synthesis of intricate furanosteroids and the preparation of protected polyhydroxylated β-amino acids, vital constituents of microsclerodermins. Diethyl Allylphosphonate is pivotal in C-C bond formation reactions, highlighted by its refined addition process involving controlled interaction with aldehydes to yield (E)-1-aryl/alkylbutadienes, and is instrumental within metathesis reactions with dimethyl vinylphosphonate under specific conditions.

Complexity

146

Covalently-Bonded Unit Count

EC Number

619-646-5

Exact Mass

178.075881g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

178.075881g/mol

Rotatable Bond Count