Catalog Number
ACM1067874-1
Product Name
Diethyl Allylphosphonate, ≥95%
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.
Covalently-Bonded Unit Count
1
Exact Mass
178.075881g/mol
Monoisotopic Mass
178.075881g/mol