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419206

Sigma-Aldrich

Benzyl(triphenylphosphoranylidene)acetate

97%

Synonym(s):

(Benzyloxycarbonylmethylene)triphenylphosphorane, 2-(Triphenylphosphoranylidene)acetic acid phenylmethyl ester

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About This Item

Linear Formula:
(C6H5)3P=CHCO2CH2C6H5
CAS Number:
Molecular Weight:
410.44
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

assay

97%

reaction suitability

reaction type: C-C Bond Formation

mp

120-122 °C (lit.)

functional group

ester
phenyl
phosphine

SMILES string

O=C(OCc1ccccc1)C=P(c2ccccc2)(c3ccccc3)c4ccccc4

InChI

1S/C27H23O2P/c28-27(29-21-23-13-5-1-6-14-23)22-30(24-15-7-2-8-16-24,25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20,22H,21H2

InChI key

INKMLGJBBDRIQR-UHFFFAOYSA-N

Application

Reactant for:
  • Tributylphosphine-mediated vinylogous Wittig reactions
  • Synthesis of 1,2-dioxanes for antitrypanosomal activity
  • Organocatalytic Michael-type reactions / Wittig reactions of phosphorus ylides and unsaturated ketones
  • Stereoselective phosphine-catalyzed cycloaddition to form spirocyclopenteneoxindoles
  • Enantioselective synthesis of pantothenic acid
  • Preparation of phosphorus ylides from phosphoranes and acetic anhydride

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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