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280933

Sigma-Aldrich

(Triphenylphosphoranylidene)acetaldehyde

95%

Synonym(s):

(Formylmethylene)triphenylphosphorane

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About This Item

Linear Formula:
HCOCH=P(C6H5)3
CAS Number:
2136-75-6
Molecular Weight:
304.32
Beilstein/REAXYS Number:
523797
EC Number:
218-375-6
MDL number:
MFCD00006994
UNSPSC Code:
12352114
PubChem Substance ID:
24856960
NACRES:
NA.22

assay

95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

185-188 °C (lit.)

SMILES string

[H]C(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C20H17OP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H

InChI key

CQCAYWAIRTVXIY-UHFFFAOYSA-N

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Application

Wittig reagent for the conversion of aldehydes and ketones to two-carbon homologated, α,β-unsaturated carbonyl compounds.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jian Wang et al.
Organic letters, 9(18), 3703-3706 (2007-08-19)
The first total synthesis of (-)-aplysiallene has been completed in 16 steps and features a key sequential Mukaiyama aerobic oxidative cyclization to prepare the fused bis-THF core. The original stereochemical assignment has been revised as shown.
Tohru Nagamitsu et al.
The Journal of organic chemistry, 72(8), 2744-2756 (2007-03-16)
The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to

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