All Photos(1)
Synonym(s):
(Ethoxycarbonylmethylene)triphenylphosphorane, Ethyl (triphenylphosphoranylidene)acetate
Linear Formula:
(C6H5)3P=CHCO2CH2CH3
CAS Number:
Molecular Weight:
348.37
Beilstein:
754639
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
Assay
95%
form
crystals
reaction suitability
reaction type: C-C Bond Formation
mp
128-130 °C (lit.)
storage temp.
2-8°C
SMILES string
CCOC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3
InChI
1S/C22H21O2P/c1-2-24-22(23)18-25(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h3-18H,2H2,1H3
InChI key
IIHPVYJPDKJYOU-UHFFFAOYSA-N
Related Categories
Application
(Carbethoxymethylene)triphenylphosphorane is a Horner-Wittig reagent generally used in Horner−Wadsworth−Emmons (HWE) reaction. It is used as a reagent in the total synthesis of compounds such as (−)-oseltamivir, (+)-nakadomarin A and (−)-dictyostatin.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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High-yielding synthesis of the anti-influenza neuraminidase inhibitor (−)-oseltamivir by two ?one-pot? sequences
Ishikawa H, et al.
Chemistry?A European Journal , 16(42), 12616-12626 (2010)
Total synthesis of (−)-dictyostatin
O'Nei GW and Phillips AJ
Journal of the American Chemical Society, 128(16), 5340-5341 (2006)
The first total synthesis of nakadomarin A
Nagata T, et al.
Journal of the American Chemical Society, 125(25), 7484-7485 (2003)
Scope and limitation of the reactions of 3-imino derivatives of pentane-2, 4-diones with organophosphorus reagents
Boulos LS, et al.
Phosphorus, Sulfur, and Silicon and the Related Elements, 187(6), 697-710 (2012)
Nucleophilicity parameters for phosphoryl-stabilized carbanions and phosphorus ylides: Implications for wittig and related olefination reactions
Appel R, et al.
Journal of the American Chemical Society, 131(2), 704-714 (2008)
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