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C5106

Sigma-Aldrich

(Carbethoxymethylene)triphenylphosphorane

95%

Synonym(s):

(Ethoxycarbonylmethylene)triphenylphosphorane, Ethyl (triphenylphosphoranylidene)acetate

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About This Item

Linear Formula:
(C6H5)3P=CHCO2CH2CH3
CAS Number:
1099-45-2
Molecular Weight:
348.37
Beilstein:
754639
EC Number:
214-151-7
MDL number:
MFCD00009183
UNSPSC Code:
12352108
PubChem Substance ID:
24892754
NACRES:
NA.22

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

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.

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
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)

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