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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
Pricing and availability is not currently available.

Quality Level

200

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.[1][2] It is used as a reagent in the total synthesis of compounds such as (−)-oseltamivir,[3] (+)-nakadomarin A[4] and (−)-dictyostatin.[5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
HMBK5030
HMBK4180
HMBK1628
HMBK3535
HMBK2531

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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)
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)
The first total synthesis of nakadomarin A
Nagata T, et al.
Journal of the American Chemical Society, 125(25), 7484-7485 (2003)
Total synthesis of (−)-dictyostatin
O'Nei GW and Phillips AJ
Journal of the American Chemical Society, 128(16), 5340-5341 (2006)

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