MilliporeSigma
All Photos(1)

Documents

C5106

Sigma-Aldrich

(Carbethoxymethylene)triphenylphosphorane

95%

Sign Into View Organizational & Contract Pricing

Synonym(s):
(Ethoxycarbonylmethylene)triphenylphosphorane, Ethyl (triphenylphosphoranylidene)acetate
Linear Formula:
(C6H5)3P=CHCO2CH2CH3
CAS Number:
Molecular Weight:
348.37
Beilstein/REAXYS Number:
754639
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
157929280933158755
reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

crystals

form

powder

form

solid

form

solid

mp

128-130 °C (lit.)

mp

168-172 °C (lit.)

mp

185-188 °C (lit.)

mp

203-205 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service