Skip to Content
Merck
All Photos(1)

Key Documents

309567

Sigma-Aldrich

(Methoxymethyl)triphenylphosphonium chloride

97%

Synonym(s):

Triphenyl(methoxymethyl)phosphonium chloride

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
(C6H5)3P(Cl)CH2OCH3
CAS Number:
Molecular Weight:
342.80
Beilstein:
3599844
EC Number:
MDL number:
UNSPSC Code:
12352107
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

185-195 °C (dec.) (lit.)

functional group

ether
phosphine

SMILES string

[Cl-].COC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C20H20OP.ClH/c1-21-17-22(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20;/h2-16H,17H2,1H3;1H/q+1;/p-1

InChI key

SJFNDMHZXCUXSA-UHFFFAOYSA-M

Looking for similar products? Visit Product Comparison Guide

Application

(Methoxymethyl)triphenylphosphonium chloride is a Wittig reagent that reacts with aldehydes and ketones to give substituted alkenes. This Wittig reaction finds application as the key step in the synthesis of:
  • Antimalarial drug, (+)-artemisinin.
  • Substituted quinolines.
  • Akuammiline alkaloid picrinine.
  • 7H-pyrrolo[2,3-d]pyrimidine derivatives for signal transducers and activators of transcription 6 (STAT6) inhibitors.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

>482.0 °F

Flash Point(C)

> 250 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Total synthesis of the akuammiline alkaloid picrinine
Smith JM, et al.
Journal of the American Chemical Society, 136(12), 4504-4507 (2014)
Stereoselective total synthesis of (+)-artemisinin
Yadav JS, et al.
Tetrahedron Letters, 44(2), 387-389 (2003)
Novel 7H-pyrrolo [2, 3-d] pyrimidine derivatives as potent and orally active STAT6 inhibitors
Nagashima S, et al.
Bioorganic & Medicinal Chemistry, 17(19), 6926-6936 (2009)
A convenient synthesis of quinolines by reactions of o-isocyano-β-methoxystyrenes with nucleophiles
Kobayashi K, et al.
Tetrahedron, 60(50), 11639-11645 (2004)

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