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Sigma-Aldrich

(Methoxymethyl)triphenylphosphonium chloride

97%

Synonym(s):

Triphenyl(methoxymethyl)phosphonium chloride

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About This Item

Linear Formula:
(C6H5)3P(Cl)CH2OCH3
CAS Number:
4009-98-7
Molecular Weight:
342.80
Beilstein:
3599844
EC Number:
223-664-5
MDL number:
MFCD00011800
UNSPSC Code:
12352107
PubChem Substance ID:
24858739
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

185-195 °C (dec.) (lit.)

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

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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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H315,H319,H411

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

>482.0 °F

Flash Point(C)

> 250 °C

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 the akuammiline alkaloid picrinine
Smith JM, et al.
Journal of the American Chemical Society, 136(12), 4504-4507 (2014)
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)
Stereoselective total synthesis of (+)-artemisinin
Yadav JS, et al.
Tetrahedron Letters, 44(2), 387-389 (2003)
A convenient synthesis of quinolines by reactions of o-isocyano-β-methoxystyrenes with nucleophiles
Kobayashi K, et al.
Tetrahedron, 60(50), 11639-11645 (2004)

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