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309567

(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:
Molecular Weight:
342.80
UNSPSC Code:
12352107
NACRES:
NA.22
PubChem Substance ID:
EC Number:
223-664-5
Beilstein/REAXYS Number:
3599844
MDL number:
Assay:
97%
Form:
solid
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Quality Level

assay

97%

form

solid

reaction suitability

core: phosphonium, 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

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.



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pictograms

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Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

>482.0 °F

flash_point_c

> 250 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves



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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)
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)



Global Trade Item Number

SKUGTIN
309567-25G04061826676097
309567-100G04061826676059