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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
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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signalword
Warning
hcodes
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
| SKU | GTIN |
|---|---|
| 309567-25G | 04061826676097 |
| 309567-100G | 04061826676059 |

