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2091-46-5 - Propargyltriphenylphosphonium bromide, 97% - Triphenylpropargylphosphonium bromide - Triphenyl-2-propyn-1-ylphosphonium bromide - A12753 - Alfa Aesar

A12753 Propargyltriphenylphosphonium bromide, 97%

CAS Number
2091-46-5
Synonyms
Triphenylpropargylphosphonium bromide
Triphenyl-2-propyn-1-ylphosphonium bromide

Size Price ($) Quantity Availability
5g 36.67
25g 128.75
100g 387.28
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Propargyltriphenylphosphonium bromide, 97%

MDL
MFCD00011811
EINECS
218-242-2

Chemical Properties

Formula
C21H18BrP
Formula Weight
381.26
Melting point
177-182°
Sensitivity
Hygroscopic
Solubility
Soluble in methanol.

Applications

Propargyltriphenylphosphonium bromide can be used in the alcylation of amines. It is a commonly used as a Wittig reagent.

Notes

Hygroscopic. Store in cool dry place in tightly closed container. With good ventilation. Store away from oxidizing agent and water/moisture.

Literature References

M.H. Wahdan; A.A. Hermas; M.S. Morad. Corrosion inhibition of carbon-steels by propargyltriphenylphosphonium bromide in H2SO4 solution. Materials Chemistry and Physics. 2002, 76(2), 111-118.

Yeong-Soon Gal. A Facile Synthetic Method of Poly(Propargyltriphenylphosphonium-Tetraphenylborate) Via Ion Exchange Reaction of Poly(Propargyltriphenylphosphonium Bromide) Using Tetraphenylboron Sodium. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry. 1995, 321031-1038.

Precursor of enynes by the Wittig reaction: Liebigs Ann. Chem., 682, 62 (1965); J. Org. Chem., 42, 200 (1977); see Appendix 1.

Readily undergoes additions with nucleophiles, e.g. alcohols or amines, to give 2-alkoxy or 2-alkylamino propenyl phosphonium salts. In these reactions, the reactive species is the allenic isomer, propadienyl triphenylphosphonium bromide: J. Org. Chem., 42, 200 (1977). By using a chiral alcohol, the subsequent base-promoted Wittig reaction with carbonyl compounds yields amino or alkoxy dienes which undergo face-selective Diels-Alder additions to dienophiles: J. Chem. Soc., Chem. Commun., 1785 (1995):

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P280h-P305+P351+P338

Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Other References

Beilstein
3579775
Harmonized Tariff Code
2931.90
TSCA
No

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