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5044-52-0 - Vinyltriphenylphosphonium bromide, 97% - Schweizer's Reagent - Triphenylvinylphosphonium bromide - L00708 - Alfa Aesar

L00708 Vinyltriphenylphosphonium bromide, 97%

CAS Number
5044-52-0
Synonyms
Schweizer's Reagent
Triphenylvinylphosphonium bromide

Size Price ($) Quantity Availability
5g 39.04
25g 77.76
100g 278.40
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Vinyltriphenylphosphonium bromide, 97%

MDL
MFCD00011807
EINECS
225-740-3

Chemical Properties

Formula
CH2=CHP(C5H5)3Br
Formula Weight
369.25
Melting point
182-186°
Sensitivity
Light Sensitive & Hygroscopic

Literature References

Conjugate additions of nucleophiles to the double bond give ß-substituted ethyl triphenylphosphonium salts which can be further reacted by Wittig olefination. Sequential reaction with phthalimide and an aldehyde leads, after hydrazinolysis of the resulting N-allylphthalimide, to 3-substituted allylamines: J. Org. Chem., 46, 3119 (1981). N-Alkyl allylamines can also be prepared from alkylamines: Tetrahedron Lett., 24, 3043 (1983):

/n

A variety of heterocyclic systems can be synthesized by conjugate addition and subsequent Wittig condensation: J. Am. Chem. Soc., 86, 2744, 2963 (1964); J. Org. Chem., 33, 2416 (1968). Use of carbon nucleophiles permits synthesis of carbocyclic systems: J. Org. Chem., 30, 2082 (1965).

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Conjugate addition of organocuprates leads to a new phosphonium salt which can be used in the Wittig olefination. With alkenyl cuprates this provides a stereoselective route to (Z,Z)-1,4-pentadienes: Tetrahedron Lett., 26, 1799 (1985). Sequential reactions, catalyzed by CuBr - Ag2CO3 or CuBr - H2O, with Grignard reagents and Wittig olefination with an aldehyde, have also been reported: J. Org. Chem., 61, 9659 (1996):

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GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
4168860
Harmonized Tariff Code
2931.90
TSCA
No

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