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1530-32-1 - Ethyltriphenylphosphonium bromide, 98+% - B23096 - Alfa Aesar

B23096 Ethyltriphenylphosphonium bromide, 98+%

CAS Number
1530-32-1
Synonyms

Size Price ($) Quantity Availability
25g 25.47
100g 72.04
500g 258.14
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Ethyltriphenylphosphonium bromide, 98+%

MDL
MFCD00011838
EINECS
216-223-3

Chemical Properties

Formula
C20H20BrP
Formula Weight
371.26
Melting point
206-210°
Flash Point
>200°(392°F)
Sensitivity
Hygroscopic
Solubility
Soluble in methanol. Slightly soluble in water, acetone and isopropanol.

Applications

Ethyltriphenylphosphonium bromide acts as a reactant in the synthesis of D-amino acids from L-cysteine-derived thiazolidines, Leiodolide A through aldol reactions and Horner-Wadsworth-Emmons olefination. It is also used in the preparation of cycloalkanoindolines through diastereoselective intramolecular inimo-ene reactions. Further, it is used as a reagent in solid-state metathesis polycondensation to prepare alkyl-dipropenylthiophene monomers and Mizoroki-Heck cyclization and cascading Tsuji-Trost cyclization reactions.

Notes

Hygroscopic. Incompatible with oxidizing agents.

Literature References

Reaction of the phosphorane (generated using 1 mole of n-BuLi) with an aldehyde at low temperature, followed by a second mole of n-BuLi, gives the -oxido phosphonium ylide which can then be reacted with 1,2-diiodoethane to give (Z)-2-iodo-2-alkenes with high stereoselectivity: J. Chem. Soc., Perkin 1, 1331 (1995). See Appendix 1.

Bagh, F. S. G.; Shahbaz, K.; Mjalli, F. S.; Hashim, M. A.; AlNashef, I. M. Zinc(II) chloride-based deep eutectic solvents for application as electrolytes: Preparation and characterization. J. Mol. Liq. 2015, 204, 76-83.

Harada, K.; Imai, A.; Uto, K.; Carter, R. G.; Kubo, M.; Hioki, H.; Fukuyama, Y. Synthesis of jiadifenin using Mizoroki-Heck and Tsuji-Trost reactions. Tetrahedron 2015, 71 (15), 2199-2209.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H312-H315-H319-H335-H411-H401

Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Toxic to aquatic life with long lasting effects. Toxic to aquatic life.

Precautionary Statements: P261-P273-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. 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. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
3599630
Hazard Class
9
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
Yes

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