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1779-49-3 - Methyltriphenylphosphonium bromide, 98+% - A15878 - Alfa Aesar

A15878 Methyltriphenylphosphonium bromide, 98+%

CAS Number
1779-49-3
Synonyms

Size Price ($) Quantity Availability
50g 28.43
250g 95.18
1000g 331.48
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Methyltriphenylphosphonium bromide, 98+%

MDL
MFCD00011804
EINECS
217-218-9

Chemical Properties

Formula
CH3P(C6H5)3Br
Formula Weight
357.24
Melting point
231-234°
Sensitivity
Hygroscopic
Solubility
Soluble in water.

Applications

Methyltriphenylphosphonium bromide is used for methylenation through the Wittig reaction. It is utilized in the synthesis of an enyne and 9-isopropenyl -phenanthrene by using sodium amide as reagent. It is a lipophilic molecule and used to deliver molecules to specific cell components. Further, it acts as an antineoplastic agent.

Notes

Hygroscopic. Incompatible with strong oxidizing agents.

Literature References

Precursor of Wittig ylide for methylenation of carbonyl compounds (see Appendix 1). See, e.g.: Org. Synth. Coll., 5, 751 (1973). A simplified procedure using K2CO3 in triglyme has been reported: Synth. Commun., 22, 513 (1992).

Where the ylide is insufficiently reactive, a further proton can be removed by s-BuLi or t-BuLi, and the resulting lithio ylide reacted with hindered ketones such as fenchone: J. Am. Chem. Soc., 104, 4724 (1982). Reaction of the lithio ylide with an epoxide generates a new ylide, with which Wittig olefination of aldehydes gives trans-homoallylic alcohols (same ref.):

Aissaoui, T.; AlNashef, I. M.; Hayyan, M.; Hashim, M. A. Neoteric FT-IR investigation on the functional groups of phosphonium-based deep eutectic solvents. Spectrochim. Acta Mol. Biomol. Spectrosc. 2015, 149, 588-591.

Chou, Y. H.; Takasugi, S.; Goseki, R.; Ishizone, T.; Chen, W. C. Nonvolatile organic field-effect transistor memory devices using polymer electrets with different thiophene chain lengths. Polym. Chem. 2014, 5 (3), 1063-1071.

GHS Hazard and Precautionary Statements

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

Harmful if swallowed. 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
3599467
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
Yes

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