(Carbomethoxymethyl)triphenylphosphonium bromide Chemical Properties

Melting point:

165-170 °C (dec.) (lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in methanol(almost transparency).

form 

solid

color 

White to Almost white

Sensitive 

Hygroscopic

BRN 

3812975

InChIKey

VCWBQLMDSMSVRL-UHFFFAOYSA-M

CAS DataBase Reference

1779-58-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

9

HS Code 

29319019

MSDS

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• Language:English Provider:SigmaAldrich
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(Carbomethoxymethyl)triphenylphosphonium bromide Usage And Synthesis

Chemical Properties

white powder

Uses

(Methoxycarbonylmethyl)triphenylphosphonium bromide is a reactant for the synthesis of GSK-3 inhibitors using the Wittig reaction, substituted furanones for antifungal and cytostatic activities, photochromic dithienylethene derivatives, gem-diiodoalkanes containing allylic alcohols and highly substituted cyclopentenes and brazilanes via Au-catalyzed deoxygenative Nazarov cyclization. As reactant for asymmetric hydrogenation of α,β-unsaturated ester-phosphonates, studies of thermal decomposition of phosphonium alkyl ester salts.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

To a stirred ethyl acetate solution of triphenylphosphine (1.7 g, 6.7 mmol), an ethyl acetate solution of methyl 2-bromoacetate (0.62 μL, 6.5 mmol) was slowly added at room temperature. The reaction mixture was stirred at room temperature for 17 h to produce a white precipitate. The precipitate was collected by filtration and washed three times with ether, followed by drying in air to afford (2-methoxy-2-oxoethyl)triphenylphosphonium bromide (4, 2.49 g) as a white solid in near quantitative yield. The resulting phosphonium bromide 4 (2.0 g, 4.81 mmol) was added to an ethanol (10 mL) suspension of sodium ethanolate (340 mg), followed by the slow addition of 3a (1.15 g, 4.75 mmol) over a period of 25 min at room temperature. The reaction mixture was stirred at 50-55 °C for 1 h, during which the progress of the reaction was monitored by TLC. Upon completion of the reaction, water (10 mL) was added to the reaction mixture and the product was extracted four times with ether (20 mL). The organic layers were combined, dried with anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent to give a solid residue. Further purification by column chromatography (eluent: ethyl acetate/hexane, 3:7) afforded a 3.5:1 mixture of E- and Z-cinnamic acid methyl ester derivatives.

Purification Methods

Wash it with pet ether (b 40-50o), recrystallise it from CHCl3/Et2O and dry it at high vacuum at 65o. [Isler et al. Helv Chim Acta 40 1242 1957, Wittig & Haag Chem Ber 88 1654, 1664 1955, Beilstein 16 IV 981.]

References

[1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2017, vol. 72, # 2, p. 119 - 124
[2] European Journal of Organic Chemistry, 2002, # 13, p. 2094 - 2108
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 5, p. 1188 - 1208
[4] Helvetica Chimica Acta, 2003, vol. 86, # 2, p. 310 - 323
[5] Heterocycles, 2007, vol. 73, # C, p. 751 - 768

(Carbomethoxymethyl)triphenylphosphonium bromide(1779-58-4)Related Product Information

• Tetraphenylphosphonium bromide
• Dichloromethylphenylsilane
• DICHLOROTRIPHENYLPHOSPHORANE
• Anisole
• Methyltriphenylphosphonium iodide
• Triphenylphosphine oxide
• Triphenylphosphine
• TETRAPHENYLPHOSPHINE IMIDE
• Ethyltriphenylphosphonium bromide
• METHOXYTRIMETHYLSILANE
• Tetrakis(triphenylphosphine)palladium
• Allyl bromide
• Triphenylphosphine hydrobromide
• (Trifluoromethoxy)benzene
• Sodium bromate
• Phenylmagnesium bromide
• Tris(triphenylphosphine)chlororhodium
• Rocuronium bromide