159377-42-1

Basic information

• Product Name: (Isopropyloxycarbonylmethyl)triphenylphonium bromide
• Synonyms: (Isopropyloxycarbonylmethyl)triphenylphonium bromide
• CAS NO: 159377-42-1
• Molecular Formula: C23H24BrO2P
• Molecular Weight: 443.313221
• Mol File: 159377-42-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 150-151 °C
• Appearance: /
• CAS DataBase Reference: (Isopropyloxycarbonylmethyl)triphenylphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: (Isopropyloxycarbonylmethyl)triphenylphonium bromide(159377-42-1)
• EPA Substance Registry System: (Isopropyloxycarbonylmethyl)triphenylphonium bromide(159377-42-1)

Safety Data

• Hazardous Substances Data: 159377-42-1(Hazardous Substances Data)

Usage

General Description

(Isopropyloxycarbonylmethyl)triphenylphosphonium bromide is a chemical compound with the formula C27H27BrO2P. It is a quaternary ammonium salt that is commonly used as a phase transfer catalyst in organic synthesis. (Isopropyloxycarbonylmethyl)triphenylphonium bromide has a wide range of applications, particularly in the pharmaceutical and chemical industries. It serves as a versatile reagent for the preparation of various organic compounds, including pharmaceutical intermediates and agrochemicals. The presence of the isopropyloxycarbonylmethyl group and the triphenylphosphonium bromide moiety gives this compound its unique properties, allowing it to facilitate the transfer of a wide range of organic and inorganic species between immiscible phases. Overall, (Isopropyloxycarbonylmethyl)triphenylphosphonium bromide is a valuable chemical reagent with diverse applications in organic synthesis.

Upstream product

• 29921-57-1 isopropyl 2-bromoacetate 
• 603-35-0 triphenylphosphine 

Relevant articles and documents

Phosphine-catalyzed synthesis of 6-substituted 2-pyrones: Manifestation of E/Z-isomerism in the zwitterionic intermediate

(Chemical Equation Presented) We report a one-step phosphine-catalyzed annulation between aldehydes and ethyl allenoate to form 6-substituted 2-pyrones. The mechanistic rationale for this reaction requires explicit discussion of the E/Z-isomerism of the zwitterionic intermediate formed by the addition of a phosphine to the allenoate. Sterically demanding trialkylphosphines facilitate the shift of equilibrium toward the E-isomeric zwitterion and lead to the formation of 6-substituted 2-pyrones. Various aromatic as well as aliphatic aldehydes undergo the transformation in moderate to excellent yield.

NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates

An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.

Thermal decomposition of triphenylphosphonium alkyl ester salts

In thermolyses of molten triphenylphosphonium alkyl ester bromides and chlorides, alkyl = methyl, ethyl, isopropyl, at 130 and 225°C, initial attack of the halide ion on the methyl group gives the methyl halide and ylid 1, Ph3P = CH2, which can be methylated, or is protonated by the phosphonium salt with transylidation giving Ph3P+-CH3X-, X = Br, Cl. The initial reactions of the ethyl or isopropyl esters are with the halide ion, X-, as a base giving ylid, 1, which can be protonated by HX or by transylidation. The t-butyl ester generates Ph3P+-CH3X-but no products of transylidation. The first-formed ylid1, can be trapped by reactive alkyl and acyl halides, and the transient ylidic esters decompose thermally to triphenyl phosphine oxide, Ph3P = O, react further with unreacted phosphonium ester, or are trapped by added aldehyde in a Wittig reaction. The final product compositions are affected by a decrease in pressure, due to escape of volatile intermediates, and by replacement of the X- halide ion by the less nucleophilic and basic tosylate ion. Reactions under reflux, in solution in chloroform, or in suspension in benzene, are similar to those of the molten salts, but yields are generally lower at the lower temperatures. Copyright Taylor & Francis Group, LLC.