91150-58-2

Basic information

• Product Name: 3-(4'-bromo-2'-thiophenyl)-(E)-propenoic acid methyl ester
• CAS NO: 91150-58-2
• Molecular Weight: 247.112
• Mol File: 91150-58-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-(4'-bromo-2'-thiophenyl)-(E)-propenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4'-bromo-2'-thiophenyl)-(E)-propenoic acid methyl ester(91150-58-2)
• EPA Substance Registry System: 3-(4'-bromo-2'-thiophenyl)-(E)-propenoic acid methyl ester(91150-58-2)

Safety Data

• Hazardous Substances Data: 91150-58-2(Hazardous Substances Data)

Usage

Chemical structure

(E)-3-(4'-bromo-2'-thiophenyl)propenoic acid methyl ester

Properties

contains a bromine atom, a thiophene ring, and a carboxylic acid group

Uses

may be used in various industrial and research applications, such as in the synthesis of other organic compounds or as a building block for more complex chemical structures

Handling

important to handle with care, as it may present certain hazards if not used properly

Upstream product

• 18791-75-8 4-Bromothiophen-2-aldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 872-31-1 3-Bromothiophene 
• 292638-85-8 acrylic acid methyl ester 
• 96-32-2 bromoacetic acid methyl ester 
• 67-56-1 methanol 
• 103686-16-4 trans-3-(4-bromothiophen-2-yl)propenoic acid 

Relevant articles and documents

Syntheses of some sulfur-containing polyunsaturated fatty acids as potential lipoxygenase inhibitors

Starting from (all-Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA) and (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), several polyunsaturated fatty acids, containing a sulfur atom either in the chain or in a thiophene ring, have been synthesized as potential inhibitors of lipoxygenases. Copyright Taylor & Francis Group, LLC.

Part I: The development of the catalytic wittig reaction

We have developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide precatalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was necessary to employ cyclic phosphane oxide precatalysts of type 1. Initial substrate studies utilized sodium carbonate as a base, and further experimentation identified N,N-diisopropylethylamine (DIPEA) as a soluble alternative. The use of DIPEA improved the ease of use, broadened the substrate scope, and decreased the precatalyst loading. The optimized protocols were compatible with alkyl, aryl, and heterocyclic (furyl, indolyl, pyridyl, pyrrolyl, and thienyl) aldehydes to produce both di- and trisubstituted olefins in moderate-to-high yields (60-96 %) by using a precatalyst loading of 4-10 mol %. Kinetic E/Z selectivity was generally 66:34; complete E selectivity for disubstituted α,β-unsaturated products was achieved through a phosphane-mediated isomerization event. The CWR was applied to the synthesis of 54, a known precursor to the anti-Alzheimer drug donepezil hydrochloride, on a multigram scale (12.2 g, 74 % yield). In addition, to our knowledge, the described CWR is the only transition-/heavy-metal-free catalytic olefination process, excluding proton-catalyzed elimination reactions. A point of difference: By utilizing an organosilane to chemoselectively reduce a phosphane oxide precatalyst to a phosphane (see scheme), the first catalytic (in phosphane) Wittig reaction has been developed. The methodology has been applied to the synthesis of 22 disubstituted and 24 trisubstituted olefins, including a multigram synthesis of a precursor to the anti-Alzheimer drug donepezil hydrochloride.

Recycling the waste: The development of a catalytic wittig reaction

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