32271-55-9

Basic information

• Product Name: (3E)-4-(4-bromophenyl)-3-buten-2-ol
• Synonyms: (3E)-4-(4-bromophenyl)-3-buten-2-ol
• CAS NO: 32271-55-9
• Molecular Weight: 227.101
• Mol File: 32271-55-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (3E)-4-(4-bromophenyl)-3-buten-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3E)-4-(4-bromophenyl)-3-buten-2-ol(32271-55-9)
• EPA Substance Registry System: (3E)-4-(4-bromophenyl)-3-buten-2-ol(32271-55-9)

Safety Data

• Hazardous Substances Data: 32271-55-9(Hazardous Substances Data)

Upstream product

• 20511-04-0 (E)-4-(4-bromophenyl)but-3-ene-2-one 
• 64-17-5 ethanol 
• 1200-07-3 trans-4-bromocinnamic acid 
• 598-32-3 2-hydroxy-3-butene 
• 106-40-1 4-bromo-aniline 
• 49678-04-8 trans-4-bromocinnamaldehyde 
• 1122-91-4 4-bromo-benzaldehyde 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 917-54-4 methyllithium 
• 7647-01-0 hydrogenchloride 
• 54450-58-7 1-(4-Bromophenyl)-2(E)-buten-1-ol 

Downstream Products

• 1587713-34-5 (Z)-4-(4-(4-bromophenyl)but-3-en-2-yl)morpholine 
• 1587713-47-0 (R,E)-4-(4-(4-bromophenyl)but-3-en-2-yl)morpholine 
• 1587713-48-1 (R, Z)-4-(4-(4-bromophenyl)but-3-en-2-yl)morpholine 
• 1587713-14-1 (E)-1-(4-(4-bromophenyl)but-3-en-2-yl)pyrrolidine 
• 1587713-15-2 (E)-1-(4-(4-bromophenyl)but-3-en-2-yl)piperidine 
• 1587713-16-3 (E)-4-(4-(4-bromophenyl)but-3-en-2-yl)morpholine 
• 1587713-32-3 (Z)-1-(4-(4-bromophenyl)but-3-en-2-yl)pyrrolidine 
• 1587713-33-4 (Z)-1-(4-(4-bromophenyl)but-3-en-2-yl)piperidine 
• 1471095-04-1 C₁₂H₁₃BrO₂ 
• 1587713-49-2 (R,E)-4-(4-bromophenyl)but-3-en-2-yl acetate 
• 1373490-26-6 (E)-2-(4-(4-bromophenyl)but-3-en-2-yl)-1,3-diphenylpropane-1,3-dione 
• 1373490-28-8 (E)-2-(4-(4-bromophenyl)but-3-en-2-yl)-5-methylthiophene 
• 690257-96-6 (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol 
• 1251857-72-3 (E)-1-bromo-4-(3-tosylbut-1-enyl)benzene 

Relevant articles and documents

Sequential Two-Step Stereoselective Amination of Allylic Alcohols through the Combination of Laccases and Amine Transaminases

A sequential two-step chemoenzymatic methodology for the stereoselective synthesis of (3E)-4-(het)arylbut-3-en-2-amines in a highly selective manner and under mild reaction conditions is described. The approach consists of oxidation of the corresponding racemic alcohol precursors by the use of a catalytic system made up of the laccase from Trametes versicolor and the oxy-radical TEMPO, followed by the asymmetric reductive bio-transamination of the corresponding ketone intermediates. Optimisation of the oxidation reaction, exhaustive amine transaminase screening for the bio-transaminations and the compatibility of the two enzymatic reactions were studied in depth in search of a design of a compatible sequential cascade. This synthetic strategy was successful and the combinations of enzymes displayed a broad substrate scope, with 16 chiral amines being obtained in moderate to good isolated yields (29–75 %) and with excellent enantiomeric excess values (94 to >99 %). Interestingly, both amine enantiomers can be achieved, depending on the selectivity of the amine transaminase employed in the system.

Silver-catalyzed decarboxylative C(sp2)-C(sp3) coupling reactions: Via a radical mechanism

A silver catalyzed decarboxylative C(sp2)-C(sp3) coupling of vinylic carboxylic acids with alcohols, alkylbenzenes, cycloalkanes and cyclic ethers was developed by using DTBP as an oxidant. This reaction tolerates a wide range of substrates, and products are obtained in good to excellent yields. The reaction also shows good stereoselectivity, and only trans-isomers are obtained. In addition, a radical pathway would be involved to facilitate this decarboxylative C(sp2)-C(sp3) coupling reaction.

Facile synthesis of Z -alkenes via uphill catalysis

Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.