31058-93-2

Basic information

• Product Name: 2-bromo-3-methylbut-2-enal
• Synonyms: 2-Bromo-3-methyl-2-butenal; 2-butenal, 2-bromo-3-methyl-; Crotonaldehyde, 2-bromo-3-methyl-
• CAS NO: 31058-93-2
• Molecular Formula: C₅H₇BrO
• Molecular Weight: 163.0125
• Mol File: 31058-93-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 197.1°C at 760 mmHg
• Flash Point: 86.2°C
• Density: 1.42g/cm³
• Vapor Pressure: 0.384mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: 2-bromo-3-methylbut-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-3-methylbut-2-enal(31058-93-2)
• EPA Substance Registry System: 2-bromo-3-methylbut-2-enal(31058-93-2)

Safety Data

• Hazardous Substances Data: 31058-93-2(Hazardous Substances Data)

Upstream product

• 58898-20-7 1,1-dibromo-2,2-dimethyl-3-trimethylsilanyloxy-cyclopropane 
• 85371-47-7 β,β-dibromovinyl methyl ether 
• 67-64-1 acetone 
• 99414-72-9 2,3-dibromo-3-methylbutanal 
• 107-86-8 3,3-dimethyl acrylaldehyde 

Downstream Products

• 89005-38-9 3-methyl-2-phenylsulfanylbut-2-enal 

Relevant articles and documents

Synthesis of the Taxol Core via Catalytic Asymmetric 1,4-Addition of an Alkylzirconium Nucleophile

The Taxol core was prepared in five steps via a key copper-catalyzed asymmetric conjugate addition trapping sequence. The use of a bromodiene-derived alkylzirconium nucleophile followed by trapping with POCl3/DMF gave a highly functionalized intermediate featuring a quaternary center in 69% yield with 92% ee. After 1,2-addition, Suzuki-Miyaura cross-coupling, allylic oxidation, and a type II intramolecular Diels-Alder reaction, the taxol core was obtained in 11% overall yield with 92% ee.

Sequential O-Arylation/Lanthanide(III)-Catalyzed [3,3]-Sigmatropic Rearrangement of Bromo-Substituted Allylic Alcohols

Lanthanide(III)-catalyzed aryl-Claisen rearrangement of substrates bearing halo-substituted allyl groups, specifically 2-bromoallyl aryl ethers, afford ortho -2-bromoallylphenols. Aryl ether substrates were synthesized from brominated allylic alcohols via Mitsunobu reaction, Cu(II)-catalyzed arylation using potassium aryltrifluoroborate salts, or S N Ar reaction. Aryl-Claisen rearrangements proceeded in moderate to excellent yields using Eu(III) catalysis. The alkenylbromide functionality remains intact, illustrating the compatibility of synthetically important alkenylhalides during C-O/C-C σ-bond migration processes. Subsequent derivatization of the ortho -2-bromoallylphenol products through O-alkylation or C-arylation/alkenylation via Suzuki-Miyaura cross-coupling demonstrate the potential to access densely-functionalized molecules.

Enantioselective Preparation of Polyfunctional Secondary Allylic Alcohols Using Functionalized Dialkylzincs Prepared by a Copper(I) Catalyzed Iodine-Zinc Exchange Reaction.

Catalytic amounts of Cu(I) salts considerably facilitate the iodine-zinc exchange reaction leading to polyfunctional dialkylzincs.The catalytic asymmetric addition of these zinc reagents to a wide range of α,β-unsaturated aldehydes provides polyfunctional allylic alcohols with a high enantioselectivity.