37428-55-0

Basic information

• Product Name: 2-Propen-1-ol, 3-bromo-, (2E)-
• Synonyms: (E)-3-bromo-2-propen-1-ol;(E)-3-bromo-prop-2-en-1-ol;3-bromo-2E-propenol;(E)-3-bromoprop-2-en-1-ol;E-3-bromoprop-2-en-1-ol;3t-bromo-allyl alcohol
• CAS NO: 37428-55-0
• Molecular Formula: C3H5BrO
• Molecular Weight: 136.976
• Mol File: 37428-55-0.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 2-Propen-1-ol, 3-bromo-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-ol, 3-bromo-, (2E)-(37428-55-0)
• EPA Substance Registry System: 2-Propen-1-ol, 3-bromo-, (2E)-(37428-55-0)

Safety Data

• Hazardous Substances Data: 37428-55-0(Hazardous Substances Data)

Upstream product

• 627-15-6 1,3-dibromopropene 
• 2060-25-5 3-bromoprop-2-yn-1-ol 
• 6213-89-4 (E)-3-bromoacrylic acid 
• 107-19-7 propargyl alcohol 
• 31930-34-4 ethyl (Z)-3-bromopropenoate 

Downstream Products

• 103197-98-4 (E)-hept-2-en-4-yn-1-ol 
• 32121-06-5 1,3-Dibromo-1-propene 
• 37675-31-3 1c-bromo-3-chloro-propene 
• 37675-31-3 (E)-1-bromo-3-chloroprop-1-ene 
• 1610714-35-6 (5-(hydroxymethyl)-isoxazol-3-yl)(phenyl)methanone 
• 139297-55-5 methyl 5-(hydroxymethyl)isoxazole-3-carboxylate 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 83413-35-8 (2E,5E)-6-phenylhexa-2,5-dien-1-ol 
• 71653-11-7 trans-β-bromoacrolein 
• 42238-15-3 (2E)-4-phenylbut-2-en-1-ol 
• 610272-48-5 1-[((E)-3-bromoallyloxy)methyl]benzene 
• 90108-30-8 methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate 
• 107644-50-8 (2E,8Z)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,8-dien-4-yn-1-ol 

Relevant articles and documents

Borylation and rearrangement of alkynyloxiranes: A stereospecific route to substituted α-enynes

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.

Rhodium-Catalyzed Oxidative C-H Allylation of Benzamides with 1,3-Dienes by Allyl-to-Allyl 1,4-Rh(III) Migration

The Rh(III)-catalyzed oxidative C-H allylation of N-acetylbenzamides with 1,3-dienes is described. The presence of allylic hydrogens cis to the less substituted alkene of the 1,3-diene is important for the success of these reactions. With the assistance of reactions using deuterated 1,3-dienes, a proposed mechanism is provided. The key step is postulated to be the first reported examples of allyl-to-allyl 1,4-Rh(III) migration.

3-Chloro-1-lithiopropene, a functional organolithium reagent, and its reactions with alkylboronates to give 3-alkylprop-1-en-3-ols

The reagent 3-chloro-1-lithiopropene (4) can be generated by treating 1-bromo-3-chloropropene with t-BuLi. It is unstable but if generated at low temperature in the presence of alkylboronic esters, such as 3, is trapped in situ to give rearrangement products 2, which on oxidation give 3-alkylprop-1-en-3-ols in good yields. The reaction works for primary, secondary, benzylic, and even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group available using organoborane chemistry and incorporating all features of such groups.