4957-34-0

Basic information

• Product Name: Acetic acid 3-broMo-1-propenyl ester
• Synonyms: Acetic acid 3-broMo-1-propenyl ester;3-Bromo-1-propen-1-ol acetate;1-Acetoxy-3-bromo-1-propene
• CAS NO: 4957-34-0
• Molecular Formula: C₅H₇BrO₂
• Molecular Weight: 179.01188
• EINECS: -0
• Mol File: 4957-34-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acetic acid 3-broMo-1-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid 3-broMo-1-propenyl ester(4957-34-0)
• EPA Substance Registry System: Acetic acid 3-broMo-1-propenyl ester(4957-34-0)

Safety Data

• Hazardous Substances Data: 4957-34-0(Hazardous Substances Data)

Upstream product

• 506-96-7 Acetyl bromide 
• 107-02-8 acrolein 

Downstream Products

• 409093-35-2 5-[5-(tert-butyldimethylsiloxy)-2-(4-methylbenzenesulfonylamino)phenyl]-5-hydroxypent-2-enoic acid methyl ester 
• 1354789-85-7 (2R,3S)-ethyl 3-acetoxy-2-hydroxy-2-((S)-hydroxy(phenyl)methyl)pent-4-enoate 
• 1354789-86-8 (4S,5S)-ethyl 4-((S)-1-acetoxyallyl)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carboxylate 
• 1080025-42-8 C₂₀H₂₅NO₆ 
• 1080025-40-6 C₂₀H₂₅NO₇ 

Relevant articles and documents

Large-scale synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

The higher-carbon sugar L-glycero-D-manno-heptose is a major constituent of the inner core region of the lipopolysaccharide (LPS) of many Gram-negative bacteria. All preparative routes used to date require multiple steps, and scalability has been rarely addressed. Here a highly practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose by a simple four-step sequence starting from L-lyxose is disclosed. Only two recrystallisations are required and the process was demonstrated on a >100 mmol scale, yielding 41 g of the target compound. A practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose in four simple steps from L-lyxose is disclosed. The process requires only two recrystallisations and was demonstrated on a >100 mmol scale, allowing rapid access to this important bacterial sugar building block in a convenient storage form.

3-Bromopropenyl esters in organic synthesis: Indium- and zinc-mediated entries to alk-1-ene-3,4-diols

Metallic indium and zinc readily add to 3-bromopropenyl acetate (5) and benzoate (6) either in THF or in water, affording the corresponding 3-acyloxyallyl organometallic compounds. Nucleophilic addition to aldehydes opens a route to alk-l-ene-3,4-diols 2 in good to excellent yields. Two synthetic protocols were developed, the former involving indium in THF under Grignard conditions and the latter involving zinc in aqueous ammonium chloride under Barbier conditions. The diastereo-selectivity, under all the conditions examined, mainly depends on the nature of the carbonyl compound; conjugated aldehydes afford syn adducts 2, while unconjugated aldehydes display the opposite anti stereopreference.

The first zinc-promoted, environmentally friendly, and highly efficient acetoxyallylation of aldehydes in aqueous ammonium chloride

An exceptionally mild acetoxyallylation of aldehydes in water promoted by zinc is reported, using 3-bromo-1-acetoxyprop-1-ene as starting material; simple diastereoselectivity mainly depends on the nature of the aldehyde.