31930-34-4

Basic information

• Product Name: ETHYL CIS-3-BROMOACRYLATE
• Synonyms: ETHYL (Z)-3-BROMO-2-PROPENOATE;ETHYL CIS-3-BROMOACRYLATE;CIS-3-BROMOACRYLIC ACID ETHYL ESTER;(2Z)-3-Bromoacrylic acid ethyl ester;(2Z)-3-Bromopropenoic acid ethyl ester;(Z)-3-Bromoacrylic acid ethyl ester;(Z)-3-Bromopropenoic acid ethyl ester;Ethyl (Z)-3-bromo-2-propenoate,99%
• CAS NO: 31930-34-4
• Molecular Formula: C₅H₇BrO₂
• Molecular Weight: 179.01
• Product Categories: C2 to C5;Carbonyl Compounds;Esters
• Mol File: 31930-34-4.mol

Chemical Properties

• Boiling Point: 75 °C (12 mmHg)
• Flash Point: 58.9°C
• Appearance: /
• Density: 1.48 g/mL at 20 °C
• Vapor Pressure: 1.25mmHg at 25°C
• Refractive Index: n20/D 1.481
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• BRN: 1902817
• CAS DataBase Reference: ETHYL CIS-3-BROMOACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL CIS-3-BROMOACRYLATE(31930-34-4)
• EPA Substance Registry System: ETHYL CIS-3-BROMOACRYLATE(31930-34-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-52/53-22
• Safety Statements: 26-36-61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• F: 19
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 31930-34-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
ETHYL CIS-3-BROMOACRYLATE is used as a reagent for the synthetic preparation of aristeromycin, an antibiotic with potential applications in treating bacterial infections. It is also used in the preparation of lipoxin derivatives, which are new anti-inflammatory compounds that may help in managing inflammation-related conditions.
Used in Organic Chemistry:
ETHYL CIS-3-BROMOACRYLATE is employed as a building block for the stereoselective preparation of cis-2-enoates, which are important intermediates in the synthesis of various organic compounds. Additionally, it was used in the preparation of ethyl 2-amino-9-(2-deoxy-β-D-erythropentofuranosyl)-6,9-dihydro-6-oxo-1H-purine-1-acrylate and 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,4-dihydropyrimido[1,2-a]purine-6,10-dione, showcasing its utility in the synthesis of complex organic molecules.

InChI:InChI=1/C5H7BrO2/c1-2-8-5(7)3-4-6/h3-4H,2H2,1H3/b4-3-

Upstream product

• 1263187-14-9 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester 
• 31930-36-6 ethyl (Z)-3-iodopropenoate 
• 623-47-2 propynoic acid ethyl ester 
• 86429-06-3 2-Brom-1-(diphenylboryl)-1-ethencarbonsaeure-ethylester 

Downstream Products

• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 559062-83-8 ethyl (2Z)-4-phenyl-2-butenoate 
• 2833-20-7 ethyl (4E)-undeca-2,4-dienoate 
• 38447-06-2 ethyl (2Z,4E)-5-phenyl-2,4-pentadienoate 
• 1330776-49-2 C₃₁H₃₉F₃N₂O 
• 1330776-50-5 C₃₁H₃₉F₃N₂O 
• 1330776-51-6 C₃₁H₃₉F₃N₂O 
• 1330776-52-7 C₂₉H₄₀N₂ 
• 1330776-53-8 C₂₉H₄₀N₂ 
• 1330776-54-9 C₂₉H₄₀N₂ 

Relevant articles and documents

Diastereo- and Enantioselective Cross-Couplings of Secondary Alkylcopper Reagents with 3-Halogeno-Unsaturated Carbonyl Derivatives

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Aliphatic α-Boryl-α-bromoketones: Synthesis and Reactivity

A protocol for the preparation of α-boryl-α-bromoketones from alkenyl MIDA boronates was developed and applied to functionalized aliphatic derivatives. The reaction sequence included regioselective hydroxybromination of olefin moiety, followed by oxidation of alcohol group with Dess–Martin periodinane. The target trifunctional boronate-containing derivatives were obtained in up to 94 % yield over two steps starting from alkenyl MIDA boronates. In some cases, functional groups present in the substrate participated in the bromohydroxylation step via intramolecular nucleophilic attack at the bromonium cation leading to cyclic products. Additionally, the reactivity of aliphatic α-boryl-α-bromoketones was illustrated by nucleophilic substitution at the α-C atom and heterocyclization reactions.

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.

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Give me a ring? An efficient approach has been developed for the intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides catalyzed by palladium (see scheme). From a synthetic viewpoint, this method is highly attractive because the catalyst loading is low, the optimized reaction conditions are mild, and the substrate scope is broad. Copyright

Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes

Isomerically pure trans-and cis-γ-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti-and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (≤50% ee) has been attained.

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