ETHYL CIS-3-BROMOACRYLATE

Base Information

• Chemical Name: ETHYL CIS-3-BROMOACRYLATE
• CAS No.: 31930-34-4
• Molecular Formula: C5H7 Br O2
• Molecular Weight: 179.013
• Hs Code.: 29161900
• Mol file: 31930-34-4.mol

Synonyms:2-Propenoicacid, 3-bromo-, ethyl ester, (Z)-; Acrylic acid, 3-bromo-, ethyl ester, (Z)-(8CI); (2Z)-3-Bromo-2-propenoic acid ethyl ester; Ethyl (Z)-3-bromopropenoate;cis-Ethyl 3-bromo-2-propenoate

Chemical Property of ETHYL CIS-3-BROMOACRYLATE

Chemical Property:

• Vapor Pressure: 1.25mmHg at 25°C
• Refractive Index: n20/D 1.481
• Boiling Point: 173.7°Cat760mmHg
• Flash Point: 58.9°C
• PSA: 26.30000
• Density: 1.475g/cm³
• LogP: 1.45810
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl cis-3-bromoacrylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-52/53-22
• Safety Statements: 26-36-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Ethyl cis-3-Bromoacrylate acts as a reagent in the synthetic preparation of aristeromycin and also in the preparation of lipoxin derivatives as new anti-inflammatory compounds. Ethyl cis-3-bromoacrylate was used in the preparation of ethyl 2-amino-9-(2-deoxy-β-D-erythropentofuranosyl)-6,9-dihydro-6-oxo-1H-purine-1-acrylate. It was used in the synthesis of 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,4-dihydropyrimido[1,2-a]purine-6,10-dione. It was employed as building block for the stereoselective preparation of cis-2-enoates.

Technology Process of ETHYL CIS-3-BROMOACRYLATE

There total 7 articles about ETHYL CIS-3-BROMOACRYLATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

propynoic acid ethyl ester (623-47-2) → ethyl (Z)-3-bromopropenoate (31930-34-4)

Guidance literature:

With acetic acid; lithium bromide; In acetonitrile; at 80 ℃;

DOI:10.1016/j.tetasy.2010.03.026

Reference yield:

ethyl (Z)-3-iodopropenoate (31930-36-6) → ethyl (Z)-3-bromopropenoate (31930-34-4)

Guidance literature:

With copper(l) iodide; tetramethylammonium bromide; trans-N,N'-dimethylcyclohexane-1,2-diamine; In ethanol; at 110 ℃; for 72h; stereospecific reaction; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tet.2016.07.018

Reference yield:

2-Brom-1-(diphenylboryl)-1-ethencarbonsaeure-ethylester (86429-06-3,86429-07-4) → ethyl (Z)-3-bromopropenoate (31930-34-4) + ethyl (E)-3-bromoacrylate (31930-35-5)

Guidance literature:

With acetic acid; In pentane; Yield given. Yields of byproduct given. Title compound not separated from byproducts; 0 deg C to r.t.;

upstream raw materials:

2-Brom-1-(diphenylboryl)-1-ethencarbonsaeure-ethylester

propynoic acid ethyl ester

ethyl (Z)-3-iodopropenoate

3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester

Downstream raw materials:

ethyl 6-phenylhex-5-yn-(2Z)-enoate

cis-3-bromo-2-propen-1-ol

Diethyl trans-hex-3-enedioate

cis-3-Hexendicarbonsaeurediaethylester

Refernces

• 1、 Ivon, Yevhen M.,Kuchkovska, Yuliya O.,Voitenko, Zoya V.,Grygorenko, Oleksandr O.. "Aliphatic α-Boryl-α-bromoketones: Synthesis and Reactivity". . p. 3367 - 3377. Retrieved 2020/03/13.
• 2、 Nitelet, Antoine,Jouvin, Kévin,Evano, Gwilherm. "Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B". . p. 5972 - 5987. Retrieved 2016/09/16.