Ethyl 2-(bromomethyl)acrylate

Base Information

• Chemical Name: Ethyl 2-(bromomethyl)acrylate
• CAS No.: 17435-72-2
• Molecular Formula: C6H9BrO2
• Molecular Weight: 193.04
• Hs Code.: 29161900
• Mol file: 17435-72-2.mol

Synonyms:Acrylicacid, 2-(bromomethyl)-, ethyl ester (7CI,8CI);2-(Bromomethyl)-2-propenoic acidethyl ester;2-Carbethoxyallyl bromide;Ethyl 2-(bromomethyl)-2-propenoate;Ethyl 2-(bromomethyl)propenoate;Ethyl3-bromo-2-(methylene)propanoate;Ethyl 3-bromo-2-methylenepropionate;Ethylbromomethacrylate;Ethyl a-(bromomethyl)acrylate;Ethyl a-bromomethacrylate;NSC 215252;2-Propenoic acid,2-(bromomethyl)-, ethyl ester;

Chemical Property of Ethyl 2-(bromomethyl)acrylate

Chemical Property:

• Appearance/Colour: Colourless oil
• Melting Point: 134-136℃
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 191.939 °C at 760 mmHg
• Flash Point: 69.882 °C
• PSA: 26.30000
• Density: 1.387 g/cm³
• LogP: 1.50060
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

EthylBromomethacrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: ETHYL 2-(BROMOMETHYL)ACRYLATE is an intermediate used for the synthesis of aza inhibitors of chorismate mutase. It can be employed as an electrophile for various organometallic compounds. The organometallic derivatives of the compound can be used for the synthesis of α-methylene lactones and lactams. It can also be used for the polymerization of functionalized acrylic monomers.

Technology Process of Ethyl 2-(bromomethyl)acrylate

There total 12 articles about Ethyl 2-(bromomethyl)acrylate 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: 90.0%

ethyl 2-(hydroxymethyl)acrylate (10029-04-6) → ethyl 2-bromomethyl-2-propenoate (17435-72-2)

Guidance literature:

With phosphorus tribromide; In diethyl ether; at 20 ℃; Cooling with ice;

DOI:10.1002/pola.24562

Reference yield: 75.0%

ethanol (64-17-5) + 2-(bromomethyl)acrylic acid (72707-66-5) → ethyl 2-bromomethyl-2-propenoate (17435-72-2)

Guidance literature:

With sulfuric acid; In benzene; for 72h; Heating;

DOI:10.1021/jm00384a027

Reference yield: 41.0%

ethene (74-85-1) + (1-diazo-2-ethoxy-2-oxoethyl)(2-(2-ethoxy-2-oxoethoxy)carbonylphenyl)iodonium hexafluorophosphate → ethyl 2-bromomethyl-2-propenoate (17435-72-2)

Guidance literature:

ethene; (1-diazo-2-ethoxy-2-oxoethyl)(2-(2-ethoxy-2-oxoethoxy)carbonylphenyl)iodonium hexafluorophosphate; With rhodium bis(1-adamantate) dimer; In dichloromethane; at -50 ℃; for 1.5h; Sealed tube;

With tetrabutylammomium bromide; In dichloromethane; at -50 - 20 ℃; for 10h; Sealed tube;

DOI:10.1021/jacs.9b08632

upstream raw materials:

3-Bromo-2-bromomethyl-propionic acid ethyl ester

ethanol

2-(bromomethyl)acrylic acid

ethyl 2-(hydroxymethyl)acrylate

Downstream raw materials:

5-Benzo[1,3]dioxol-5-yl-1-(4-methoxy-phenyl)-3-methylene-pyrrolidin-2-one

6,10-dimethyl-3-methylene-7,9-diphenyl-1,8-dioxaspiro<4,5>decan-2-one

4,5-dihydro-5-ethyl-3-methylene-2(3H)-furanone

α-methylenecyclohexanepropanoic acid ethyl ester

Refernces

• 1、 Nelson et al.. "". . p. 1225,1228. Retrieved 1969.
• 2、 Zhang, Lei,Drummond, Elena,Brodney, Michael A.,Cianfrogna, Julie,Drozda, Susan E.,Grimwood, Sarah,Vanase-Frawley, Michelle A.,Villalobos, Anabella. "Design, synthesis and evaluation of [3H]PF-7191, a highly specific nociceptin opioid peptide (NOP) receptor radiotracer for in vivo receptor occupancy (RO) studies". . p. 5219 - 5223. Retrieved 2014.
• 3、 He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng. "Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines". supporting information. . Retrieved 2021/05/31.
• 4、 Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying. "Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer". supporting information. p. 8575 - 8579. Retrieved 2021/11/13.