17435-72-2

Basic information

• Product Name: ETHYL 2-(BROMOMETHYL)ACRYLATE
• Synonyms: 2-(BROMOMETHYL)ACRYLIC ACID ETHYL ESTER;ETHYL 2-(BROMOMETHYL)ACRYLATE;2-Propenoic acid, 2-(bromomethyl)-, ethyl ester;2-(Bromomethyl)-2-propenoic Acid Ethyl Ester;2-Carbethoxyallyl Bromide;Ethyl 2-(Bromomethyl)-2-propenoate;Ethyl 3-Bromo-2-(methylene)propanoate;Ethyl Bromomethacrylate
• CAS NO: 17435-72-2
• Molecular Formula: C₆H₉BrO₂
• Molecular Weight: 193.04
• EINECS: 1533716-785-6
• Product Categories: All Aliphatics;Aliphatics;AcrylateCarbonyl Compounds;Acrylic Monomers;C6 to C7;Esters;Monomers;NULL;Benzothiophenes ,Thiophenes
• Mol File: 17435-72-2.mol
• Article Data: 46

Chemical Properties

• Melting Point: 134-136℃
• Boiling Point: 38 °C0.8 mm Hg(lit.)
• Flash Point: 178 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.398 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• BRN: 970108
• CAS DataBase Reference: ETHYL 2-(BROMOMETHYL)ACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-(BROMOMETHYL)ACRYLATE(17435-72-2)
• EPA Substance Registry System: ETHYL 2-(BROMOMETHYL)ACRYLATE(17435-72-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2810 6.1 / PGII
• WGK Germany: 3
• F: 10-19-23
• Hazardous Substances Data: 17435-72-2(Hazardous Substances Data)

Usage

Chemical Description

Ethyl 2-(bromomethyl)acrylate is an organic compound used in organic synthesis.

Description

Ethyl 2-(bromomethyl)acrylate is an allylic alkylating reagent, characterized as a colorless oil. It serves as a versatile intermediate in the synthesis of various compounds, particularly in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
Ethyl 2-(bromomethyl)acrylate is used as an intermediate for the synthesis of aza inhibitors of chorismate mutase, which are important in the development of novel drugs targeting specific enzyme pathways.
Used in Chemical Synthesis:
Ethyl 2-(bromomethyl)acrylate is 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, which are valuable building blocks in organic chemistry.
Used in Polymer Science:
Ethyl 2-(bromomethyl)acrylate can also be used for the polymerization of functionalized acrylic monomers, contributing to the development of new materials with specific properties for various applications.

Purification Methods

If it contains some free acid, add H2O, cool, and neutralise with NaHCO3 until evolution of CO2 ceases. Extract the mixture with Et2O (3x) and dry the combined extracts (Na2SO4, 3hours). Evaporate Et2O and distil the ester collecting fraction b 39-40o/0.9mm and check spectra. [Preparation and NMR: Ramarajan et al. Org Synth Coll Vol VII 211 1990, Beilstein 2 IV 1541.]

Upstream product

• 58539-11-0 3-Bromo-2-bromomethyl-propionic acid ethyl ester 
• 105-53-3 diethyl malonate 
• 64-17-5 ethanol 
• 72707-66-5 2-(bromomethyl)acrylic acid 
• 20605-01-0 diethyl bis(hydroxymethyl)malonate 
• 140-88-5 ethyl acrylate 
• 50-00-0 formaldehyd 
• 74-85-1 ethene 
• 7789-60-8 phosphorus tribromide 
• 10029-04-6 ethyl 2-(hydroxymethyl)acrylate 

Downstream Products

• 54312-36-6 methylene-2 (oxo-2 cyclohexane)yl-3 propionate d'ethyle 
• 77547-07-0 γ-benzyl-α-methylene-γ-butyrolactone 
• 91546-55-3 3-methylene-cis-8-benzyl-1-oxa-8-azaspiro<4.5>decan-2-one 
• 126812-35-9 6,10-dimethyl-3-methylene-7,9-diphenyl-1,8-dioxaspiro<4,5>decan-2-one 
• 98351-65-6 3-methylene-1,5-diphenyl-2-pyrrolidinone 
• 125216-69-5 1-(4-methoxyphenyl)-3-methylene-5-phenylpyrrolidin-2-one 
• 134486-62-7 9-Hydroxy-2-methylene-9-phenyl-nonanoic acid ethyl ester 
• 26613-71-8 4-phenyl-2-methylenebutyrolactone 
• 32670-57-8 2,5-Dimethylen-1,6-hexadisaeurediethylester 
• 109907-81-5 ethyl 4-hydroxy-2-methylene-4-phenylbutanoate 
• 62873-16-9 5-methyl-3-(methylidene)dihydrofuran-2(5H)-one 
• 67964-41-4 4,5-dihydro-5-ethyl-3-methylene-2(3H)-furanone 
• 67464-50-0 3-Methylen-8c-tert.butyl-(5rO¹)-1-oxa-spiro<4,5>decan-2-on 
• 67464-47-5 cis-8-tert-butyl-3-methylene-1-oxaspiro<4.5>decan-2-one 

Relevant articles and documents

A new end group structure of poly(ethylene glycol) for hydrolysis-resistant biomaterials

A new PEG end-group structure (α-PEG-MA) was designed and synthesized. When compared with the conventionally used PEG-acrylate structure, the vinyl group in the new structure showed comparable reactivity in thiol-ene reactions, but the formed materials were hydrolysis resistant because there is no ester linkage in the backbone chains. Copyright

An efficient and simple strategy toward the synthesis of highly functionalized compounds

The expedient syntheses of small libraries of ((β-ethoxycarbonyl, -cyano and -acetyl)propyloxy) methylphosphonate scaffolds bearing olefin, sulfanyl, or amine functions are described. All these new derivatives are readily produced from easily available starting reagents (aldehydes, electron-poor olefins, and dialkylphosphites) following a three steps reaction sequence of condensations, SN2′-type reaction and a conjugated thia- or aza-Michael 1,4-addition with aromatic and aliphatic thiol or amine nucleophiles.

Catalytic Cleavage of C(sp2)-C(sp2) Bonds with Rh-Carbynoids

We report a catalytic strategy that generates rhodium-carbynoids by selective diazo activation of designed carbyne sources. We found that rhodium-carbynoid species provoke C(sp2)-C(sp2) bond scission in alkenes by inserting a monovalent carbon unit between both sp2-hybridized carbons. This skeletal remodeling process accesses synthetically useful allyl cation intermediates that conduct to valuable allylic building blocks upon nucleophile attack. Our results rely on the formation of cyclopropyl-I(III) intermediates able to undergo electrocyclic ring-opening, following the Woodward-Hoffmann-DePuy rules.