ETHYL 2-(BROMOMETHYL)ACRYLATE
- Product Name
- ETHYL 2-(BROMOMETHYL)ACRYLATE
- CAS No.
- 17435-72-2
- Chemical Name
- ETHYL 2-(BROMOMETHYL)ACRYLATE
- Synonyms
- Ethyl Bromomethacrylate;3-bromo-2-methyl-2-propenoic acid ethyl ester;DK588;NSC 215252;DKFELEX0148;2-Carbethoxyallyl Bromide;Ethyl2-(Bromomethyl)acrvlate;ETHYL 2-(BROMOMETHYL)ACRYLATE;Ethyl 2-(bromomethyl)propenoate;Ethyl 2-(bromomethyl)acrylate,97%
- CBNumber
- CB0741901
- Molecular Formula
- C6H9BrO2
- Formula Weight
- 193.04
- MOL File
- 17435-72-2.mol
ETHYL 2-(BROMOMETHYL)ACRYLATE Property
- Melting point:
- 134-136℃
- Boiling point:
- 38 °C/0.8 mmHg (lit.)
- Density
- 1.398 g/mL at 25 °C (lit.)
- refractive index
- n20/D 1.479(lit.)
- Flash point:
- 178 °F
- storage temp.
- -20°C
- solubility
- Chloroform (Sparingly), Ethyl Acetate (Slightly)
- form
- Liquid
- color
- Colorless to pale yellow
- BRN
- 970108
- InChI
- InChI=1S/C6H9BrO2/c1-3-9-6(8)5(2)4-7/h2-4H2,1H3
- InChIKey
- MTCMFVTVXAOHNQ-UHFFFAOYSA-N
- SMILES
- C(OCC)(=O)C(CBr)=C
- CAS DataBase Reference
- 17435-72-2(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 425222
- Product name
- Ethyl 2-(bromomethyl)acrylate
- Purity
- 98%
- Packaging
- 1g
- Price
- $77.2
- Updated
- 2025/07/31
- Product number
- 425222
- Product name
- Ethyl 2-(bromomethyl)acrylate
- Purity
- 98%
- Packaging
- 5g
- Price
- $246
- Updated
- 2025/07/31
- Product number
- B1820
- Product name
- Ethyl 2-(Bromomethyl)acrylate (stabilized with HQ)
- Purity
- >97.0%(GC)
- Packaging
- 1g
- Price
- $55
- Updated
- 2025/07/31
- Product number
- B1820
- Product name
- Ethyl 2-(Bromomethyl)acrylate (stabilized with HQ)
- Purity
- >97.0%(GC)
- Packaging
- 5g
- Price
- $207
- Updated
- 2025/07/31
- Product number
- E900390
- Product name
- EthylBromomethacrylate
- Packaging
- 10g
- Price
- $245
- Updated
- 2021/12/16
ETHYL 2-(BROMOMETHYL)ACRYLATE Chemical Properties,Usage,Production
Chemical Properties
Colourless Oil
Uses
ETHYL 2-(BROMOMETHYL)ACRYLATE is an intermediate used for the synthesis of aza inhibitors of chorismate mutase.
Uses
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.
General Description
Ethyl 2-(bromomethyl)acrylate is an allylic alkylating reagent.
Synthesis
10029-04-6
17435-72-2
GENERAL STEPS: Phosphorus tribromide (0.51 mL, 5.4 mmol) was added slowly and dropwise to a stirred solution of ethyl 2-hydroxymethacrylate (2 g, 15.4 mmol) in ether (15 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 3 h and subsequently warmed to room temperature. The reaction was quenched by the addition of water (5 mL) and the product was extracted with hexane (3 x 10 mL). The organic layers were combined, washed with brine (2 × 10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuum to afford ethyl 2-bromomethacrylate (2.4 g, 12.3 mmol, 82% yield) as a colorless liquid, which could be used in the next reaction without further purification. The product was characterized as follows: colorless oil; 1H NMR (400 MHz, CDCl3) δ 1.30 (t, J = 7.2 Hz, 3H, H6), 4.16 (s, 2H, H4), 4.24 (q, J = 7.0 Hz, 2H, H5), 5.92 (s, 1H, H1'), 6.30 (s, 1H, H1); 13C NMR ( 101 MHz, CDCl3) δ 14.1 (CH3, C6), 29.3 (CH2, C4), 61.2 (CH2, C5), 128.8 (CH2, C1), 137.6 (C, C2), 164.8 (C, C3); IR (νmax, cm-1) 1718 (C=O ester), 1628 (C=C alkene), 1182 (C-O ester), 523 (C-Br); HRMS-EI: m/z [M+H]+ calcd for C6H10BrO2: 192.9864, found: 192.6870.
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.]
References
[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 6, p. 1513 - 1516
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1872 - 1875
[3] Angew. Chem., 2016, vol. 128, # 5, p. 1904 - 1907,4
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 41, p. 12619 - 12623
[5] Angew. Chem., 2017, vol. 129, # 41, p. 12793 - 12797,5
ETHYL 2-(BROMOMETHYL)ACRYLATE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from ETHYL 2-(BROMOMETHYL)ACRYLATE manufacturers
- Product
- ETHYL 2-(BROMOMETHYL)ACRYLATE 17435-72-2
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-08-11
- Product
- ETHYL 2-(BROMOMETHYL)ACRYLATE 17435-72-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 100Kg
- Release date
- 2018-08-08