ETHYL 2-(BROMOMETHYL)ACRYLATE Chemical Properties

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 2810 6.1 / PGII

WGK Germany 

3

F 

10-19-23

HazardClass 

6.1

HS Code 

29161900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

ETHYL 2-(BROMOMETHYL)ACRYLATE Usage And Synthesis

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

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(17435-72-2)Related Product Information

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