Methyl 2-(bromomethyl)acrylate Chemical Properties

Boiling point:

35-37 °C/1.3 mmHg (lit.)

Density 

1.489 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.490(lit.)

Flash point:

173 °F

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless to slightly brownish

BRN 

1852481

Stability:

Light Sensitive

InChI

InChI=1S/C5H7BrO2/c1-4(3-6)5(7)8-2/h1,3H2,2H3

InChIKey

CFTUQSLVERGMHL-UHFFFAOYSA-N

SMILES

C(OC)(=O)C(CBr)=C

CAS DataBase Reference

4224-69-5(CAS DataBase Reference)

NIST Chemistry Reference

Methyl 2-(bromomethyl)acrylate(4224-69-5)

EPA Substance Registry System

2-Propenoic acid, 2-(bromomethyl)-, methyl ester (4224-69-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-36-37/39-36/37/39

RIDADR 

UN 2810 6.1/PG 2

WGK Germany 

3

RTECS 

AS4900000

F 

8-10

HS Code 

29161900

MSDS

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

Methyl 2-(bromomethyl)acrylate Usage And Synthesis

Chemical Properties

Clear colorless to slightly brownish liquid

Uses

Methyl (2-bromomethyl)acrylate (MBrMA) may be used as chain transfer agents in the emulsion polymerization of methyl methacrylate (MMA) and styrene. MBrMA can undergo nucleophilic substitution of carboxylic acid to form methyl 2-(acyloxymethyl)acrylates.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 319, 1990
Synthetic Communications, 16, p. 387, 1986 DOI: 10.1080/00397918608057713

Synthesis

The general procedure for the synthesis of methyl 2-(bromomethyl)acrylate from methyl 2-(hydroxymethyl)acrylate was as follows: 10.2 g of 2-hydroxymethyl methacrylate produced in the previous step was dissolved in 150 mL of acetonitrile, followed by the slow dropwise addition of 4 mL of phosphorus tribromide. After the dropwise addition, the reaction was stirred continuously for 4 hours at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of an appropriate amount of water, followed by removal of the acetonitrile solvent by decompression distillation with a rotary evaporator. To the residue, 100 mL of water was added and extracted twice using ethyl acetate (100 mL each time). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent, resulting in 13.5 g of colorless liquid product in 86% yield.

References

[1] Tetrahedron Asymmetry, 2013, vol. 24, # 7, p. 395 - 401
[2] Patent: CN107915668, 2018, A. Location in patent: Paragraph 0018
[3] Organic Letters, 2011, vol. 13, # 15, p. 3864 - 3867
[4] Tetrahedron Letters, 2014, vol. 55, # 13, p. 2075 - 2077
[5] Chemical Communications, 2014, vol. 50, # 96, p. 15216 - 15219

Methyl 2-(bromomethyl)acrylate(4224-69-5)Related Product Information

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• Methyl methacrylate
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• Methyl 2-(chloromethyl)acrylate
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• Methyl
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