Methyl 2-(bromomethyl)acrylate
- Product Name
- Methyl 2-(bromomethyl)acrylate
- CAS No.
- 4224-69-5
- Chemical Name
- Methyl 2-(bromomethyl)acrylate
- Synonyms
- 2-BROMOMETHYL METHYL ACRYLATE;METHYL 2-(BROMOMETHYL)ACRYLATE;Methyl 2-(bromomethyl)propenoate;Methyl2-(Bromomethyl)acrylate>methyl2-(bromomethyl)-2-propenoate;Methyl 2-(bromomethyl)acrylate,96%;METHYL 2-(BROMOMETHYL)PROP-2-ENOATE;2-(bromomethyl)-acrylicacimethylester;Methyl 2-(broMoMethyl)acrylate, 96% 5GR;α-(Bromomethyl)acrylic acid methyl ester
- CBNumber
- CB5470370
- Molecular Formula
- C5H7BrO2
- Formula Weight
- 179.01
- MOL File
- 4224-69-5.mol
Methyl 2-(bromomethyl)acrylate Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H315Causes skin irritation
H318Causes serious eye damage
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
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
- 302546
- Product name
- Methyl 2-(bromomethyl)acrylate
- Purity
- 97%
- Packaging
- 1g
- Price
- $207
- Updated
- 2023/01/07
- Product number
- 302546
- Product name
- Methyl 2-(bromomethyl)acrylate
- Purity
- 97%
- Packaging
- 5g
- Price
- $648
- Updated
- 2023/01/07
- Product number
- M2067
- Product name
- Methyl 2-(Bromomethyl)acrylate
- Purity
- >97.0%(GC)
- Packaging
- 1g
- Price
- $28
- Updated
- 2025/07/31
- Product number
- M2067
- Product name
- Methyl 2-(Bromomethyl)acrylate
- Purity
- >97.0%(GC)
- Packaging
- 5g
- Price
- $102
- Updated
- 2025/07/31
- Product number
- M296068
- Product name
- Methyl 2-(bromomethyl)acrylate
- Packaging
- 10g
- Price
- $165
- Updated
- 2021/12/16
Methyl 2-(bromomethyl)acrylate Chemical Properties,Usage,Production
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
15484-46-5
4224-69-5
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 Preparation Products And Raw materials
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View Lastest Price from Methyl 2-(bromomethyl)acrylate manufacturers
- Product
- Methyl 2-(bromomethyl)acrylate 4224-69-5
- Price
- US $3.90-5.90/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2025-06-13
- Product
- Methyl 2-(bromomethyl)acrylate 4224-69-5
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-10-14
- Product
- Methyl 2-(bromomethyl)acrylate 4224-69-5
- Price
- US $30.00-90.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200000KG
- Release date
- 2024-08-13