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Methyl 2-bromo-2-methylpropionate

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Methyl 2-bromo-2-methylpropionate Basic information

Product Name:
Methyl 2-bromo-2-methylpropionate
Synonyms:
  • Methyl Alpha-Bromobutyrate
  • METHYL ALPHA-BROMOISOBUTYRATE
  • methyl a-bromobutyrate
  • METHYL A-BROMOISOBUTYRATE
  • METHYL 2-BROMOISOBUTYRATE
  • METHYL-2-BROMO-ISOBUTYRIC ACID
  • METHYL 2-BROMO-2-METHYLPROPIONATE
  • alpha-Bromoisobutyric acid methyl ester
CAS:
23426-63-3
MF:
C5H9BrO2
MW:
181.03
EINECS:
245-657-6
Product Categories:
  • ATRP
  • ATRP Initiators
  • Building Blocks
  • C2 to C5
  • Carbonyl Compounds
  • Chemical Synthesis
  • Acids and Derivatives
  • Esters
  • Materials Science
  • Organic Building Blocks
  • Polymer Science
  • Reagents for Controlled Radical Polymerization
  • Reagents for Polymerization
  • bc0001
Mol File:
23426-63-3.mol
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Methyl 2-bromo-2-methylpropionate Chemical Properties

Boiling point:
52 °C(Press: 19 Torr)
Density 
1.399 g/mL at 20 °C(lit.)
refractive index 
n20/D 1.451
Flash point:
49 °C
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Oil
color 
Colourless
BRN 
1209484
InChIKey
PQUSVJVVRXWKDG-UHFFFAOYSA-N
CAS DataBase Reference
23426-63-3(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
10-36/37/38
Safety Statements 
26-36
RIDADR 
UN 2929 6.1/PG 2
WGK Germany 
3
19
HS Code 
29159000

MSDS

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Methyl 2-bromo-2-methylpropionate Usage And Synthesis

Synthesis

Bromoisobutyric acid (4.17 g, 25 mmol) was dissolved in a solution of concentrated sulfuric acid (0.75 mL) and methanol (50 mL) and stirred under reflux for 2 h. The solution was then cooled to room temperature and concentrated under vacuum. The residue was dissolved in diethyl ether and washed with 10% aqueous sodium bicarbonate, washed with brine, dried under magnesium sulfate, and concentrated again under vacuum. A colorless oil was obtained (4.2 g, 23 mmol, 93% yield) 1H NMR (300 MHz, CDCl3) δ(ppm): 3.78 (s, 3H), 1.93 (s, 6H) 

Uses

Atom Transfer Radical Polymerization (ATRP) initiator that will generate a polymer with a methyl end group

Application

Methyl 2-bromo-2-methylpropionate can be used as a free radical initiator to participate in polymerization reactions.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 3684, 1978 DOI: 10.1021/jo00413a009

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