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Methyl 2-bromo-2-methylpropionate

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Methyl 2-bromo-2-methylpropionate Basic information
Synthesis
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;Esters;Materials Science;Organic Building Blocks;Polymer Science;Reagents for Controlled Radical Polymerization;Reagents for Polymerization;Acids and Derivatives;bc0001
Mol File:23426-63-3.mol
Methyl 2-bromo-2-methylpropionate Structure
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
Fp 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
InChIKeyPQUSVJVVRXWKDG-UHFFFAOYSA-N
CAS DataBase Reference23426-63-3(CAS DataBase Reference)
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 Information
ProviderLanguage
SigmaAldrich English
Methyl 2-bromo-2-methylpropionate Usage And Synthesis
SynthesisBromoisobutyric 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) 
	Methyl 2-bromo-2-methylpropionate
UsesAtom Transfer Radical Polymerization (ATRP) initiator that will generate a polymer with a methyl end group
ApplicationMethyl 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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