23426-63-3 Usage
Description
Methyl 2-bromo-2-methylpropionate is an organic compound that serves as a versatile chemical intermediate and initiator in various chemical reactions. It is characterized by its ability to initiate polymerization processes, particularly in the field of materials science.
Uses
Used in Polymer Synthesis:
Methyl 2-bromo-2-methylpropionate is used as an Atom Transfer Radical Polymerization (ATRP) initiator for the synthesis of polymers with a methyl end group. This application is significant because it allows for the controlled growth of polymer chains, resulting in polymers with specific properties and functionalities.
Application in the Chemical Industry:
Methyl 2-bromo-2-methylpropionate is used as a free radical initiator to participate in polymerization reactions. Its role in this process is crucial, as it helps to generate polymers with desired characteristics, such as controlled molecular weight, narrow molecular weight distribution, and well-defined end groups. This makes it a valuable tool in the development of advanced materials with applications in various industries, including automotive, electronics, and packaging.
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)
Synthesis Reference(s)
The Journal of Organic Chemistry, 43, p. 3684, 1978 DOI: 10.1021/jo00413a009
Check Digit Verification of cas no
The CAS Registry Mumber 23426-63-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,4,2 and 6 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 23426-63:
(7*2)+(6*3)+(5*4)+(4*2)+(3*6)+(2*6)+(1*3)=93
93 % 10 = 3
So 23426-63-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H9BrO2/c1-5(2,6)4(7)8-3/h1-3H3
23426-63-3Relevant articles and documents
1,2-Dibromoethane in the Synthesis of 2-Bromoesters: Bromination vs Alkylation
Ibarzo, Javier,Ortuno, Rosa M.
, p. 9825 - 9830 (1994)
1,2-Dibromoethane has been employed as an efficient brominating agent of tertiary carbanions in sterically congested molecules, allowing the stereoselective synthesis of 2-bromoesters in mild conditions and being compatible with the presence of C-C double bonds.Alkylation is the predominating process when tertiary or secondary carbanions in flexible open chains were used.An interpretation of these facts is provided.
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Gensler,W.J. et al.
, p. 4279 - 4281 (1968)
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