Methyl 2-bromo-2-methylpropionate

Base Information

• Chemical Name: Methyl 2-bromo-2-methylpropionate
• CAS No.: 23426-63-3
• Molecular Formula: C5H9BrO2
• Molecular Weight: 181.029
• Hs Code.: 29159000
• European Community (EC) Number: 245-657-6
• NSC Number: 406890
• UNII: 8SA4292KBM
• DSSTox Substance ID: DTXSID40177982
• Nikkaji Number: J228.961J
• Wikidata: Q72488380
• Mol file: 23426-63-3.mol

Synonyms:23426-63-3;methyl 2-bromo-2-methylpropanoate;Methyl 2-bromo-2-methylpropionate;Methyl 2-bromoisobutyrate;2-Bromo-2-methylpropionic acid methyl ester;Propanoic acid, 2-bromo-2-methyl-, methyl ester;Methyl alpha-bromoisobutyrate;8SA4292KBM;2-bromo-2-methyl-propionic acid methyl ester;EINECS 245-657-6;NSC-406890;AI3-15919;methyl2-bromoisobutyrate;alpha-Bromoisobutyric acid methyl ester;NSC406890;methyl a-bromoisobutyrate;Methyl 2-bromo-isobutyrate;Methyl 2-Bromoiso Butyrate;methyl-alpha-bromoisobutyrate;UNII-8SA4292KBM;Methyl alpha -bromoisobutyrate;SCHEMBL117832;methyl2-bromo-2-methylpropanoate;DTXSID40177982;methyl-2-bromo-2-methylpropanoate;2-Bromoisobutyric acid methyl ester;methyl 2-bromo-2-methyl-propanoate;methyl 2-bromo-2-methyl-propionate;methyl 2-bromo-2-methyl-proprionate;MFCD00017854;AKOS015899417;NSC 406890;AS-12543;2-bromo-2-methyl-propanoic acid methylester;CS-0008788;FT-0628443;2-bromo-2-methyl-propionoic acid methyl ester;D78112;EN300-109861;Methyl alpha-bromoisobutyrate, >=99.0% (GC);A816709;J-015106;J-521954;PROPIONIC ACID, 2-BROMO-2-METHYL-, METHYL ESTER

Chemical Property of Methyl 2-bromo-2-methylpropionate

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 4.77mmHg at 25°C
• Refractive Index: n20/D 1.451
• Boiling Point: 145.8 °C at760mmHg
• Flash Point: 49 °C
• PSA: 26.30000
• Density: 1.416 g/cm³
• LogP: 1.33290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 179.97859
• Heavy Atom Count: 8
• Complexity: 98.6

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-Bromo-2-methylpropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(=O)OC)Br
• Uses: Atom Transfer Radical Polymerization (ATRP) initiator that will generate a polymer with a methyl end group

Technology Process of Methyl 2-bromo-2-methylpropionate

There total 11 articles about Methyl 2-bromo-2-methylpropionate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

methanol (67-56-1) + 2-bromo-2-methylpropionic acid (2052-01-9) → 2-bromo-2-methylpropionic acid methyl ester (23426-63-3)

Guidance literature:

With sulfuric acid; for 2h; Reflux;

DOI:10.1021/acs.macromol.0c01697

Reference yield:

isobutyric Acid (79-31-2) → 2-bromo-2-methylpropionic acid methyl ester (23426-63-3)

Guidance literature:

With phosphorus; bromine; at 70 - 80 ℃; anschliessende Veresterung mit Methanol;

DOI:10.1021/ja01862a508

Reference yield:

Methyl isobutyrate (547-63-7,133320-07-7,67505-84-4) → 2-bromo-2-methylpropionic acid methyl ester (23426-63-3) + methyl 4-bromo 2,2-dimethyl butanoate (4833-99-2)

Guidance literature:

With n-butyllithium; ethylene dibromide; diisopropylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 0 ℃; for 3h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)85547-2

upstream raw materials:

methanol

2-bromo-2-methylpropionyl chloride

1,1-dimethoxy-2-methylprop-1-ene

dimethyl 2,2'-azobis(isobutyrate)

Downstream raw materials:

α-dimethylamino-isobutyric acid methyl ester

Methyl-(5-dimethylamino-3-hydroxy-3-phenyl-2.2-dimethyl)pentanoat

α-methoxyamino-isobutyric acid methyl ester

methyl 3-(4-chlorophenyl)-3-hydroxy-2,2-dimethylpropanoate

Refernces

• 1、 Hakobyan, Karen,McErlean, Christopher S. P.,Müllner, Markus. "Activating ATRP Initiators to Incorporate End-Group Modularity into Photo-RAFT Polymerization". . p. 10357 - 10365. Retrieved 2020.
• 2、 Kharade, Sujay V.,Kurata, Haruto,Bender, Aaron M.,Blobaum, Anna L.,Figueroa, Eric E.,Duran, Amanda,Kramer, Meghan,Days, Emily,Vinson, Paige,Flores, Daniel,Satlin, Lisa M.,Meiler, Jens,Weaver, C. David,Lindsley, Craig W.,Hopkins, Corey R.,Denton, Jerod S.. "Discovery, characterization, and effects on renal fluid and electrolyte excretion of the Kir4.1 potassium channel pore blocker, VU0134992". supporting information. p. 926 - 937. Retrieved 2018/08/04.