Methyl 2-bromopropionate

Base Information

• Chemical Name: Methyl 2-bromopropionate
• CAS No.: 5445-17-0
• Deprecated CAS: 57885-43-5
• Molecular Formula: C4H7BrO2
• Molecular Weight: 167.002
• Hs Code.: 29159080
• European Community (EC) Number: 226-642-3
• NSC Number: 21973
• DSSTox Substance ID: DTXSID90884159
• Nikkaji Number: J125.368I
• Mol file: 5445-17-0.mol

Synonyms:Methyl 2-bromopropionate;5445-17-0;Methyl 2-bromopropanoate;Propanoic acid, 2-bromo-, methyl ester;Methyl dl-2-bromopropionate;2-Bromopropionic acid methyl ester;Methyl alpha-bromopropionate;Methyl .alpha.-bromopropionate;methyl 2-bromo-propionate;Propionic acid, 2-bromo-, methyl ester;METHYL-2-BROMOPROPIONATE;EINECS 226-642-3;NSC 21973;1398065-68-3;methyl2-bromopropionate;(S)-methyl 2-bromopropanoate;methyl bromopropanoate;methyl bromopropionate;[R,(+)]-2-Bromopropanoic acid methyl ester;methyl2-bromopropanoate;methyl 2-brompropanoate;methyl-2-bromopropanoate;methyl 2-bromoproprionate;methyl-2-bromo-propionate;methyl 2-methyl-bromoacetate;SCHEMBL36713;methyl DL-2-bromo-propionate;rac. methyl 2-bromopropionate;2-Bromopropionicacidmethylester;methyl (RS)-2-bromopropionate;Methyl 2-bromopropionate, 98%;DTXSID90884159;Methyl (+/-)-2-bromopropionate;2-Bromopropanoic acid methyl ester;2-bromo propionic acid methyl ester;2-bromo-propionic acid methyl ester;AMY21873;BCP29092;BCP29093;NSC21973;MFCD00000143;NSC-21973;STK399903;alpha-bromopropionic acid methyl ester;AKOS003808767;BP-20549;BS-17120;B1460;CS-0154978;FT-0611607;FT-0693520;Methyl 2-bromopropionate, analytical standard;EN300-17638;Methyl(+/-)-2-Bromopropionate-2,3,3,3-d4;METHYL-2-BROMOPROPIONATE, 1000MG, NEAT;W-105625;Propanoic acid, 2-bromo-, methyl ester, (.+/-.)-;F2190-0283;Methyl (2S)-2-bromopropanoate pound>>Propanoic acid, 2-bromo-, methyl ester, (2S)-;57885-43-5

Chemical Property of Methyl 2-bromopropionate

Chemical Property:

• Appearance/Colour: clear colourless to slightly yellow liquid
• Vapor Pressure: 4.76mmHg at 25°C
• Melting Point: 177-180 °C(Solv: water (7732-18-5))
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 145.9 °C at 760 mmHg
• Flash Point: 47.1 °C
• PSA: 26.30000
• Density: 1.496 g/cm³
• LogP: 0.94280
• Storage Temp.: Flammables area
• Solubility.: water: insoluble
• Water Solubility.: Immiscible
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 165.96294
• Heavy Atom Count: 7
• Complexity: 72.1

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 2-Bromopropionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: C,Xi
• Statements: 10-34-36/37-36/37/38
• Safety Statements: 16-26-27-36/37/39-45-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CC(C(=O)OC)Br
• Uses: Methyl 2-bromopropionate was used as initiator during the synthesis of polymer brushes with single-walled carbon nanotubes as backbones. It was used as starting reagent for the synthesis of 2-18F-fluoropropionic acid, positron emission tomography imaging agent for prostate cancer.

Technology Process of Methyl 2-bromopropionate

There total 22 articles about Methyl 2-bromopropionate 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: 99.0%

methanol (67-56-1) + (S)-2-bromopropionyl chloride (7148-74-5,52152-04-2,71425-59-7,22592-73-0) → methyl (2S)-2-bromopropanoate (20047-41-0,57885-43-5,5445-17-0,62076-23-7)

Guidance literature:

With pyridine; In chloroform; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ja107197p

Reference yield: 96.7%

3-Bromopropionic acid (590-92-1) + methyl D-lactate chlorosulfite → methyl (2S)-2-bromopropanoate (20047-41-0,57885-43-5,5445-17-0,62076-23-7)

Guidance literature:

With hydrogenchloride; hydrogen bromide; In water;

Reference yield: 87.0%

Methyl 2-bromopropionate (5445-17-0) + (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione (205517-34-6) → methyl (2S)-2-bromopropanoate (20047-41-0,57885-43-5,5445-17-0,62076-23-7) + (2R)-methyl 2-bromopropionate (20047-41-0) + (S)-2-[(2R,5S)-5-Isopropyl-1,4-bis-(4-methoxy-benzyl)-3,6-dioxo-piperazin-2-yl]-propionic acid methyl ester + (R)-2-[(2R,5S)-5-Isopropyl-1,4-bis-(4-methoxy-benzyl)-3,6-dioxo-piperazin-2-yl]-propionic acid methyl ester

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tet.2006.05.033

upstream raw materials:

methanol

α-bromopropionyl bromide

2-Bromopropionic acid

propionyl chloride

Downstream raw materials:

2-phenoxypropionic acid

methyl 2-methoxypropionate

methyl 2-phenoxypropanoate

methyl 2-(1,3-dioxoisoindolin-2-yl)propanoate

Refernces

• 1、 Iwamoto, Takahiro,Okuzono, Chiemi,Adak, Laksmikanta,Jin, Masayoshi,Nakamura, Masaharu. "Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides". supporting information. p. 1128 - 1131. Retrieved 2019/01/28.
• 2、 Mao, Jianyou,Liu, Feipeng,Wang, Min,Wu, Lin,Zheng, Bing,Liu, Shangzhong,Zhong, Jiangchun,Bian, Qinghua,Walsh, Patrick J.. "Cobalt-bisoxazoline-catalyzed asymmetric kumada cross-coupling of racemic α-bromo esters with aryl grignard reagents". supporting information. p. 17662 - 17668. Retrieved 2015/02/02.