(-)-Ethyl alpha-bromopropionate

Base Information

• Chemical Name: (-)-Ethyl alpha-bromopropionate
• CAS No.: 30365-54-9
• Molecular Formula: C5H9BrO2
• Molecular Weight: 181.029
• UNII: 814Q14L3IE
• Nikkaji Number: J56.910K
• Wikidata: Q27269205
• Mol file: 30365-54-9.mol

Synonyms:30365-54-9;(-)-Ethyl alpha-bromopropionate;ethyl (2S)-2-bromopropanoate;Propanoic acid, 2-bromo-, ethyl ester, (2S)-;Ethyl (S)-2-bromopropanoate;(-)-Ethyl 2-bromopropionate;(s)-ethyl 2-bromopropanoate;UNII-814Q14L3IE;814Q14L3IE;Ethyl alpha-bromopropionate, (-)-;SCHEMBL1732572;(S)-2-Bromopropionic acid ethyl ester;(-)-ETHYL .ALPHA.-BROMOPROPIONATE;ETHYL .ALPHA.-BROMOPROPIONATE, (-)-;EN300-2980195;J-520726;Q27269205

Chemical Property of (-)-Ethyl alpha-bromopropionate

Chemical Property:

• Boiling Point: 171 °C at 760 mmHg
• Flash Point: 58.4 °C
• Density: 1.413 g/cm³
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 179.97859
• Heavy Atom Count: 8
• Complexity: 82.5

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)Br
• Isomeric SMILES: CCOC(=O)[C@H](C)Br

Technology Process of (-)-Ethyl alpha-bromopropionate

There total 4 articles about (-)-Ethyl alpha-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: 93.0%

Ethyl 2-bromopropionate (535-11-5,41978-69-2) + (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione (205517-34-6) → ethyl (S)-2-bromopropionate (30365-54-9) + (R)-ethyl 2-bromopropanoate (51063-99-1) + Ethyl (3R,6S,2'S)-2'-[N,N'-bis-p-methoxybenzyl-6-isopropylpiperazine-2,5-dion-3-yl]propionoate (354118-66-4) + Ethyl (3R,6S,2'R)-2'-[N,N'-bis-p-methoxybenzyl-6-isopropylpiperazine-2,5-dion-3-yl]propionoate (354118-71-1)

Guidance literature:

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

DOI:10.1016/j.tet.2006.05.033

Reference yield:

Ethyl 2-bromopropionate (535-11-5,41978-69-2) → (S)-Ethyl lactate (687-47-8) + ethyl (S)-2-bromopropionate (30365-54-9)

Guidance literature:

With Bradyrhizobium japonicum haloalkane dehalogenase; at 21 ℃; pH=8.2; optical yield given as %ee; enantioselective reaction; Tris sulfate buffer; Resolution of racemate; Enzymatic reaction;

DOI:10.1002/anie.201001753

Reference yield:

ethanol (64-17-5) + ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate (57057-80-4) → ethyl (S)-2-bromopropionate (30365-54-9)

Guidance literature:

upstream raw materials:

ethanol

(S)-2-bromopropanoic acid

ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate

Ethyl 2-bromopropionate

Downstream raw materials:

(2R,1'R)-N-(1-Phenylethyl)alanin-ethylester

(2S,1'R)-N-(1-Phenylethyl)alanin-ethylester

ethyl 2-(1-hydroxycyclohexyl)propionate

L-alanin

Refernces

• 1、 Prokop, Zbynek,Sato, Yukari,Brezovsky, Jan,Mozga, Tomas,Chaloupkova, Radka,Koudelakova, Tana,Jerabek, Petr,Stepankova, Veronika,Natsume, Ryo,Van Leeuwen, Jan G. E.,Janssen, Dick B.,Florian, Jan,Nagata, Yuji,Senda, Toshiya,Damborsky, Jiri. "Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering". supporting information; experimental part. p. 6111 - 6115. Retrieved 2010/11/05.
• 2、 Harfenist, Morton,Hoerr, David C.,Crouch, Ronald. "Enantiospecific Synthesis of the trans-9-carbazoles". . p. 1356 - 1359. Retrieved 2007/10/02.