(+)-Ethyl alpha-bromopropionate

Base Information

• Chemical Name: (+)-Ethyl alpha-bromopropionate
• CAS No.: 51063-99-1
• Molecular Formula: C5H9BrO2
• Molecular Weight: 181.029
• UNII: LIB5D6L75Z
• DSSTox Substance ID: DTXSID30426471
• Nikkaji Number: J56.911I
• Wikidata: Q27283001
• Mol file: 51063-99-1.mol

Synonyms:(+)-Ethyl alpha-bromopropionate;51063-99-1;Ethyl (R)-2-bromopropanoate;UNII-LIB5D6L75Z;(+)-Ethyl 2-bromopropionate;ethyl (2R)-2-bromopropanoate;Propanoic acid, 2-bromo-, ethyl ester, (2R)-;LIB5D6L75Z;Ethyl alpha-bromopropionate, (+)-;SCHEMBL1732517;DTXSID30426471;(r)-2-bromo-propionic acid ethyl ester;(+)-ETHYL .ALPHA.-BROMOPROPIONATE;[R,(+)]-2-Bromopropionic acid ethyl ester;ETHYL .ALPHA.-BROMOPROPIONATE, (+)-;Q27283001

Chemical Property of (+)-Ethyl alpha-bromopropionate

Chemical Property:

• Boiling Point: 51-75 °C(Press: 22 Torr)
• PSA: 26.30000
• Density: 1.413±0.06 g/cm3(Predicted)
• LogP: 1.33290
• 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 5 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: 85.0%

cyclohexylamine (108-91-8,157973-60-9) + Ethyl 2-bromopropionate (535-11-5,41978-69-2) → (R)-ethyl 2-bromopropanoate (51063-99-1) + (-)-N-cyclohexyl 2-bromopropanamide

Guidance literature:

With Candida antarctica lipase on accurel; In di-isopropyl ether; at 40 ℃; for 20h;

DOI:10.1016/S0968-0896(01)00006-2

Reference yield: 80.0%

benzylamine (100-46-9) + Ethyl 2-bromopropionate (535-11-5,41978-69-2) → (R)-ethyl 2-bromopropanoate (51063-99-1) + (S)-(-)-2-bromo-N-benzylpropanamide (131432-92-3)

Guidance literature:

With Candida antarctica lipase on accurel; In di-isopropyl ether; at 40 ℃; for 14h;

DOI:10.1016/S0968-0896(01)00006-2

upstream raw materials:

diethyl ether

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

ethylmagnesium bromide

cyclohexylamine

Downstream raw materials:

(S)-(-)-2-(2-methoxy-4-hydroxymethylphenoxy)propionic acid

(S)-N-<2-(3-chlorobenzamino)ethyl>alanine ethyl ester

D-Alanine

(S)-(?)-ethyl 2-phenoxypropionate

Refernces

• 1、 Azim, Abul,Sharma, Sunil K.,Olsen, Carl E.,Parmar, Virinder S.. "Lipase catalysed synthesis of optically enriched α-haloamides". . p. 1345 - 1348. Retrieved 2007/10/03.