(-)-Ethyl alpha-chloropropionate

Base Information

• Chemical Name: (-)-Ethyl alpha-chloropropionate
• CAS No.: 74497-15-7
• Molecular Formula: C5H9ClO2
• Molecular Weight: 136.578
• Hs Code.: 2915900090
• European Community (EC) Number: 838-772-3
• UNII: SQ49R2F429
• DSSTox Substance ID: DTXSID00426347
• Nikkaji Number: J1.644.177E
• Wikidata: Q27289336
• Mol file: 74497-15-7.mol

Synonyms:74497-15-7;(-)-Ethyl alpha-chloropropionate;ethyl (2S)-2-chloropropanoate;(S)-Ethyl 2-chloropropanoate;ETHYL (S)-2-CHLORO PROPIONATE;Ethyl (S)-2-chloropropionate;UNII-SQ49R2F429;(-)-Ethyl 2-chloropropionate;Ethyl L-alpha-chloropropionate;Propanoic acid, 2-chloro-, ethyl ester, (2S)-;SQ49R2F429;Ethyl alpha-chloropropionate, (-)-;(s)-2-chloro-propionic acid ethyl ester;Ethyl(S)-2-Chloro propionate;(R)-2-chloro-propionic acid ethyl ester;(S)-Ethyl2-chloropropanoate;SCHEMBL604352;ethyl ((S)-2-chloro propanoate;DTXSID00426347;AKOS006284200;(S)-2-Chloropropanoic acid ethyl ester;ETHYL L-.ALPHA.-CHLOROPROPIONATE;(-)-ETHYL .ALPHA.-CHLOROPROPIONATE;CS-0259841;ETHYL .ALPHA.-CHLOROPROPIONATE, (-)-;EN300-7427888;Q27289336

Chemical Property of (-)-Ethyl alpha-chloropropionate

Chemical Property:

• Boiling Point: 149 °C at 760 mmHg
• Flash Point: 49.5 °C
• PSA: 26.30000
• Density: 1.081 g/cm³
• LogP: 1.17680
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 136.0291072
• Heavy Atom Count: 8
• Complexity: 82.5

Purity/Quality:

99% ^*data from raw suppliers

S-2-CHLOROPROPIONIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (-)-Ethyl alpha-chloropropionate

There total 20 articles about (-)-Ethyl alpha-chloropropionate 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: 32.0%

(R)-Ethyl lactate (7699-00-5) → (L) Ethyl 2-chloropropanoate (74497-15-7)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; for 3.5h; Ambient temperature;

DOI:10.1021/jm00157a011

Reference yield:

→ (S)-Ethyl lactate (687-47-8) + (L) Ethyl 2-chloropropanoate (74497-15-7)

Guidance literature:

With hypochloric acid;

Reference yield:

(S)-Ethyl lactate (687-47-8) → (L) Ethyl 2-chloropropanoate (74497-15-7) + (R)-ethyl 2-chloropropanoate (42411-39-2)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

upstream raw materials:

ethyl 2-hydroxypropionate

(R)-Ethyl lactate

O-chlorosulfinyl-D-lactic acid ethyl ester

p-toluenesulfonyl chloride

Downstream raw materials:

ethyl (R)-2-(4-methoxyphenoxy)propanoate

(R)-2-(4-hydroxyphenoxy)propionic acid ethyl ester

(S)-2-chloropropanoic acid

(R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester

Refernces

• 1、 Zhang, Junjie,Wang, Huanxia,Ma, Yun,Wang, Youming,Zhou, Zhenghong,Tang, Chuchi. "CaF2 catalyzed SN2 type chlorodehydroxylation of chiral secondary alcohols with thionyl chloride: A practical and convenient approach for the preparation of optically active chloroalkanes". . p. 2261 - 2263. Retrieved 2013/05/09.
• 2、 Biedermann,Leon-Lomeli,Borbe,Prop. "Two stereoisomeric imidazoline derivatives: Synthesis and optical and α2-adrenoceptor activities". . p. 1183 - 1188. Retrieved 2007/10/02.