Ethyl 4-chloro-3-hydroxybutanoate

Base Information

• Chemical Name: Ethyl 4-chloro-3-hydroxybutanoate
• CAS No.: 10488-69-4
• Molecular Formula: C₆H₁₁ClO₃
• Molecular Weight: 166.605
• Hs Code.: 2918199090
• European Community (EC) Number: 838-603-3
• DSSTox Substance ID: DTXSID90402594
• Nikkaji Number: J879.289E
• Mol file: 10488-69-4.mol

Synonyms:4-chloro-3-hydroxybutyric acid ethyl ester;CHBE;ethyl 4-chloro-3-hydroxybutanoate

Chemical Property of Ethyl 4-chloro-3-hydroxybutanoate

Chemical Property:

• Vapor Pressure: 0.00145mmHg at 25°C
• Melting Point: 136 °C
• Refractive Index: 1.453
• Boiling Point: 263.44 °C at 760 mmHg
• PKA: 13.23±0.20(Predicted)
• Flash Point: 113.125 °C
• PSA: 46.53000
• Density: 1.187 g/cm³
• LogP: 0.53930
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 166.0396719
• Heavy Atom Count: 10
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

Ethyl4-Chloro-3-hydroxybutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R41:
• Hazard Codes: Xi:Irritant
• Statements: R41:
• Safety Statements: S26:; S39:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(CCl)O

Technology Process of Ethyl 4-chloro-3-hydroxybutanoate

There total 36 articles about Ethyl 4-chloro-3-hydroxybutanoate 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: 100.0%

ethyl (2-chloroaceto)acetate (638-07-3) → ethyl (S)-4-chloro-3-hydroxybutanoate (10488-69-4,86728-85-0,87068-18-6,90866-33-4)

Guidance literature:

With formic acid; NAD; sodium formate; formate dehydrogenase; In water; at 30 ℃; for 3.5h; pH=6.5;

DOI:10.1271/bbb.69.544

Reference yield: 99.0%

ethyl (2-chloroaceto)acetate (638-07-3) → ethyl (L)-4-chloro-3-hydroxybutyrate (10488-69-4,86728-85-0,87068-18-6,90866-33-4)

Guidance literature:

With D-glucose; β-keto ester reductase L-1; tris hydrochloride; NADPH; at 30 ℃; for 48h; relative reaction rate; other β-keto esters; var. time;

DOI:10.1246/bcsj.67.524

Reference yield: 93.0%

ethanol (64-17-5) + (S)-4-chloro-3-hydroxy butyronitrile (127913-44-4,637-75-2) → ethyl (S)-4-chloro-3-hydroxybutanoate (10488-69-4,86728-85-0,87068-18-6,90866-33-4)

Guidance literature:

With hydrogenchloride;

DOI:10.2174/157017812802139654

upstream raw materials:

4-chloro-3-hydroxybutyronitrile

ethanol

carbon monoxide

epichlorohydrin

Downstream raw materials:

(R)-4-cyano-3-hydroxybutyric acid,ethyl ester

(2E)-4-hydroxybut-2-enoic acid

(E)-ethyl 4-hydroxybut-2-enoate

ethyl (E)-4-chlorobut-2-enoate

Refernces

• 1、 Trost, Barry M.,Hanson, Paul R.. "A practical asymmetric synthesis of a 1,7-enyne A-ring synthon en route toward the total synthesis of vitamin D3 analogues". . p. 8119 - 8122. Retrieved 1994.
• 2、 Nakamura, Kaoru,Kawai, Yasushi,Oka, Shinzaburo,Ohno, Atsuyoshi. "A NEW METHOD FOR STEREOCHEMICAL CONTROL OF MICROBIAL REDUCTION. REDUCTION OF β-KETO ESTERS WITH BAKERS' YEAST IMMOBILIZED BY MAGNESIUM ALGINATE". . p. 2245 - 2246. Retrieved 1989.
• 3、 Garcia, Maria Jesus,Rebolledo, Francisca,Gotor, Vicente. "Practical Enzymatic Route to Optically Active 3-Hydroxyamides. Synthesis of 1,3-Aminoalcohols". . p. 2199 - 2210. Retrieved 1993.
• 4、 Sakaki,Sakoda,Sugita,Sato,Kaneko. "Lipase-catalyzed asymmetric synthesis of 6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-ones and their conversion to chiral 5,6-epoxyhexanoates". . p. 343 - 346. Retrieved 1991.
• 5、 Nakamura, Kaoru,Kawai, Yasushi,Oka, Shinzaburo,Ohno, Atsuyoshi. "Stereochemical Control in Microbial Reduction. 8. Stereochemical Control in Microbial Reduction of β-Keto Esters". . p. 875 - 879. Retrieved 1989.
• 6、 Jung, Jihye,Park, Seongsoon,Kim, Hyung Kwoun. "Synthesis of a chiral alcohol using a rationally designed Saccharomyces cerevisiae reductase and a NADH cofactor regeneration system". . p. 15 - 21. Retrieved 2012.
• 7、 Jung, Jihye,Park, Hyun Joo,Uhm, Ki-Nam,Kim, Dooil,Kim, Hyung-Kwoun. "Asymmetric synthesis of (S)-ethyl-4-chloro-3-hydroxy butanoate using a Saccharomyces cerevisiae reductase: Enantioselectivity and enzyme-substrate docking studies". . p. 1841 - 1849. Retrieved 2010.
• 8、 Bertau,Buerli,Hungerbuehler,Wagner. "A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones". . p. 2103 - 2107. Retrieved 2001.
• 9、 Yasohara, Yoshihiko,Kizaki, Noriyuki,Hasegawa, Junzo,Wada, Masaru,Kataoka, Michihiko,Shimizu, Sakayu. "Molecular Cloning and Overexpression of the Gene Encoding an NADPH-Dependent Carbonyl Reductase from Candida magnoliae, Involved in Stereoselective Reduction of Ethyl 4-Chloro-3-oxobutanoate". . p. 1430 - 1436. Retrieved 2000.
• 10、 Wang, Ya-Jun,Liu, Xiao-Qing,Luo, Xi,Liu, Zhi-Qiang,Zheng, Yu-Guo. "Cloning, expression and enzymatic characterization of an aldo-keto reductase from Candida albicans XP1463". . p. 44 - 50. Retrieved 2015.