Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate

Base Information

• Chemical Name: Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate
• CAS No.: 90866-33-4
• Molecular Formula: C₆H₁₁ClO₃
• Molecular Weight: 166.605
• Hs Code.: 29181990
• European Community (EC) Number: 626-176-4
• UNII: ZL59XVD2RW
• DSSTox Substance ID: DTXSID20370313
• Nikkaji Number: J455.988F
• Wikidata: Q72473629
• Mol file: 90866-33-4.mol

Synonyms:90866-33-4;Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate;(R)-Ethyl 4-chloro-3-hydroxybutanoate;ethyl (3R)-4-chloro-3-hydroxybutanoate;Ethyl (R)-(+)-4-chloro-3-hydroxybutanoate;(R)-4-Chloro-3-hydroxybutyric Acid Ethyl Ester;Butanoic acid, 4-chloro-3-hydroxy-, ethyl ester, (3R)-;Ethyl (R)-4-Chloro-3-hydroxybutyrate;(r)-4-chloro-3-hydroxybutanoic acid ethyl ester;(R)-4-Chloro-3-hydroxy-n-butyric Acid Ethyl Ester;Ethyl(S)-(-)-4-chloro-3-hydroxybutyrate;MFCD00211242;ethyl (r)-4-chloro-3-hydroxybutanoate;ZL59XVD2RW;SCHEMBL96009;DTXSID20370313;ZAJNMXDBJKCCAT-RXMQYKEDSA-N;BCP23440;ethyl-4-chloro-3(R)-hydroxybutyrate;(R)-Ethyl4-chloro-3-hydroxybutanoate;AKOS007930015;(+)-Ethyl 4-chloro-3-hydroxybutyrate;AC-5620;AM81437;CS-W010802;AC-32125;AS-14909;ethyl (+) (R)-4-chloro-3-hydroxybutyrate;C1733;Ethyl (3R)-(+)-4-Chloro-3-hvdroxybutyrate;EN300-102988;Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate, 96%;(R)-(+)-ETHYL-4-CHLORO 3-HYDROXYBUTANOATE;4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-;Butanoic acid, 4-chloro-3-hydroxy-, ethyl ester, (R)-

Chemical Property of Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.00145mmHg at 25°C
• Melting Point: 93-95 °C
• Refractive Index: 1.453
• Boiling Point: 263.4 °C at 760 mmHg
• PKA: 13.23±0.20(Predicted)
• Flash Point: 113.1 °C
• PSA: 46.53000
• Density: 1.187 g/cm³
• LogP: 0.53930
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• 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:

98% ^*data from raw suppliers

(R)-Ethyl4-Chloro-3-hydroxybutanoate(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-36-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(CCl)O
• Isomeric SMILES: CCOC(=O)C[C@H](CCl)O
• Uses: Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate is a chiral building block that can be used:To prepare allyl stannane, a precursor for the total synthesis of macrolide iriomoteolide-1b.As a starting material for the synthesis of a chiral g-αmino acid fragment, which in turn is used to prepare the immunosuppressive agent FR252921.

Technology Process of Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate

There total 36 articles about Ethyl (R)-(+)-4-chloro-3-hydroxybutyrate 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、 -. "Method for continuously preparing (R)-4-halo-3-hydroxy-butyrate by using micro-reaction system". Paragraph 0071-0093. . Retrieved 2021/02/10.
• 2、 Baumer, Benedikt,Classen, Thomas,Pohl, Martina,Pietruszka, J?rg. "Efficient Nicotinamide Adenine Dinucleotide Phosphate [NADP(H)] Recycling in Closed-Loop Continuous Flow Biocatalysis". supporting information. p. 2894 - 2901. Retrieved 2020/04/15.