Ethyl (S)-4-cyano-3-hydroxybutyrate

Base Information

• Chemical Name: Ethyl (S)-4-cyano-3-hydroxybutyrate
• CAS No.: 312745-91-8
• Molecular Formula: C7H11NO3
• Molecular Weight: 157.169
• Hs Code.: 2942000000
• DSSTox Substance ID: DTXSID10427305
• Nikkaji Number: J2.602.518D
• Wikidata: Q72473915
• Mol file: 312745-91-8.mol

Synonyms:312745-91-8;Ethyl (S)-4-cyano-3-hydroxybutyrate;(S)-Ethyl 4-cyano-3-hydroxybutanoate;ethyl (3S)-4-cyano-3-hydroxybutanoate;Ethyl S-(+)-4-Cyano-3-hydroxybutyrate;Ethyl(S)-4-cyano-3-hydroxybutyrate;(S)-ETHYL-4-CYANO-3-HYDROXYBUTYRATE;Butanoic acid, 4-cyano-3-hydroxy-, ethyl ester, (3S)-;MFCD00672878;Ethyl (S)-(+)-4-cyano-3-hydroxybutyrate;SCHEMBL395418;DTXSID10427305;AKOS006237892;CS-W016222;Ethyl (S)-4-Cyano-3-Hydroxy Butyrate;AS-62177;A5663;EN300-93586;(S)-3-Hydroxy-4-cyanobutanoic acid ethyl ester;J-018353

Chemical Property of Ethyl (S)-4-cyano-3-hydroxybutyrate

Chemical Property:

• Vapor Pressure: 1.75E-05mmHg at 25°C
• Refractive Index: 1.4480
• Boiling Point: 325.6 °C at 760 mmHg
• PKA: 13.03±0.20(Predicted)
• Flash Point: 150.7 °C
• PSA: 70.32000
• Density: 1.132 g/cm³
• LogP: 0.21418
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol (Slightly)
• Water Solubility.: Not miscible or difficult to mix with water.
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 157.07389321
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

98% ^*data from raw suppliers

EthylS-(+)-4-Cyano-3-hydroxybutyrate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(CC#N)O
• Isomeric SMILES: CCOC(=O)C[C@H](CC#N)O
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of Ethyl (S)-4-cyano-3-hydroxybutyrate

There total 5 articles about Ethyl (S)-4-cyano-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: 90.0%

(S)-3-hydroxyglutaric acid monoamidemonoethyl ester → (S)-3-hydroxy-4-cyanobutyric acid ethyl ester (312745-91-8)

Guidance literature:

With pyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; at 20 ℃; for 96h;

DOI:10.1016/j.tetasy.2004.04.007

Reference yield:

sodium cyanide (773837-37-9) + ethyl (2-chloroaceto)acetate (638-07-3) → (R)-ethyl 4-cyano-3-hydroxybutyrate (141942-85-0) + (S)-3-hydroxy-4-cyanobutyric acid ethyl ester (312745-91-8)

Guidance literature:

With vector pCDFDuet-HF and vector pET₃₀-(S)-alcohol dehydrogenase in Escherichia coli BL₂₁(DE₃); In aq. buffer; at 30 ℃; for 10h; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.201300549

Reference yield:

ethanol (64-17-5) + (R)-3-hydroxy-4-cyano-butyric acid (287955-93-5) → (R)-ethyl 4-cyano-3-hydroxybutyrate (141942-85-0) + (S)-3-hydroxy-4-cyanobutyric acid ethyl ester (312745-91-8)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 0.5h; Title compound not separated from byproducts.;

DOI:10.1021/ja0259842

upstream raw materials:

ethanol

(R)-3-hydroxy-4-cyano-butyric acid

diethyl 3-hydroxyglutarate

3-hydroxyglutaronitrile

Refernces

• 1、 Dong, Fangyuan,Chen, Hui,Malapit, Christian A.,Prater, Matthew B.,Li, Min,Yuan, Mengwei,Lim, Koun,Minteer, Shelley D.. "Biphasic Bioelectrocatalytic Synthesis of Chiral β-Hydroxy Nitriles". supporting information. p. 8374 - 8382. Retrieved 2020/05/22.
• 2、 DeSantis, Grace,Zhu, Zuolin,Greenberg, William A.,Wong, Kelvin,Chaplin, Jenny,Hanson, Sarah R.,Farwell, Bob,Nicholson, Lawrence W.,Rand, Cynthia L.,Weiner, David P.,Robertson, Dan E.,Burk, Mark J.. "An enzyme library approach to biocatalysis: Development of nitrilases for enantioselective production of carboxylic acid derivatives". . p. 9024 - 9025. Retrieved 2007/10/03.