Ethyl 4-fluoro-3-hydroxybutanoate

Base Information

• Chemical Name: Ethyl 4-fluoro-3-hydroxybutanoate
• CAS No.: 660-47-9
• Molecular Formula: C₆H₁₁FO₃
• Molecular Weight: 150.15
• NSC Number: 24564
• DSSTox Substance ID: DTXSID80282120
• Mol file: 660-47-9.mol

Synonyms:660-47-9;ethyl 4-fluoro-3-hydroxybutanoate;NSC24564;ethyl 4-fluoranyl-3-oxidanyl-butanoate;DTXSID80282120;NSC-24564;4-fluoro-3-hydroxybutanoic acid ethyl ester;A837995

Chemical Property of Ethyl 4-fluoro-3-hydroxybutanoate

Chemical Property:

• Vapor Pressure: 0.0133mmHg at 25°C
• Boiling Point: 229.5°Cat760mmHg
• Flash Point: 92.6°C
• Density: 1.117g/cm³
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 150.06922237
• Heavy Atom Count: 10
• Complexity: 105

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(CF)O

Technology Process of Ethyl 4-fluoro-3-hydroxybutanoate

There total 3 articles about Ethyl 4-fluoro-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: 87.0%

C6H10ClFO3 (1353275-75-8) → Ethyl-4-fluor-3-hydroxybutyrat (660-47-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; Inert atmosphere; Reflux;

DOI:10.1039/c1cc15889a

Reference yield: 74.0%

ethanol (64-17-5) + 4-fluoro-3-hydroxybutyronitrile (1537-89-9) → Ethyl-4-fluor-3-hydroxybutyrat (660-47-9)

Guidance literature:

With sulfuric acid; at 80 - 85 ℃; for 22h;

DOI:10.1021/ja9042824

Reference yield:

ethyl 4-chloro-4-fluoro-3-oxobutanoate (111218-58-7) → Ethyl-4-fluor-3-hydroxybutyrat (660-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / benzene / 3.5 h / 0 - 20 °C / Inert atmosphere

2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / Inert atmosphere; Reflux

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;

DOI:10.1039/c1cc15889a

upstream raw materials:

ethanol

4-fluoro-3-hydroxybutyronitrile

ethyl 4-chloro-4-fluoro-3-oxobutanoate

C₆H₁₀ClFO₃

Refernces

• 1、 Liu, Yuan,Hazzard, Christopher,Eustaquio, Alessandra S.,Reynolds, Kevin A.,Moore, Bradley S.. "Biosynthesis of salinosporamides from α,β-unsaturated fatty acids: Implications for extending polyketide synthase diversity". supporting information; scheme or table. p. 10376 - 10377. Retrieved 2009/12/23.