(S)-(+)-Glycidyl butyrate

Base Information

• Chemical Name: (S)-(+)-Glycidyl butyrate
• CAS No.: 65031-96-1
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• Hs Code.: 29156000
• DSSTox Substance ID: DTXSID30426451
• Nikkaji Number: J627.649K
• Wikidata: Q72480663
• Mol file: 65031-96-1.mol

Synonyms:65031-96-1;(S)-(+)-Glycidyl butyrate;(s)-Glycidyl Butyrate;(S)-Oxiran-2-ylmethyl butyrate;[(2S)-oxiran-2-yl]methyl butanoate;Butanoic acid, (2S)-oxiranylmethyl ester;Butyric Acid (S)-Glycidyl Ester;MFCD00273369;Butanoic acid (2s)-2-oxiranylmethyl ester;(S)-Glycidylbutyrate;SCHEMBL78536;(S)-Oxiran-2-ylmethylbutyrate;(S)-2-(Butyryloxymethyl)oxirane;DTXSID30426451;YLNSNVGRSIOCEU-LURJTMIESA-N;(S)-(+)-Glycidyl butyrate, 98%;AKOS005259912;AKOS015892752;BS-43780;CS-0135409;G0283;F20484;A851383;((S)-oxiran-2-yl)methyl butyrate;(S)-Glycidyl Butyrate

Chemical Property of (S)-(+)-Glycidyl butyrate

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Refractive Index: 1.428
• Boiling Point: 196.3 °C at 760 mmHg
• Flash Point: 85 °C
• PSA: 38.83000
• Density: 1.069 g/cm³
• LogP: 0.72850
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

(S)-OxiranylmethylButyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)OCC1CO1
• Isomeric SMILES: CCCC(=O)OC[C@@H]1CO1
• Uses: (S)-Oxiranylmethyl Butyrate is the enantiomer of (2R)-2-Oxiranylmethyl Ester Butanoic Acid (O847090), which is a reagent used in the synthesis of glycidol, a stabilizer in manufacturing of vinyl polymers; intermediate in the synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraulic fluids; epoxy resin diluent.

Technology Process of (S)-(+)-Glycidyl butyrate

There total 3 articles about (S)-(+)-Glycidyl butyrate 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: 45.0%

(+/-)-glycidyl butyrate (2461-40-7) → butyric acid-3-chloro-(S)-2-hydroxy-propyl ester (890051-54-4) + butyric acid-3-chloro-(R)-2-hydroxy-propyl ester (890051-57-7) + (R)-glycidyl butyrate (60456-26-0) + (S)-glycidyl butyrate (65031-96-1)

Guidance literature:

With hydrogenchloride; (R,R)-[Co(salen)]2*GaCl₃; In diethyl ether; at 0 - 4 ℃; for 4h;

DOI:10.1016/j.jorganchem.2005.12.044

Reference yield: 40.0%

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3) + (S)-glycidyl butyrate (65031-96-1)

Guidance literature:

With (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water; In tetrahydrofuran; at 0 ℃; for 12h; optical yield given as %ee;

DOI:10.2174/157017811795371412

Reference yield:

(+/-)-glycidyl butyrate (2461-40-7) → 1-sn-monobutyroylglycerol (5309-42-2) + (R)-glycidyl butyrate (60456-26-0) + (S)-glycidyl butyrate (65031-96-1)

Guidance literature:

With 4CF₃O₃S^(1-)*Co⁽³⁺⁾*Y⁽³⁺⁾*C₃₆H₅₂N₂O₂^(2-); water; In neat (no solvent); at 20 ℃; for 12h; Overall yield = 19 %; enantioselective reaction;

DOI:10.1039/c5ra12408e

upstream raw materials:

(+/-)-glycidyl butyrate

Downstream raw materials:

(S)-5-(hydroxymethyl)-3-phenyloxazolidin-2-one

(S)-3-(3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

(S)-3-(3-fluoro-4-methyl-phenyl)-5-hydroxymethyl-oxazolidin-2-one

C₁₀H₉F₂NO₃

Refernces

• 1、 Jiang, Chengjun,Yan, Jianbo. "Stereoselective synthesis of (R)-glycidyl butyrate from racemic glycidyl butyrate or epichlorohydrin via hydrolytic kinetic resolution". scheme or table. p. 242 - 243. Retrieved 2012/05/19.