ETHYL (S)-3,4-EPOXYBUTANOATE

Base Information

• Chemical Name: ETHYL (S)-3,4-EPOXYBUTANOATE
• CAS No.: 112083-63-3
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID00448281
• Nikkaji Number: J1.032.473D
• Wikidata: Q27461593
• Mol file: 112083-63-3.mol

Synonyms:(S)-Ethyl 2-(oxiran-2-yl)acetate;Oxiraneacetic acid, ethyl ester, (S)-;Oxiraneaceticacid, ethyl ester, (2S)- (9CI);

Chemical Property of ETHYL (S)-3,4-EPOXYBUTANOATE

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 2.65mmHg at 25°C
• Refractive Index: 1.44
• Boiling Point: 158.257 °C at 760 mmHg
• Flash Point: 73.463 °C
• PSA: 38.83000
• Density: 1.1 g/cm³
• LogP: 0.33840
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Decomposes in water.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 111

Purity/Quality:

99% ^*data from raw suppliers

Ethyl (S)-3,4-epoxybutanoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1CO1
• Isomeric SMILES: CCOC(=O)C[C@H]1CO1
• Uses: Mainly employed inorganic synthesis. They are starting materials for the condensation reactions. Homoallylic alcohol is readily available from the regiospecific ring opening of commercially available ethyl (S)-oxiranyl acetate with the cuprate derived from vinylmagnesium bromide and copper bromide-dimethyl sulfide complex in 88 % yield.

Technology Process of ETHYL (S)-3,4-EPOXYBUTANOATE

There total 6 articles about ETHYL (S)-3,4-EPOXYBUTANOATE 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: 94.0%

(S)-4-iodo-3-hydroxy-butyric acid ethyl ester (112100-39-7,159614-88-7) → ethyl (-)-(2S)-oxirane-2-acetate (112083-63-3)

Guidance literature:

With silver(l) oxide; In acetonitrile; Ambient temperature;

DOI:10.1016/S0957-4166(98)00441-8

Reference yield: 55.0%

ethyl (S)-3-((tert-butyldimethylsilyl)oxy)-4-iodobutanoate (130158-22-4) → ethyl (-)-(2S)-oxirane-2-acetate (112083-63-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)86765-X

Reference yield: 44.0%

(+/-)-ethyl-3,4-epoxybutanoate (32223-97-5) → ethyl (-)-(2S)-oxirane-2-acetate (112083-63-3) + (+)-(R)-ethyl 3,4-dihydroxybutanoate (112635-76-4) + (S)-ethyl 3,4-dihydroxybutanoate (112635-76-4,108585-47-3)

Guidance literature:

With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ja016737l

upstream raw materials:

ethyl (S)-3-((tert-butyldimethylsilyl)oxy)-4-iodobutanoate

(S)-4-iodo-3-hydroxy-butyric acid ethyl ester

(+/-)-ethyl-3,4-epoxybutanoate

ethyl (S)-4-chloro-3-hydroxybutanoate

Downstream raw materials:

ethyl (R)-3-hydroxyhexanoate

(R)-ethyl 4-cyano-3-hydroxybutyrate

(R)-(-)-Ethyl 3-hydroxy-4-phenylbutanoate

(R)-3-hydroxytetradecanoic acid ethyl ester

Refernces

• 1、 Huang, Guangfei,Hollingsworth, Rawle I.. "An efficient synthesis of (R)-3-hydroxytetradecanoic acid". . p. 4113 - 4115. Retrieved 1998.
• 2、 Sunnapu, Ranganayakulu,Rajendar, Goreti. "A Concise Stereoselective Total Synthesis of Methoxyl Citreochlorols and Their Structural Revisions". . p. 1637 - 1642. Retrieved 2021/03/15.
• 3、 -. "SYNTHETIC DERIVATIVES OF MPL AND USES THEREOF". Paragraph 0146. . Retrieved 2014/11/13.