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METHYL 2-METHYLGLYCIDATE, also known as methyl 2-methyloxirane-2-carboxylate, is an ester derived epoxide. It is formed by the reaction of methyl pyruvate with diazomethane and serves as an intermediate in the synthesis of various compounds, including 1,2,4-oxadiazole derivatives.

58653-97-7

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58653-97-7 Usage

Uses

Used in Chemical Synthesis:
METHYL 2-METHYLGLYCIDATE is used as a synthetic intermediate for the production of various compounds, such as 2-methyl-2-hydroxy-1-propanol, 2,3-dihydroxy-2-methyl propionic acid, and methyl 2-hydroxy-3-((4-methoxyphenyl)sulfonyl)-2-methylpropanoate. Its role in these syntheses is crucial for the development of new chemicals with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYL 2-METHYLGLYCIDATE is used as a key component in the synthesis of 1,2,4-oxadiazole derivatives. These derivatives have been studied for their potential applications as pharmaceutical agents, including their use in the development of new drugs for various medical conditions.
Used in Research and Development:
METHYL 2-METHYLGLYCIDATE is also utilized in research and development settings, where it contributes to the advancement of chemical knowledge and the discovery of new compounds with potential applications in various fields, such as materials science, agriculture, and environmental science.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 89, 1955 DOI: 10.1021/ja01606a029

Check Digit Verification of cas no

The CAS Registry Mumber 58653-97-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,6,5 and 3 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 58653-97:
(7*5)+(6*8)+(5*6)+(4*5)+(3*3)+(2*9)+(1*7)=167
167 % 10 = 7
So 58653-97-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O3/c1-5(3-8-5)4(6)7-2/h3H2,1-2H3

58653-97-7 Well-known Company Product Price

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  • Aldrich

  • (423955)  Methyl2-methylglycidate  99%

  • 58653-97-7

  • 423955-1G

  • 831.87CNY

  • Detail
  • Aldrich

  • (423955)  Methyl2-methylglycidate  99%

  • 58653-97-7

  • 423955-5G

  • 3,101.67CNY

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58653-97-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 2-methyloxirane-2-carboxylate

1.2 Other means of identification

Product number -
Other names methyl 2-methyl-oxirane-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58653-97-7 SDS

58653-97-7Relevant articles and documents

Alkylglycidic Acids: Potential New Hypoglycemic Agents

Ho, Winston,Tutwiler, Gene F.,Cottrell, Sandra C.,Morgans, Dave J.,Tarhan, Okan,Mohrbacher, Richard J.

, p. 2184 - 2190 (1986)

A series of alkylglycidic acid analogues and derivatives were synthesized and tested for their ability to inhibit long-chain fatty acid oxidation in vitro and to lower blood sugar in rats.The extent of inhibition of carnitine acyl transferase, the enzyme

SYSTEMS AND METHODS FOR REGIOSELECTIVE CARBONYLATION OF 2,2-DISUBSTITUTED EPOXIDES

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Paragraph 0147; 0165, (2020/06/05)

Provided are methods of carbonylating cyclic substrates to produce carbonyl ated cyclic products. The cyclic substrates may be 2, 2-di substituted epoxides and the cyclic products may be β,β-di substituted lactones. The method may be carried out by forming and pressurizing a reaction mixture of the cyclic substrate, a solvent, carbon monoxide, and a [LA+][CO(CO)4-] catalyst, where [LA+] is a Lewis acid capable of coordinating to the cyclic substrate. The method may proceed with a regioselectivity of 90:10 or greater. The resulting carbonylated cyclic products may be converted to ketone aldol products that retain the stereochemistry and enantiomeric ratio of the carbonyl ated cyclic products.

Regioselective Carbonylation of 2,2-Disubstituted Epoxides: An Alternative Route to Ketone-Based Aldol Products

Hubbell, Aran K.,Lapointe, Anne M.,Lamb, Jessica R.,Coates, Geoffrey W.

supporting information, p. 2474 - 2480 (2019/02/14)

We report the regioselective carbonylation of 2,2-disubstituted epoxides to β,β-disubstituted β-lactones. Mechanistic studies revealed epoxide ring-opening as the turnover limiting step, an insight that facilitated the development of improved reaction conditions using weakly donating, ethereal solvents. A wide range of epoxides can be carbonylated to β-lactones, which are subsequently ring-opened to produce ketone-based aldol adducts, providing an alternative to the Mukaiyama aldol reaction. Enantiopure epoxides were demonstrated to undergo the carbonylation/ring-opening process with retention of stereochemistry to form enantiopure β-hydroxy esters.

1,2,4-Oxadiazoles: A new class of anti-prostate cancer agents

Khatik, Gopal L.,Kaur, Jasmine,Kumar, Varun,Tikoo, Kulbhushan,Nair, Vipin A.

scheme or table, p. 1912 - 1916 (2012/04/04)

Sulfide and sulfonyl derivatives of 1,2,4-oxadiazoles were synthesized and screened by MTT assay on the prostate cancer cells, DU-145. Six compounds were identified as potential anti-prostate cancer agents with IC50 values ranging from 0.5 to 5

Epoxidation and oxidation reactions using divinyl benzene crosslinked polystyrene supported t-butyl hydroperoxide

Sheela,Sreekumar

, p. 943 - 950 (2007/10/03)

Divinyl benzene (DVB) crosslinked polystyrene supported t-butyl hydroperoxide resin has been prepared and employed in the epoxidation of olefins and oxidation of alcohols. The reagent is found to be efficient as the low molecular weight t-butyl hydroperoxide. Presence of catalyst enhanced the reaction efficiency remarkably. Influence of various reaction parameters such as solvent, temperature and molar excess of the reagent on the reactivity of the polymeric reagent is also being investigated.

Catalyst-free gas-phase epoxidation of alkenes

Berndt, Torsten,Boege, Olaf

, p. 584 - 585 (2007/10/03)

Butadiene, styrene, cyclohexene, allyl acetate, methyl methacrylate, and allyl alcohol were epoxidized in a gas-phase reaction in the absence of a catalyst. The applied oxidizing agent is ozone. With exception of allyl alcohol (selectivity to glycidol: 58%), the selectivity to the corresponding epoxide ranged from 88 to 97%. For acrylonitrile, there was no measureable conversion. Copyright

Process for making bicalutamide and intermediates thereof

-

Page 18, (2010/02/06)

Bicalutamide and/or its intermediates are made by the use of p-fluorobenzenesulfinic acid salt as a reagent.

Efficient epoxidation of electron-deficient olefins with a cationic manganese complex

Murphy, Andrew,Dubois, Geraud,Stack

, p. 5250 - 5251 (2007/10/03)

The complex [MnII(R,R-mcp)(CF3SO3)2] is an efficient and practical catalyst for the epoxidation of electron-deficient olefins. This catalyst is capable of epoxidizing olefins with as little as 0.1 mol % catalyst in under 5 min using 1.2 equiv of peracetic acid as the terminal oxidant. A wide scope of substrates are epoxidized including terminal, tertiary, cis and trans internal, enones, and methacrylates with >85% isolated yields. Copyright

Process for making bicalutamide and intermediates thereof

-

, (2008/06/13)

Bicalutamide and/or its intermediates are made by the use of p-fluorobenzenesulfinic acid salt as a reagent.

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