(R)-Dimethyl 2-hydroxysuccinate

Base Information

• Chemical Name: (R)-Dimethyl 2-hydroxysuccinate
• CAS No.: 70681-41-3
• Molecular Formula: C6H10O5
• Molecular Weight: 162.142
• Hs Code.: 29181990
• European Community (EC) Number: 829-455-0
• DSSTox Substance ID: DTXSID30892495
• Nikkaji Number: J231.848B
• Wikidata: Q72470822
• Mol file: 70681-41-3.mol

Synonyms:70681-41-3;(R)-Dimethyl 2-hydroxysuccinate;D-(+)-Malic Acid Dimethyl Ester;dimethyl (2R)-2-hydroxybutanedioate;Dimethyl (R)-(+)-malate;Butanedioic acid, hydroxy-, dimethyl ester, (2R)-;1,4-Dimethyl (2R)-2-Hydroxybutanedioate;Dimethyl D-malate;dimethyl (r)-malate;(+)-Dimethyl malate;Dimethyl D-(+)-Malate;D-Malic Acid Dimethyl Ester;SCHEMBL1691025;DTXSID30892495;YSEKNCXYRGKTBJ-SCSAIBSYSA-N;D-(+)-Apple Acid Dimethyl Ester;Dimethyl (R)-2-hydroxybutanedioate;Dimethyl (R)-(+)-malate, 98%;MFCD00066216;AKOS015910996;CS-W016123;(R)-2-hydroxysuccinic acid dimethylester;AS-60590;(R)-2-hydroxysuccinic acid dimethyl ester;M1347;D91488;EN300-183703;A866566

Chemical Property of (R)-Dimethyl 2-hydroxysuccinate

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: n20/D 1.440
• Boiling Point: 249.6 °C at 760 mmHg
• PKA: 11.72±0.20(Predicted)
• Flash Point: 100 °C
• PSA: 72.83000
• Density: 1.224 g/cm³
• LogP: -0.91660
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl D-(+)-Malate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(C(=O)OC)O
• Isomeric SMILES: COC(=O)C[C@H](C(=O)OC)O

Technology Process of (R)-Dimethyl 2-hydroxysuccinate

There total 36 articles about (R)-Dimethyl 2-hydroxysuccinate 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: 100.0%

methanol (67-56-1) + D-Malic acid (636-61-3,78644-42-5) → (R)-dimethyl malate (70681-41-3)

Guidance literature:

With thionyl chloride;

DOI:10.1016/S0968-0896(02)00023-8

Reference yield: 99.0%

(2R,3S)-dimethyl oxirane-2,3-dicarboxylate (56958-97-5,718617-86-8) → (R)-dimethyl malate (70681-41-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; Ambient temperature;

Reference yield: 98.0%

(R)-2-(tert-Butyl-dimethyl-silanyloxy)-succinic acid dimethyl ester → (R)-dimethyl malate (70681-41-3)

Guidance literature:

With cerium(III) chloride; sodium iodide; In acetonitrile; for 10h; Heating;

DOI:10.1055/s-1998-1601

upstream raw materials:

methanol

D-Malic acid

diazomethane

malic acid

Downstream raw materials:

(R)-2-Acetoxy-bernsteinsaeuredimethylester

Dimethyl (R)-2-(Benzyloxy)succinate

dimethyl (2R)-2-({(2E)-3-[3,4-bis(acetyloxy)phenyl]prop-2-enoyl}oxy)butanedioate

(R)-2-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

Refernces

• 1、 Alpegiani, Marco,Hanessian, Stephen. "A Facile Access to (R)-Malic Acid". . p. 278 - 279. Retrieved 1987.
• 2、 Tinto,Simmons-Boyce,McLean,Reynolds. "Constituents of Agave americana and Agave barbadensis". . p. 594 - 597. Retrieved 2005.
• 3、 -. "USE OF PHENOLIC COMPOUNDS FROM OLEA EUROPAEA". Page/Page column 48-49. . Retrieved 2019/02/25.
• 4、 Striegler, Susanne,Fan, Qiu-Hua,Rath, Nigam P.. "Binuclear copper(II) complexes discriminating epimeric glycosides and α- And β-glycosidic bonds in aqueous solution". . p. 349 - 364. Retrieved 2016/05/24.