Diethyl 2-hydroxypentanedioate

Base Information

• Chemical Name: Diethyl 2-hydroxypentanedioate
• CAS No.: 69134-53-8
• Molecular Formula: C9H16O5
• Molecular Weight: 204.22
• DSSTox Substance ID: DTXSID90533579
• Wikidata: Q27159500
• Mol file: 69134-53-8.mol

Synonyms:diethyl 2-hydroxypentanedioate;69134-53-8;Diethyl 2-hydroxyglutarate;2-hydroxyglutaric acid diethyl ester;Diethyl2-hydroxyglutarate;diethyl2-hydroxypentanedioate;SCHEMBL8100254;CHEBI:87295;DTXSID90533579;DYLHSDCNOUDICA-UHFFFAOYSA-N;MFCD16620610;AKOS015843401;CS-W007118;DS-9352;Diethyl 2-Hydroxypentanedioate (>90%);A9160;Pentanedioic acid, 2-hydroxy-1,5-diethyl ester;Pentanedioic acid,2-hydroxy-,1,5-diethyl ester;Q27159500;Diethyl2-hydroxyglutarate,2-Hydroxyglutaricaciddiethylester;PENTANEDIOIC ACID, 2-HYDROXY-, 1,5-DIETHYL ESTER

Chemical Property of Diethyl 2-hydroxypentanedioate

Chemical Property:

• Vapor Pressure: 0.000205mmHg at 25°C
• Refractive Index: 1.448
• Boiling Point: 291.8°C at 760 mmHg
• PKA: 12.84±0.20(Predicted)
• Flash Point: 107.8°C
• PSA: 72.83000
• Density: 1.122g/cm³
• LogP: 0.25370
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 204.09977361
• Heavy Atom Count: 14
• Complexity: 190

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl2-Hydroxypentanedioate(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCC(C(=O)OCC)O

Technology Process of Diethyl 2-hydroxypentanedioate

There total 13 articles about Diethyl 2-hydroxypentanedioate 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: 82.0%

(E)-diethyl glutaconate (73178-43-5) → (+/-)-diethyl 2-hydroxypentandioate (69134-53-8)

Guidance literature:

With phenylsilane; oxygen; bis(dipivaloylmethanato)manganese(II); In ethanol; at 0 ℃; for 4h; under 760 Torr;

DOI:10.1246/cl.1990.1869

Reference yield: 74.0%

diethyl 2-ketoglutarate (5965-53-7) → (+/-)-diethyl 2-hydroxypentandioate (69134-53-8)

Guidance literature:

With sodium tetrahydroborate;

DOI:10.1016/S0957-4166(99)00286-4

Reference yield:

→ (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester (1126-51-8) + (+/-)-diethyl 2-hydroxypentandioate (69134-53-8)

Guidance literature:

With ethanol; sulfuric acid;

upstream raw materials:

2-hydroxyglutaric acid

diethyl 2-ketoglutarate

(E)-diethyl glutaconate

ethanol

Downstream raw materials:

(+/-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester

(R)-(-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester

(S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester

Refernces

• 1、 Balazsik, Katalin,Szoeri, Kornel,Felfoeldi, Karoly,Toeroek, Bela,Bartok, Mihaly. "Asymmetric synthesis of alkyl 5-oxotetrahydrofuran-2-carboxylates by enantioselective hydrogenation of dialkyl 2-oxoglutarates over cinchona modified Pt/Al2O3 catalysts". . p. 555 - 556. Retrieved 2007/10/03.
• 2、 Drioli, Sara,Nitti, Patrizia,Pitacco, Giuliana,Tossut, Laura,Valentin, Ennio. "Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates". . p. 2713 - 2728. Retrieved 2007/10/03.