Ethyl glyoxalate

Base Information

• Chemical Name: Ethyl glyoxalate
• CAS No.: 924-44-7
• Molecular Formula: C4H6O3
• Molecular Weight: 102.09
• Hs Code.: 29183000
• European Community (EC) Number: 213-105-3
• NSC Number: 49206
• UNII: IXX9MQ1J1I
• DSSTox Substance ID: DTXSID6061282
• Nikkaji Number: J298.483K
• Wikidata: Q27124039
• Metabolomics Workbench ID: 58605
• Mol file: 924-44-7.mol

Synonyms:Aceticacid, oxo-, ethyl ester (9CI);Glyoxylic acid, ethyl ester (6CI,7CI,8CI);Ethyl 2-oxoacetate;Ethyl oxoacetate;NSC 49206;Oxoacetic acidethyl ester;

Chemical Property of Ethyl glyoxalate

Chemical Property:

• Appearance/Colour: Clear colorless to slightly yellow solution
• Vapor Pressure: 11.7mmHg at 25°C
• Refractive Index: 1.4750
• Boiling Point: 126.4 °C at 760 mmHg
• Flash Point: 41.7 °C
• PSA: 43.37000
• Density: 1.07 g/cm³
• LogP: -0.25160
• Storage Temp.: Refrigerator
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Immiscible with water.
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 102.031694049
• Heavy Atom Count: 7
• Complexity: 77

Purity/Quality:

99.9% ^*data from raw suppliers

EthylGlyoxylate(>50%inToluene) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-38-43-48/20-63-65-67
• Safety Statements: 36/37-62-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C=O
• Uses: Ethyl glyoxylate is widely used as an intermediate in the synthesis of pharmaceuticals (high reactivity of aldehyde function). It is used in the synthesis of a biodegradable polymer, poly(ethyl glyoxylate). It is actively involved in the Friedel-Crafts alkylation reactions with thiophenes to give the corresponding secondary alcohols.

Technology Process of Ethyl glyoxalate

There total 69 articles about Ethyl glyoxalate 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%

diethyl (2S,3S)-tartrate (13811-71-7) → glyoxylic acid ethyl ester (924-44-7)

Guidance literature:

With periodic acid; In diethyl ether; water; for 1h; Inert atmosphere;

DOI:10.1039/c4ra04845h

Reference yield: 53.0%

ethyl acrylate (140-88-5,9003-32-1) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + glyoxylic acid ethyl ester (924-44-7)

Guidance literature:

With ozone; at 20.84 ℃; under 760 Torr; Kinetics; Darkness;

DOI:10.1021/jp104451v

Reference yield: 30.0%

ethyl 3-ethoxypropionate (763-69-9) → glyoxylic acid ethyl ester (924-44-7) + 3-oxo-propionic acid ethyl ester (34780-29-5) + acetaldehyde (75-07-0,9002-91-9) + 3-Formyloxy-propionic acid ethyl ester + formic acid ethyl ester (109-94-4)

Guidance literature:

With dodecane; methyl nitrite; nitrogen(II) oxide; at 23.9 ℃; under 760 Torr; Rate constant; Product distribution; Mechanism; Irradiation;

DOI:10.1002/(sici)1097-4601(1997)29:8<637::aid-kin9>3.0.co;2-v

upstream raw materials:

Diethyl tartrate

(+/-)-diethyl tartrate

ethyl 2-hydroxyacetate

ethyl acetoacetate

Downstream raw materials:

ethyl 2-ethoxyglycolate

ethyl 2-(2-carbamoylhydrazono)acetate

phenylhydrazone of ethyl ester of glyoxalic acid

ethyl 2-(hydroxyimino)acetate

Refernces

• 1、 Watanabe, Kenji,Terao, Nodoka,Kii, Isao,Nakagawa, Reiko,Niwa, Takashi,Hosoya, Takamitsu. "Indolizines Enabling Rapid Uncaging of Alcohols and Carboxylic Acids by Red Light-Induced Photooxidation". supporting information. p. 5434 - 5438. Retrieved 2020/07/24.
• 2、 Smits,Audic,Wodrich,Corminboeuf,Cramer. "A β-Carbon elimination strategy for convenient: In situ access to cyclopentadienyl metal complexes". . p. 7174 - 7179. Retrieved 2017/10/05.