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
• General Description: Ethyl glyoxalate is a versatile reagent used in enantioselective reactions, such as the Mukaiyama aldol reaction, to construct key intermediates like γ-butyrolactones, as well as in domino reactions to synthesize complex chiral tricarboxylates with multiple stereocenters. Its reactivity under catalytic conditions enables high enantioselectivity and diastereoselectivity, making it valuable in synthetic organic chemistry for constructing structurally diverse and biologically relevant molecules.

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

An enantioselective Mukaiyama aldol reaction as the key step towards the tetrahydropyran core of psymberin via a γ-butyrolactone intermediate

10.1055/s-0031-1290379

The research focuses on an alternative synthetic route towards the tetrahydropyran core of psymberin, a marine cytotoxin with high cytotoxicity against various cancer cell lines. The key steps involve a catalytic enantioselective Mukaiyama aldol reaction and a syn reduction, which rapidly assemble a γ-lactone precursor for the central fragment of the natural product. The reactants used include silyl enol ether 3 and ethyl glyoxalate (4), with titanium(IV)/6,6′-dibromobinaphthol catalyst D system employed for the aldol reaction. The experiments utilized various catalytic systems and conditions to optimize enantioselectivity and yield, with analyses conducted through techniques such as HPLC, NMR, and IR spectroscopy to confirm the structure and purity of the synthesized compounds.

A domino reaction of a β-ketoester, phenylethylamine and ethyl glyoxylate: leading to chiral tricarboxylate containing multiple stereocenters

10.1016/j.tetasy.2008.10.028

The research focuses on the synthesis of a novel chiral tricarboxylate containing multiple stereocenters through a one-pot domino reaction involving a b-ketoester, (S)-phenylethylamine, and ethyl glyoxylate. The purpose of this study was to develop an efficient method for accessing complex molecules with multiple stereocenters, which is a significant challenge in both academic research and industrial applications. The researchers successfully achieved high yields and diastereoselectivities (up to 96:4 dr) under optimal conditions, and the reaction with Zn(BH4)2 yielded chiral c-lactones with good yields and up to 92:8 dr.