Ethyl 2-(hydroxyimino)-3-oxobutanoate

Base Information

• Chemical Name: Ethyl 2-(hydroxyimino)-3-oxobutanoate
• CAS No.: 5408-04-8
• Molecular Formula: C6H9NO4
• Molecular Weight: 159.142
• Hs Code.: 2928000090
• Mol file: 5408-04-8.mol

Synonyms:Butanoic acid, 2-(hydroximino)-3-oxo-, ethyl ester;AC1O4QVU;SBB049552;STK505578;

Chemical Property of Ethyl 2-(hydroxyimino)-3-oxobutanoate

Chemical Property:

• Vapor Pressure: 0.00121mmHg at 25°C
• Melting Point: 46-48°C
• Refractive Index: 1.476
• Boiling Point: 266.1 °C at 760 mmHg
• PKA: 7.41±0.10(Predicted)
• Flash Point: 114.7 °C
• PSA: 75.96000
• Density: 1.22 g/cm³
• LogP: -0.03130
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

Ethyl-2-(hydroxyimino)-3-oxobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl-2-(hydroxyimino)-3-oxobutanoate (cas# 5408-04-8) is a compound useful in organic synthesis.

Technology Process of Ethyl 2-(hydroxyimino)-3-oxobutanoate

There total 20 articles about Ethyl 2-(hydroxyimino)-3-oxobutanoate 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: 99.0%

ethyl acetoacetate (141-97-9) → ethyl 2-hydroxyimino-3-oxobutanoate (5408-04-8)

Guidance literature:

ethyl acetoacetate; With acetic acid; sodium nitrite; In water; at 0 ℃;

With sodium hydrogencarbonate; In water; pH=7 - 8;

Reference yield:

ethyl acetoacetate (141-97-9) → ethyl 2,2-dichloroacetoacetate (6134-66-3) + ethyl 2-chloro-3-oxo-butyrate (609-15-4) + ethyl 2-hydroxyimino-3-oxobutanoate (5408-04-8)

Guidance literature:

With Nitryl chloride; In dichloromethane; at 20 ℃; for 2h; Product distribution; variation of molar ratio of NO₂Cl/educt, solvent, temperature and add. of CaCl₂ or Na₂SO₄;

DOI:10.1007/BF00903330

Reference yield:

→ 3-acetyl-4,5-dimethyl-pyrrole-2-carboxylic acid (2386-33-6) + ethyl 2-hydroxyimino-3-oxobutanoate (5408-04-8)

Guidance literature:

upstream raw materials:

ethyl 3-ethoxy-2-butenoate

diethyl acetylmalonate

methyl nitrite

sodium ethanolate

Downstream raw materials:

ethyl 3-methyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

NSC 15758

diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate

ethyl 4-(phenylcarbamoyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate

Refernces

• 1、 Egorov,Gimalova. "Synthesis of a Precursor of the Antiviral Agent A-315675". . p. 241 - 244. Retrieved 2019.
• 2、 Harvey et al.. "". . p. 529. Retrieved 1978.
• 3、 Hickey, James L.,James, Janine L.,Henderson, Clare A.,Price, Katherine A.,Mot, Alexandra I.,Buncic, Gojko,Crouch, Peter J.,White, Jonathan M.,White, Anthony R.,Smith, Trevor A.,Donnelly, Paul S.. "Intracellular Distribution of Fluorescent Copper and Zinc Bis(thiosemicarbazonato) Complexes Measured with Fluorescence Lifetime Spectroscopy". . p. 9556 - 9567. Retrieved 2015.
• 4、 Juillet, Charlotte,Ermolenko, Ludmila,Boyarskaya, Dina,Baratte, Blandine,Josselin, Béatrice,Nedev, Hristo,Bach, Stéphane,Iorga, Bogdan I.,Bignon, Jér?me,Ruchaud, Sandrine,Al-Mourabit, Ali. "From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase". . p. 1197 - 1219. Retrieved 2021/02/05.
• 5、 Kokkonda, Sreekanth,Deng, Xiaoyi,White, Karen L.,El Mazouni, Farah,White, John,Shackleford, David M.,Katneni, Kasiram,Chiu, Francis C. K.,Barker, Helena,Mclaren, Jenna,Crighton, Elly,Chen, Gong,Angulo-Barturen, Inigo,Jimenez-Diaz, Maria Belen,Ferrer, Santiago,Huertas-Valentin, Leticia,Martinez-Martinez, Maria Santos,Lafuente-Monasterio, Maria Jose,Chittimalla, Rajesh,Shahi, Shatrughan P.,Wittlin, Sergio,Waterson, David,Burrows, Jeremy N.,Matthews, Dave,Tomchick, Diana,Rathod, Pradipsinh K.,Palmer, Michael J.,Charman, Susan A.,Phillips, Margaret A.. "Lead optimization of a pyrrole-based dihydroorotate dehydrogenase inhibitor series for the treatment of malaria". . p. 4929 - 4956. Retrieved 2020/06/08.