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2-Oxo-2-oxonioacetate

Base Information Edit
  • Chemical Name:2-Oxo-2-oxonioacetate
  • CAS No.:144-62-7
  • Molecular Formula:C2H2O4
  • Molecular Weight:90.0355
  • Hs Code.:2917111000
  • Mol file:144-62-7.mol
2-Oxo-2-oxonioacetate

Synonyms:hydron;oxalate;2-oxo-2-oxonioacetate

Suppliers and Price of 2-Oxo-2-oxonioacetate
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
Total 639 raw suppliers
Chemical Property of 2-Oxo-2-oxonioacetate Edit
Chemical Property:
  • Appearance/Colour:Odorless white solid 
  • Vapor Pressure:2.51E-06mmHg at 25°C 
  • Melting Point:189-191 °C 
  • Boiling Point:365.099 °C at 760 mmHg 
  • PKA:1.38±0.54(Predicted) 
  • Flash Point:188.79 °C 
  • PSA:74.60000 
  • Density:1.772 g/cm3 
  • LogP:-0.84440 
  • Water Solubility.:90 g/L (20℃) 
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:4
  • Rotatable Bond Count:0
  • Exact Mass:89.99530854
  • Heavy Atom Count:6
  • Complexity:60.5
Purity/Quality:

99% *data from raw suppliers

Safty Information:
  • Pictogram(s): HarmfulXn 
  • Hazard Codes: Xn:Harmful;
     
  • Statements: R21/22:; 
  • Safety Statements: S24/25:; 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Canonical SMILES:[H+].[H+].C(=O)(C(=O)[O-])[O-]
  • Chemical Properties Oxalic acid, an alpha,omega-dicarboxylic acid, is the simplest of the dicarboxylic acids and has been known since its discovery by Scheele in 1734. It serves as a potential sustainable platform chemical with applications in various industries.
  • Uses The pharmaceutical industry is the largest consumer of oxalic acid, but it also finds use in agriculture, textiles, and leather industries. In the pharmaceutical sector, oxalic acid serves various purposes. Additionally, it is utilized as an acid rinse in laundries for removing rust and ink stains. Oxalic acid's leaching properties make it valuable in solubilizing heavy metals in materials like bauxite, clay, sewage sludge, and electronic waste. Its natural presence in many vegetable food products allows for its use as a natural anti-browning and preservation agent in fruit and vegetable storage.
  • Role in Organic Chemistry Oxalic acid serves as a precursor for glyoxylic acid, an important C2 building block for various organic molecules used in industries such as agrochemicals, aromas, cosmetic ingredients, pharmaceutical intermediates, and polymers.
  • Biological Interactions and Environmental Impact Oxalic acid plays a significant role in activating the uptake of perfluorooctanoic acid (PFOA) in soils, particularly through root exudates. It inhibits PFOA sorption to soils and enhances the dissolution of metallic ions and organic matter from soils, forming oxalate-metal complexes. These findings shed light on the mechanisms of PFOA activation in soils and provide insights into enhancing PFOA accumulation in lettuce varieties through oxalic acid at rhizospheric concentrations.
  • Production Methods The oldest route for oxalic acid production, discovered by Bergmann in 1776, involves the oxidation of biomass, particularly carbohydrates, using nitric acid. However, concerns about competition with food production and reliance on fossil fuels have prompted exploration into alternative production methods. Currently, oxalic acid is predominantly produced from fossil naphtha via propylene and ethylene glycol or CO obtained from coal.
  • General Description Oxalic acid is a versatile and eco-friendly catalyst used in organic synthesis, particularly for converting dithioacetals to carbonyl compounds, offering a green alternative to toxic heavy metal salts. It also facilitates the mild, racemization-free cleavage of ketone SAMP-hydrazones, enabling high-yield recovery of chiral auxiliaries without compromising enantiomeric purity. Additionally, oxalic acid derivatives serve as key ligands in the synthesis of dimetallic complexes, contributing to advancements in catalysis and magnetic materials. Its applications highlight its role as a sustainable and efficient reagent in diverse chemical processes.
Technology Process of 2-Oxo-2-oxonioacetate

There total 2193 articles about 2-Oxo-2-oxonioacetate 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:
Guidance literature:
With osmium(VIII) oxide; dihydrogen peroxide; tert-butyl alcohol; at 0 ℃;
DOI:10.1021/ja01298a065
Refernces Edit

Oxalic acid catalyzed reaction between dithioacetals and acetals. A simple and eco-friendly method for a conversion of a dithioacetal to a carbonyl compound

10.1016/j.tetlet.2006.06.131

The study presents an eco-friendly and cost-effective method for converting dithioacetals to carbonyl compounds using oxalic acid as a catalyst. Dithioacetals, which are stable functional groups used as acyl anion equivalents and protecting groups in organic synthesis, are typically challenging to convert into carbonyl compounds due to their stability. Traditional methods often involve toxic heavy metal salts like HgCl2, which pose environmental and disposal challenges. In this research, oxalic acid catalyzes the hydrolysis of dithioacetals in the presence of acetals such as dimethoxymethane (DMM) or diethoxymethane (DEM), yielding carbonyl compounds and bis(dodecylthio)methane. The reaction is effective for both aldehydes and ketones, with nitromethane as the preferred solvent. The study highlights the use of oxalic acid as a green alternative to toxic reagents, offering high yields and recyclability of dithioacetals. The proposed mechanism involves protonation of the acetal, nucleophilic attacks by sulfur atoms, and subsequent eliminations leading to the formation of carbonyl compounds.

Practical syntheses of the adhesion molecule inhibitor ER-49890 and its stereoisomer

10.3987/COM-04-10279

The research focuses on the practical syntheses of the adhesion molecule inhibitor ER-49890 and its stereoisomer. The study reports improved synthetic routes for both the anti- and syn-isomers, with a key innovation being the stereoselective synthesis of the anti-(3-azabicyclo[3.3.1]non-9-yl)acetic acid side chain (anti-12) using Pd/C hydrogenation in the presence of HCl. The syn-isomer (syn-12) was obtained through a crystallization process as its oxalic acid salt from a mixture of anti- and syn-isomers. The 10H-pyrazino[2,3-b][1,4]benzothiazine core (7) was prepared from commercially available 4-chloro-3-nitrobenzyl alcohol (13) in a four-step process with good yield. The experiments involved various reactants, including sodium sulfide, 2,3-dichloropyrazine, triphenylphosphine, and iron powder, among others, and employed techniques such as HPLC, IR spectroscopy, NMR spectroscopy, and mass spectrometry for analysis. The study also detailed the effects of different solvents and additives on the hydrogenation process, leading to a selective synthesis of anti-12 with improved yields.

Synthesis and properties of dimetallic complexes based on a new oxalamidine-derived ligand system with pendant pyridine functionality

10.1002/1099-0682(200103)2001:3<805::AID-EJIC805>3.0.CO;2-2

The study focuses on the synthesis and properties of dimetallic complexes based on a new oxalamidine-derived ligand system with pendant pyridine functionality. The researchers used sterically hindered bis(imidoyl)chlorides of oxalic acid and picolylamine to create conformationally locked oxalic acid-derived amidines with pendant pyridine functional groups. These amidines served as multivalent ligands for the formation of heterodimetallic and homodimetallic diazadiene complexes, which are of interest due to their potential cooperative effects in catalysis, intramolecular electron transfer reactions, and magnetic interactions. The study also explores the coordination chemistry of these ligands with various metals, including molybdenum, cobalt, and copper, to understand their conformational restrictions and the role of intramolecular hydrogen bonding in their structure and reactivity. The synthesized complexes were characterized using various analytical techniques, including NMR, IR, and X-ray crystallography.

Mild, racemization free cleavage of ketone SAMP-hydrazones with oxalic acid - Recycling of the chiral auxiliary

10.1055/s-1998-1765

The research focuses on the development of a mild, racemization-free method for cleaving ketone SAMP-hydrazones using oxalic acid. The purpose of this study was to achieve high efficiency in asymmetric synthesis by developing a non-stoichiometric method that allows for the recycling of chiral reagents, specifically the chiral auxiliary SAMP. The researchers concluded that the use of a saturated aqueous solution of oxalic acid for the cleavage of ketone SAMP-hydrazones resulted in the corresponding ketones with excellent yields and high enantiomeric purity (90 - 99%). The chiral auxiliary SAMP could be recovered from the aqueous phase with good yield (85%) and unchanged enantiomeric purity. This method is compatible with functionalities sensitive to oxidative cleavage conditions or strong acids, and it avoids the formation of carcinogenic nitrosoamine by-products, which occur in ozonolysis, and eliminates the need for toxic methylating reagents used in the salt method. The chemicals used in the process include oxalic acid, ketone SAMP-hydrazones, and various ketones as substrates for the cleavage reaction.

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