5746-02-1

Basic information

• Product Name: 5-Oxopentanoic acid
• Synonyms: 4-Formylbutyric acid;5-Oxopentanoic acid;5-Oxovaleric acid;Glutaraldehydic acid;Glutaric semialdehyde
• CAS NO: 5746-02-1
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.1152
• Mol File: 5746-02-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 81-82 °C
• Boiling Point: 273 °C at 760 mmHg
• Flash Point: 133.2 °C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 0.00163mmHg at 25°C
• Refractive Index: 1.436
• PKA: 4.65±0.10(Predicted)
• CAS DataBase Reference: 5-Oxopentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Oxopentanoic acid(5746-02-1)
• EPA Substance Registry System: 5-Oxopentanoic acid(5746-02-1)

Safety Data

• Hazardous Substances Data: 5746-02-1(Hazardous Substances Data)

Usage

General Description

5-Oxopentanoic acid, also known as 5-oxovaleric acid, is a organic compound with the chemical formula C5H8O3. It is a colorless liquid that is used as a precursor in the synthesis of pharmaceuticals and other organic compounds. 5-oxopentanoic acid is a keto acid, meaning it contains a carbonyl group adjacent to a carboxylic acid group. It is also a key intermediate in the biosynthesis of lysine, an essential amino acid. Additionally, 5-oxopentanoic acid has potential applications in the production of flavors and fragrances due to its fruity odor and taste. Overall, this chemical compound has a variety of industrial and biological uses.

InChI:InChI=1/C5H8O3/c6-4-2-1-3-5(7)8/h4H,1-3H2,(H,7,8)

Upstream product

• 120-92-3 cyclopentanone 
• 67-56-1 methanol 
• 10316-66-2 2-hydroxy-2-cyclohexen-1-one 
• 64-17-5 ethanol 
• 111-30-8 Glutaraldehyde 
• 625-38-7 but-3-enoic acid 
• 111-66-0 oct-1-ene 
• 201230-82-2 carbon monoxide 
• 3724-55-8 methyl but-3-enoate 
• 16874-33-2 tetrahydro-2-furancarboxylic acid 

Downstream Products

• 110-94-1 1,5-pentanedioic acid 
• 1065330-02-0 N-[(2,4-dichlorophenyl)methyl]-1-methyl-6-oxo-2-piperidinecarboxamide 
• 1065330-01-9 N-[(2,4-dichlorophenyl)methyl]-1-ethyl-6-oxo-2-piperidinecarboxamide 
• 1510835-78-5 1-(O-benzyloxyamino)-6-methoxy-5-hexen-1-one 
• 105373-64-6 methyl (5E)-6-(methylthio)-5-hexenoate 
• 105373-65-7 methyl (5Z)-6-(methylthio)-5-hexenoate 
• 1510835-42-3 1-(benzyloxy)-6-(dimethoxymethyl)-2-piperidinone 
• 154742-64-0 methyl 6-methoxy-5-hexenoate 
• 1171384-62-5 C₁₉H₁₆N₂O₄ 

Relevant articles and documents

Hydrogenolysis of tetrahydrofuran-2-carboxylic acid over tungsten-modified rhodium catalyst

Catalysts for reduction of tetrahydrofuran-2-carboxylic acid (THFCA), which can be synthesized from furfural via oxidation and hydrogenation, were explored among the combinations of noble metal and reducible metal oxide supported on SiO2. Rh-WOx/SiO2 catalysts showed activity in C-O hydrogenolysis at 2-position of THFCA (to δ-valerolactone and 5-hydroxyvaleric acid) and higher yield ratio of these C-O hydrogenolysis products to carboxylic acid hydrogenation products than other bimetallic catalysts. The activity of Rh-WOx/SiO2 catalysts was highest at W/Rh = 0.25 mol/mol. XRD, TPR, CO adsorption and XAFS characterizations showed that the Rh-WOx/SiO2 (W/Rh = 0.25) catalyst contained Rh metal particles with surface modification with isolated W2+ oxide species. The mechanism that hydride-like species formed on Rh atom attacks the C atom at the α-position (2-position) of adsorbed carboxylate on W atom is proposed based on the similar kinetics and similar catalyst structure to Rh-MOx/SiO2 (M = Re, Mo) which is known to be active in THFA hydrogenolysis to 1,5-pentanediol.

Alternative selective oxidation pathways for aldehyde oxidation and alkene epoxidation on a SiO2-supported Ru-monomer complex catalyst

We have prepared a novel Ru-mononer complex supported on a SiO2 surface by using a Rumonomer complex precursor with a p-cymene ligand, which was found to be highly active for the selective oxidation of aldehydes and the epoxidation of alkenes using O2. The structure of the supported Ru catalyst was characterized by means of FT-IR, solid-state NMR, diffuse-reflectance UV/vis, XPS, Ru K-edge EXAFS, and DFT calculations, which demonstrated the formation of isolatedly located, unsaturated Ru centers behind a p-cymene ligand of the Ru-complex precursor. The site-isolated Ru-monomer complex on SiO2 achieved tremendous TONs (turnover numbers) for the selective oxidation of aldehydes and alkenes; e.g. TONs of 38,800,000 for selective isobutyraldehyde (IBA) oxidation and 2,100,000 for trans-stilbene epoxidation at ambient temperature, which are among the highest TONs in metal-complex catalyzes to our knowledge. We also found that the IBA sole oxidation with an activation energy of 48 kJ mol-1 much more facile than the trans-stilbene epoxidation with an activation energy of 99 kJ mol -1 was completely suppressed by the coexistence of trans-stilbene. The switchover of the selective oxidation pathways from the IBA oxidation to the trans-stilbene epoxidation was explained in terms of energy profiles for the alternative selective oxidation pathways, resulting in the preferential coordination of trans-stilbene to the Ru-complex at the surface. This aspect gives an insight into the origin of the efficient catalysis for selective epoxidation of alkenes with IBA/O2.

Process for intermediates to 1-carbapenems and 1-carbacephems

A stereoselective process for chiral intermediates to 1-carbapenum and 1-carbacephalosporins is provided comprising the use of an N-acyl-(4R)-substituted-1,3-thiazolidine-2-thione as a chiral auxiliary in boron enolate mediated aldol condensation with a protected-β-keto ester aldehyde. E.g., benzyl 3,3-(ethylenedioxy)-4-formylbutyrate is condensed with the boron enolate formed with n-butyryl (4R)-methoxycarbonyl-1,3-thiazolidine-2-thione to provide benzyl 3,3-ethylenedioxy-(5R)-hydroxy-6-[(4R)-methoxycarbonyl-1,3-thiazolidine-2-thione-3-ylcarbonyl]octanoate. Displacement of the thiazolidine-2-thione chiral auxiliary moiety with an O-alkyl, O-acyl or O-aralkyl hydroxyamine provides the corresponding chiral intermediate as the hydroxamate.