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 
• 16874-33-2 tetrahydro-2-furancarboxylic acid 
• 625-38-7 but-3-enoic acid 
• 3724-55-8 methyl but-3-enoate 
• 201230-82-2 carbon monoxide 
• 111-66-0 oct-1-ene 

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 
• 1171384-62-5 C₁₉H₁₆N₂O₄ 
• 1510835-42-3 1-(benzyloxy)-6-(dimethoxymethyl)-2-piperidinone 
• 154742-64-0 methyl 6-methoxy-5-hexenoate 
• 105373-64-6 methyl (5E)-6-(methylthio)-5-hexenoate 
• 105373-65-7 methyl (5Z)-6-(methylthio)-5-hexenoate 
• 1510835-78-5 1-(O-benzyloxyamino)-6-methoxy-5-hexen-1-one 

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.

METHOD FOR HYDROFORMYLATION

The present invention relates to a process for the hydroformylation of compounds of the formula (I), where X is C, P(Rx), P(O—Rx) S or S(═O), where Rx is H, alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; A is a divalent bridging group having from 1 to 4 bridging atoms; and R1 is H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; or salts thereof; in which the compound of the formula (I) is reacted with carbon monoxide and hydrogen in the presence of a catalyst comprising a complex of a metal of transition group VIII with a compound of the formula (II), where Pn is a pnicogen atom; W is a divalent bridging group having from 1 to 8 bridging atoms; R2 is a functional group capable of forming an intermolecular, noncovalent bond with the group —X(═O)OH; R3, R4 are each alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; a, b, c are each 0 or 1; and Y1, Y2 and Y3 are each O, S, NRa or SiRbRc; and also compounds of the formula (II.a), where W′ is a divalent bridging group having from 1 to 5 bridging atoms between the flanking bonds, Z is O, S, S(═O), S(═O)2, N(RIX) or C(RIX)(RX); and RI to RX are each, independently of one another, H, halogen, nitro, cyano, amino, alkyl, etc.; or two radicals RI, RII, RIV, RVI, RVIII and RIX together represent the second part of a double bond.

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.