21169-71-1

Basic information

• Product Name: ISOXAZOLE-5-CARBOXYLIC ACID
• Synonyms: TIMTEC-BB SBB004319;AKOS PAO-1371;ISOXAZOLE-5-CARBOXYLIC ACID;BUTTPARK 27\08-41;5-Isoxazolecarboxylic acid;Isoxazole-5-carboxylic acid 98%;Isoxazole-5-carboxylic acid ,98%;5-Carboxyisoxazole, 1,2-Oxazole-5-carboxylic acid, 5-Carboxy-1,2-oxazole
• CAS NO: 21169-71-1
• Molecular Formula: C₄H₃NO₃
• Molecular Weight: 113.07
• Product Categories: Oxazole&Isoxazole;Building Blocks;Heterocyclic Building Blocks;Isoxazoles;carboxylic acid
• Mol File: 21169-71-1.mol

Chemical Properties

• Melting Point: 144-148 °C(lit.)
• Boiling Point: 211.74°C (rough estimate)
• Flash Point: 148.1 °C
• Appearance: Slightly yellow/Powder
• Density: 1.5808 (rough estimate)
• Vapor Pressure: 0.000125mmHg at 25°C
• Refractive Index: 1.4543 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.29±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: ISOXAZOLE-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ISOXAZOLE-5-CARBOXYLIC ACID(21169-71-1)
• EPA Substance Registry System: ISOXAZOLE-5-CARBOXYLIC ACID(21169-71-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-25-24-36-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 21169-71-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Isoxazole-5-carboxylic acid is used as a key intermediate in the synthesis of acylguanidine FXa inhibitors for the pharmaceutical industry. These inhibitors play a vital role in the treatment of various medical conditions, such as blood clotting disorders and other related health issues. The compound's ability to participate in the synthesis process makes it a valuable asset in the development of new and effective medications.
Used in Chemical Synthesis:
Isoxazole-5-carboxylic acid is also used as a reagent in the synthesis of various chemical compounds. Its unique properties allow it to be involved in conjugate addition reactions, which are essential in the formation of isoxazole-5-carboxylic acid derivatives. These derivatives can be further utilized in the development of new chemicals and materials with potential applications in various industries.
Used in Research and Development:
Isoxazole-5-carboxylic acid is employed as a research compound in the study of isoxazoles and their chemical properties. Its involvement in the synthesis and reactivity of isoxazoles makes it an important tool for scientists and researchers working on the development of new compounds and materials. The compound's versatility in chemical reactions allows researchers to explore its potential applications in various fields, including pharmaceuticals, materials science, and more.

InChI:InChI=1/C4H3NO3/c6-4(7)3-1-2-5-8-3/h1-2H,(H,6,7)

Upstream product

• 98019-60-4 5-(hydroxymethyl)isoxazole 
• 88511-38-0 1-(isoxazole-5-yl)ethanone 
• 30192-57-5 isoxazole-5-carbaldehyde oxime 
• 34648-11-8 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole 
• 5765-44-6 5-methylisoxazole 
• 59938-07-7 (3E)-1,1,1-trichloro-4-ethoxybut-3-en-2-one 
• 88283-10-7 5-trichloromethyl isoxazole 
• 288-14-2 ISOXAZOLE 
• 124-38-9 carbon dioxide 

Downstream Products

• 15055-81-9 methyl 1,2-oxazole-5-carboxylate 
• 89032-77-9 isoxazole-5-carboxamide 
• 62348-13-4 isooxazole-5-carbonyl chloride 
• 173850-41-4 5-isoxazolecarboxylic acid ethyl ester 

Relevant articles and documents

CARBOXYLATION CATALYSTS

The use of a complex of the form Z—M—OR in the carboxylation of a substrate is described. The group Z is a two-electron donor ligand, M is a metal and OR is selected from the group consisting of OH, alkoxy and aryloxy. The substrate may be carboxylated at a C—H or N—H bond. The metal M may be copper, silver or gold. The two-electron donor ligand may be a phosphine, a carbene or a phosphite ligand. Also described are methods of manufacture of the complexes and methods for preparing isotopically labelled caboxylic acids and carboxylic acid derivatives.

Carboxylation of C-H bonds using N -heterocyclic carbene gold(I) complexes

A highly efficient [(NHC)AuI]-based (NHC = N-heterocyclic carbene) catalytic system for the carboxylation of aromatic and heteroaromatic C-H bonds was developed. The significant base strength of the Au-OH species is at the origin of the activation process and permits the facile functionalization of C-H bonds without the use of other organometallic reagents.

A convenient one-pot synthesis of 5-carboxyisoxazoles: Trichloromethyl group as a carboxyl group precursor

The one-pot synthesis of ten 5-carboxyisoxazoles from the cyclocondensation of β-alkoxyvinyl trichloromethyl ketones [CCl3C(O)C(R2)=C(R1)OR, where R1, R2=H, Me and R=Me, Et] and 2- trichloroacetyl cyclohexanone with hydroxylamine is reported. This work shows that the trichloromethyl group attached to β-alkoxyvinyl trichloromethyl ketones (a heterocyclic CCC building block) is an excellent carboxyl group precursor.

Chemical oxidation of an anticonvulsant N-(5'-methylisoxazol-3-yl) 2,6- dimethylbenzamide (D2916)

The new anticonvulsant N-(5'-methylisoxazol-3-yl)-2,6-dimethylbeazamide (D2916), which presents two kinds of methyl groups which could be oxidized, was submitted to various chemical oxidizing agents. Several sites and degrees of oxidation were observed. The main oxidized site was the arylmethyl group without cleavage of the isoxazole ring, leading via carboxylic acid and primary alcohol intermediates to phthalimide and lactame derivatives. In no case was the methyl group of the isoxazole moiety hydroxylated.