78189-50-1

Basic information

• Product Name: 5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE
• Synonyms: 5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE;3-Isoxazolecarbonyl chloride, 5-phenyl- (9CI)
• CAS NO: 78189-50-1
• Molecular Formula: C₁₀H₆ClNO₂
• Molecular Weight: 207.61
• Product Categories: ACIDHALIDE
• Mol File: 78189-50-1.mol
• Article Data: 10

Chemical Properties

• Melting Point: 86 °C
• Boiling Point: 370.2°C at 760 mmHg
• Flash Point: 177.7°C
• Appearance: /
• Density: 1.321g/cm³
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: 1.568
• PKA: -7.72±0.28(Predicted)
• CAS DataBase Reference: 5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE(78189-50-1)
• EPA Substance Registry System: 5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE(78189-50-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 78189-50-1(Hazardous Substances Data)

Usage

General Description

5-Phenylisoxazole-3-carbonyl chloride is a chemical compound with the molecular formula C10H6ClNO2. It is a derivative of isoxazole and is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. 5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE is a reactive acylating agent and is commonly used in organic synthesis for the introduction of the isoxazole-3-carbonyl group into organic molecules. It is also utilized in the preparation of heterocyclic compounds and can act as a versatile building block for the production of a wide range of biologically active compounds. 5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE is a highly reactive and toxic substance and should be handled with care in a controlled laboratory environment.

InChI:InChI=1/C10H6ClNO2/c11-10(13)8-6-9(14-12-8)7-4-2-1-3-5-7/h1-6H

Upstream product

• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 7063-99-2 ethyl 5-phenylisoxazole-3-carboxylate 
• 107487-07-0 (E)-5-phenyl-3-(2-phenylethenyl)-2-isoxazoline 
• 6502-37-0 (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one oxime 
• 14442-24-1 5-phenylisoxazole-3-carbonitrile 
• 90770-96-0 3-hydroxyiminomethyl-5-phenylisoxazole 
• 14441-90-8 5-phenyl-3-isoxazolecarboxylic acid 

Downstream Products

• 1363770-41-5 5-formyl-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-44-8 2-ethoxy-4-formylphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-56-2 (E)-4-(biphenyl-4-yliminomethyl)phenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-58-4 (E)-4-(2-hydroxyphenyliminomethyl)phenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-60-8 (E)-4-(biphenyl-4-yliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-62-0 (E)-4-(4-bromophenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-65-3 (E)-4-(2-hydroxyphenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-67-5 (E)-5-(biphenyl-4-yliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-69-7 (E)-5-(4-bromophenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-71-1 (E)-5-(2-hydroxyphenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-75-5 (E)-2-(biphenyl-4-yliminomethyl)-6-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-79-9 (E)-2-(4-bromophenyliminomethyl)-6-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-81-3 (E)-2-(2-hydroxyphenyliminomethyl)-6-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-84-6 (E)-4-(biphenyl-4-yliminomethyl)-2-ethoxyphenyl 5-phenylisoxazole-3-carboxylate 

Relevant articles and documents

Synthesis of 5-azolyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 5-azolyl-1,3,4-thiadiazol-2-amines based on derivatives of 5-arylisoxazole-3-carboxylic and 4,5-dichloroisothiazole-3-carboxylic acids

[Figure not available: see fulltext.] 2-Mercapto-1,3,4-triazoles and 2-amino-1,3,4-thiadiazoles were synthesized by successive transformations of 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carboxylic acids and their derivatives. The amino group of 5-(

Iron(iii)-catalyzed selective N-O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from: N -vinyl-α,β-unsaturated ketonitrones

An iron(iii)-catalyst controlled cyclization and selective N-O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines. The regioselectivity for cyclization of styrenyl groups in N-vinyl-α,β-unsaturated nitrones was completely different during the formation of pyridines and isoxazolines. A rational mechanism for the formation of pyridines and isoxazolines was proposed based on the further control experimental studies. The isoxazolines can be converted to a novel bidentate N-ligand over four steps and an epoxypyridine scaffold was obtained from N-vinyl nitrone when copper(ii) acetate in combination with the prepared bidentate N-ligand was used.

Synthesis of functionally substituted isoxazole and isothiazole derivatives

Acylation of benzene and toluene with 5-phenyl- and 5-(p-tolyl)isoxazole-3- carbonyl chlorides gave 5-phenyl(or p-tolyl)isoxazol-3-yl phenyl(or p-tolyl)ketones which were reduced to the corresponding alcohols with sodium tetrahydridoborate in propan-2-ol. Selective reduction of the carboxy group in 4,5-dichloroisothiazole-3-carboxylic acid was achieved by the action of BH 3, and the aldehyde group in 4-formyl-2-methoxyphenyl 5-arylisoxazole-3-carboxylates and 4,5-dichloroisothiazole-3-carboxylates was reduced to hydroxymethyl group with sodium triacetoxyhydridoborate in benzene. Acylation of the resulting hydroxymethyl derivatives with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides afforded the corresponding esters containing two azole fragments in their molecules.