5-Phenylisoxazole-3-carbonyl chloride

Base Information

• Chemical Name: 5-Phenylisoxazole-3-carbonyl chloride
• CAS No.: 78189-50-1
• Molecular Formula: C10H6 Cl N O2
• Molecular Weight: 207.616
• Hs Code.: 2934999090
• European Community (EC) Number: 692-403-9
• DSSTox Substance ID: DTXSID50428174
• Wikidata: Q82240972
• Mol file: 78189-50-1.mol

Synonyms:5-PHENYLISOXAZOLE-3-CARBONYL CHLORIDE;78189-50-1;5-phenyl-1,2-oxazole-3-carbonyl chloride;5-Phenyl-isoxazole-3-carbonyl chloride;SCHEMBL892678;DTXSID50428174;FUQOIZJIDZZDGY-UHFFFAOYSA-N;5-Phenylisoxazole-3-carbonylchloride;MFCD07772806;AKOS015840545;AS-5888;FT-0682818;EN300-238061;A865082;F2190-0154

Chemical Property of 5-Phenylisoxazole-3-carbonyl chloride

Chemical Property:

• Vapor Pressure: 1.12E-05mmHg at 25°C
• Melting Point: 86 °C
• Refractive Index: 1.568
• Boiling Point: 370.2°C at 760 mmHg
• PKA: -7.72±0.28(Predicted)
• Flash Point: 177.7°C
• PSA: 43.10000
• Density: 1.321g/cm³
• LogP: 2.72060
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 207.0087061
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

98%min ^*data from raw suppliers

5-Phenyl-isoxazole-3-carbonylchloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=NO2)C(=O)Cl

Technology Process of 5-Phenylisoxazole-3-carbonyl chloride

There total 12 articles about 5-Phenylisoxazole-3-carbonyl chloride 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:

Reference yield: 98.0%

5-phenyl-3-isoxazolecarboxylic acid (14441-90-8) → 5-phenylisoxazole-3-carboxylic acid chloride (78189-50-1)

Guidance literature:

With thionyl chloride; for 4h; Reflux;

DOI:10.1134/S1070428012010216

Reference yield:

(E)-5-phenyl-3-(2-phenylethenyl)-2-isoxazoline (107487-07-0) → 5-phenylisoxazole-3-carboxylic acid chloride (78189-50-1) + benzoyl chloride (98-88-4)

Guidance literature:

(E)-5-phenyl-3-(2-phenylethenyl)-2-isoxazoline; With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; In water; for 1h; Sealed tube;

With water; sodium hydroxide; at 80 ℃; for 10h; Sealed tube;

With thionyl chloride; for 2h; Reflux;

DOI:10.1039/c8gc00630j

Reference yield:

(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one oxime (6502-37-0) → 5-phenylisoxazole-3-carboxylic acid chloride (78189-50-1) + benzoyl chloride (98-88-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper diacetate; sodium sulfate; pyridine / 1,2-dichloro-ethane / 12 h / 25 °C

2.1: iron(III) chloride hexahydrate; 1,10-Phenanthroline / tetrahydrofuran / 80 °C / Inert atmosphere; Sealed tube

3.1: tert.-butylhydroperoxide; iron(III) chloride hexahydrate / water / 1 h / Sealed tube

3.2: 10 h / 80 °C / Sealed tube

3.3: 2 h / Reflux

With pyridine; tert.-butylhydroperoxide; 1,10-Phenanthroline; iron(III) chloride hexahydrate; copper diacetate; sodium sulfate; In tetrahydrofuran; water; 1,2-dichloro-ethane;

DOI:10.1039/c8gc00630j

upstream raw materials:

ethyl 5-phenylisoxazole-3-carboxylate

5-phenyl-3-isoxazolecarboxylic acid

3-hydroxyiminomethyl-5-phenylisoxazole

5-phenylisoxazole-3-carbonitrile

Downstream raw materials:

5-formyl-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate

2-ethoxy-4-formylphenyl 5-phenylisoxazole-3-carboxylate

(E)-4-(biphenyl-4-yliminomethyl)phenyl 5-phenylisoxazole-3-carboxylate

(E)-4-(2-hydroxyphenyliminomethyl)phenyl 5-phenylisoxazole-3-carboxylate

Refernces

• 1、 Linciano, Pasquale,Pinzi, Luca,Belluti, Silvia,Chianese, Ugo,Benedetti, Rosaria,Moi, Davide,Altucci, Lucia,Franchini, Silvia,Imbriano, Carol,Sorbi, Claudia,Rastelli, Giulio. "Inhibitors of histone deacetylase 6 based on a novel 3-hydroxy-isoxazole zinc binding group". . p. 2080 - 2086. Retrieved 2021/10/02.
• 2、 Potkin,Petkevich,Kletskov,Zubenko,Kurman,Pashkevich,Gurinovich,Kulchitskiy. "The synthesis of isoxazolyl- and isothiazolylcarbamides exhibiting antitumor activity". . p. 1667 - 1676. Retrieved 2015/02/02.