3,5-Diphenylisoxazole-4-carbaldehyde

Base Information

• Chemical Name: 3,5-Diphenylisoxazole-4-carbaldehyde
• CAS No.: 89479-71-0
• Molecular Formula: C16H11NO2
• Molecular Weight: 249.269
• DSSTox Substance ID: DTXSID00523906
• Nikkaji Number: J1.447.342D
• Wikidata: Q82390328
• Mol file: 89479-71-0.mol

Synonyms:3,5-Diphenylisoxazole-4-carbaldehyde;89479-71-0;3,5-Diphenyl-1,2-oxazole-4-carbaldehyde;DTXSID00523906

Chemical Property of 3,5-Diphenylisoxazole-4-carbaldehyde

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 249.078978594
• Heavy Atom Count: 19
• Complexity: 295

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C(=NO2)C3=CC=CC=C3)C=O

Technology Process of 3,5-Diphenylisoxazole-4-carbaldehyde

There total 5 articles about 3,5-Diphenylisoxazole-4-carbaldehyde 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: 80.0%

Phenylpropargyl aldehyde (2579-22-8) + benzohydroximoyl chloride (698-16-8) → 3,5-diphenylisoxazole-4-carbaldehyde (89479-71-0)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 0.5h; Reagent/catalyst; Solvent; Time; regioselective reaction; Mechanism;

DOI:10.1016/j.tetlet.2016.01.019

Reference yield: 53.0%

benzonitrile oxide (873-67-6) + 3-phenyl-propenal (104-55-2) → 3,5-diphenylisoxazole-4-carbaldehyde (89479-71-0) + 4-formyl-4,5-dihydro-3,5-diphenylisoxazole (89479-70-9) + 3,4-diphenyl-4,5-dihydroisoxazole-5-carbaldehyde + ((4S,5S)-3,4-Diphenyl-4,5-dihydro-isoxazol-5-yl)-methanediol

Guidance literature:

In diethyl ether; at 0 - 5 ℃; for 48h;

DOI:10.1016/S0040-4020(00)00356-2

Reference yield:

benzaldehyde (100-52-7) → 3,5-diphenylisoxazole-4-carbaldehyde (89479-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydroxylamine hydrochloride; sodium carbonate / ethanol; water / 0.5 h / 20 °C / pH 8 - 9

2: N-chloro-succinimide / N,N-dimethyl-formamide / 1.75 h / 35 - 49 °C

3: triethylamine / toluene / 0.5 h / 20 °C

With N-chloro-succinimide; hydroxylamine hydrochloride; sodium carbonate; triethylamine; In ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2016.01.019

upstream raw materials:

(E)-3-phenylpropenal

benzonitrile oxide

3-phenyl-propenal

Phenylpropargyl aldehyde

Downstream raw materials:

(3,5-diphenyl-isoxazol-4-yl)-methanol

3,5-diphenyl-4-(3-phenyl-1,4,2-dioxazol-5-yl)isoxazole