3-Bromo-5-phenyl-4,5-dihydroisoxazole

Base Information

• Chemical Name: 3-Bromo-5-phenyl-4,5-dihydroisoxazole
• CAS No.: 86256-88-4
• Molecular Formula: C9H8BrNO
• Molecular Weight: 226.073
• Hs Code.: 2934999090
• ChEMBL ID: CHEMBL3329247
• DSSTox Substance ID: DTXSID50530226
• Nikkaji Number: J582.134G
• Mol file: 86256-88-4.mol

Synonyms:3-Bromo-5-phenyl-4,5-dihydroisoxazole;86256-88-4;3-bromo-5-phenyl-4,5-dihydro-1,2-oxazole;3-bromo-5-phenylisoxazoline;SCHEMBL1169872;CHEMBL3329247;LNXKJBBQEFYTQV-UHFFFAOYSA-;DTXSID50530226;LNXKJBBQEFYTQV-UHFFFAOYSA-N;MFCD11707003;AKOS015836087;BS-24210;PD139239;CS-0207655;3-Bromo-5-phenyl-4,5-dihydroisoxazole 95+%;A917661;3-Bromo-5-phenyl-4,5-dihydroisoxazole, AldrichCPR;J-512054;InChI=1/C9H8BrNO/c10-9-6-8(12-11-9)7-4-2-1-3-5-7/h1-5,8H,6H2

Chemical Property of 3-Bromo-5-phenyl-4,5-dihydroisoxazole

Chemical Property:

• Vapor Pressure: 0.005mmHg at 25°C
• Boiling Point: 283.845oC at 760 mmHg
• Flash Point: 125.465oC
• PSA: 21.59000
• Density: 1.569g/cm3
• LogP: 2.29200
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 224.97893
• Heavy Atom Count: 12
• Complexity: 187

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo-5-phenyl-4,5-dihydroisoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(ON=C1Br)C2=CC=CC=C2

Technology Process of 3-Bromo-5-phenyl-4,5-dihydroisoxazole

There total 5 articles about 3-Bromo-5-phenyl-4,5-dihydroisoxazole 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: 99.0%

cis-1-bromo-2-phenylcyclopropane (32523-76-5) → 3-bromo-4,5-dihydro-5-phenyl-isoxazole (86256-88-4)

Guidance literature:

With nitrosyl chloride sulfur trioxide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1134/S1070428009020110

Reference yield: 95.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + N-dibromomethylidenehydroxylamine (74213-24-4) → 3-bromo-4,5-dihydro-5-phenyl-isoxazole (86256-88-4)

Guidance literature:

With potassium hydrogencarbonate; In water; N,N-dimethyl-formamide; at -10 - 20 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol9000284

Reference yield: 34.0%

1-bromo-2-phenylcyclopropane (36617-02-4) → 3-bromo-4,5-dihydro-5-phenyl-isoxazole (86256-88-4) + 4-bromo-5-phenylisoxazoline (90712-70-2)

Guidance literature:

With sodium nitrite; In chloroform; trifluoroacetic acid; at -5 ℃; for 0.5h; Product distribution;

DOI:10.1007/BF00515629

upstream raw materials:

styrene

N-dibromomethylidenehydroxylamine

1-bromo-2-phenylcyclopropane

cis-1-bromo-2-phenylcyclopropane

Downstream raw materials:

2-ethyl-5-phenylisoxazolidin-3-one

2-methyl-5-phenylisoxazolidin-3-one

3-hydroxy-3-phenylpropanenitrile

butyl 3-(trichlorovinyl)-4,5-dihydroisoxazole-5-carboxylate

Refernces

• 1、 Probst,Deprez,Willand. "Palladium-free Sonogashira-type cross-coupling reaction of bromoisoxazolines or N-alkoxyimidoyl bromides and alkynes". supporting information. p. 1066 - 1070. Retrieved 2018/03/26.
• 2、 J?st, Christian,Nitsche, Christoph,Scholz, Therese,Roux, Lionel,Klein, Christian D.. "Promiscuity and selectivity in covalent enzyme inhibition: A systematic study of electrophilic fragments". supporting information. p. 7590 - 7599. Retrieved 2014/12/11.