3H-Indol-3-one, 6-chloro-2-phenyl-, 1-oxide

Base Information

• Chemical Name: 3H-Indol-3-one, 6-chloro-2-phenyl-, 1-oxide
• CAS No.: 74625-87-9
• Molecular Formula: C14H8ClNO2
• Molecular Weight: 257.676
• DSSTox Substance ID: DTXSID60457677
• Wikidata: Q82280618
• Mol file: 74625-87-9.mol

Synonyms:3H-Indol-3-one, 6-chloro-2-phenyl-, 1-oxide;74625-87-9;DTXSID60457677

Chemical Property of 3H-Indol-3-one, 6-chloro-2-phenyl-, 1-oxide

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 257.0243562
• Heavy Atom Count: 18
• Complexity: 387

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=[N+](C3=C(C2=O)C=CC(=C3)Cl)[O-]

Technology Process of 3H-Indol-3-one, 6-chloro-2-phenyl-, 1-oxide

There total 7 articles about 3H-Indol-3-one, 6-chloro-2-phenyl-, 1-oxide 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: 72.0%

3-(4-Chloro-2-nitro-phenyl)-3-oxo-2-phenyl-propionaldehyde (74599-01-2) → 6-Chloro-1-oxy-2-phenyl-indol-3-one (74625-87-9) + 1-(4-Chloro-2-nitro-phenyl)-2-phenyl-ethanone (85636-81-3)

Guidance literature:

With sodium acetate; In ethanol; water; Heating;

Reference yield:

4-chloro-2-nitro-1-(phenylethynyl)benzene → 6-Chloro-1-oxy-2-phenyl-indol-3-one (74625-87-9)

Guidance literature:

With gold(III) chloride; In 1,2-dichloro-ethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02035

Reference yield:

4-chloro-2-nitro-1-(phenylethynyl)benzene → 6-Chloro-1-oxy-2-phenyl-indol-3-one (74625-87-9) + (6-chlorobenzo[c]isoxazol-3-yl)(phenyl)methanone

Guidance literature:

With gold(III) tribromide; In toluene; at 4 ℃; for 2h;

DOI:10.1016/S0040-4039(03)01357-1

upstream raw materials:

3-(4-Chloro-2-nitro-phenyl)-3-oxo-2-phenyl-propionaldehyde

4'-chloro-2'-nitroacetophenone

(E)-1-(4-Chloro-2-nitro-phenyl)-3-phenyl-propenone

(4-chloro-2-nitrophenyl)(3-phenyloxiran-2-yl)methanone

Downstream raw materials:

C₂₃H₁₇ClN₂O₂

C₂₂H₁₅ClN₂O₂

Refernces

• 1、 Dhote, Pawan S.,Ramana, Chepuri V.. "One-Pot Au[III]-/Lewis Acid Catalyzed Cycloisomerization of Nitroalkynes and [3 + 3]Cycloaddition with Donor-Acceptor Cyclopropanes". supporting information. p. 6221 - 6224. Retrieved 2019/08/26.
• 2、 Sahasrabudhe, A. B.,Kamath, H. V.,Bapat, B. V.,Kulkarni, Sheshgiri N.. "Antitubercular Agents : Part III - Synthesis of Substituted 2-Arylisatogens". . p. 230 - 232. Retrieved 2007/10/02.