2-Methylbenzo[b]thiophene 1-oxide

Base Information

• Chemical Name: 2-Methylbenzo[b]thiophene 1-oxide
• CAS No.: 33945-86-7
• Molecular Formula: C9H8OS
• Molecular Weight: 164.228
• DSSTox Substance ID: DTXSID80955524
• Nikkaji Number: J1.727.940H
• Mol file: 33945-86-7.mol

Synonyms:2-Methylbenzo[b]thiophene 1-oxide;33945-86-7;2-Methylbenzo(b)thiophene 1-oxide;2-methylbenzothiophene 1-oxide;DTXSID80955524;2-Methyl-1H-1-benzothiophen-1-one;Benzo[b]thiophene, 2-methyl-, 1-oxide

Chemical Property of 2-Methylbenzo[b]thiophene 1-oxide

Chemical Property:

• Vapor Pressure: 0.219mmHg at 25°C
• Refractive Index: 1.452
• Boiling Point: 373.781 °C at 760 mmHg
• Flash Point: 179.857 °C
• Density: 1.326 g/cm³
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 164.02958605
• Heavy Atom Count: 11
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=CC=CC=C2S1=O

Technology Process of 2-Methylbenzo[b]thiophene 1-oxide

There total 4 articles about 2-Methylbenzo[b]thiophene 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: 95.0%

2-Methylbenzothiophene (1195-14-8) → 2-Methylbenzothiophene sulfoxide (33945-86-7)

Guidance literature:

With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2020.131315

Reference yield: 25.0%

2-Methylbenzothiophene (1195-14-8) → 2-Methylbenzothiophene sulfoxide (33945-86-7) + (+)-2-methyl-(4R,5S)-cis-4,5-dihydroxy-4,5-dihydrobenzo[b]thiophene (1397698-17-7) + 2-methyl-2,3-dihydroxy-2,3-dihydrobenzo[b]thiophene + 2-methyl-2,3-dihydroxy-2,3-dihydrobenzo[b]thiophene

Guidance literature:

With toluene dioxygenase from Pseudomonas putida UV₄; optical yield given as %ee; Enzymatic reaction;

DOI:10.1039/c2ob26120k

Reference yield: 10.0%

2-Methylbenzothiophene (1195-14-8) → 2-methylbenzothiophene S,S-dioxide (6224-55-1) + 2-Methylbenzothiophene sulfoxide (33945-86-7)

Guidance literature:

With dihydrogen peroxide; C₂₂H₄₄N₆Nb₂O₁₄; In water; acetonitrile; at 45 ℃; for 3.5h; Catalytic behavior; Inert atmosphere; Sealed tube;

DOI:10.1016/j.mcat.2021.111972

upstream raw materials:

2-Methylbenzothiophene

Downstream raw materials:

8-oxo-8a-methyl-2,3-diphenyl-2,3-dihydrobenzothieno<3,2-d>isoxazolidine

4-oxo-3a-methyl-2,3-diphenyl-2,3-dihydrobenzothieno<2,3-d>isoxazolidine

2-Methylbenzothiophene

Refernces

• 1、 Bresciani, Giulio,Ciancaleoni, Gianluca,Crucianelli, Marcello,Gemmiti, Mario,Marchetti, Fabio,Pampaloni, Guido. "Niobium(V) oxido tris-carbamate as easily available and robust catalytic precursor for the selective sulfide to sulfone oxidation". . . Retrieved 2021/11/01.
• 2、 ?iau?iulis, Mindaugas,Ahlsten, Nanna,Pulis, Alexander P.,Procter, David J.. "Transition-Metal-Free Cross-Coupling of Benzothiophenes and Styrenes in a Stereoselective Synthesis of Substituted (E,Z)-1,3-Dienes". supporting information. p. 8779 - 8783. Retrieved 2019/06/19.