Thianthrene 5-oxide

Base Information

• Chemical Name: Thianthrene 5-oxide
• CAS No.: 2362-50-7
• Molecular Formula: C12H8OS2
• Molecular Weight: 232.327
• Hs Code.: 2934999090
• European Community (EC) Number: 851-277-7
• NSC Number: 16859
• DSSTox Substance ID: DTXSID00178293
• Nikkaji Number: J104.352H
• Wikidata: Q83048680
• ChEMBL ID: CHEMBL529598
• Mol file: 2362-50-7.mol

Synonyms:thianthrene 5-oxide

Chemical Property of Thianthrene 5-oxide

Chemical Property:

• Vapor Pressure: 5.61E-07mmHg at 25°C
• Melting Point: 143-143.5 °C
• Refractive Index: 1.797
• Boiling Point: 423.2 °C at 760 mmHg
• Flash Point: 209.7 °C
• PSA: 61.58000
• Density: 1.49 g/cm³
• LogP: 4.18360
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 232.00165722
• Heavy Atom Count: 15
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

BENZOTHIANTHRENE OXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)SC3=CC=CC=C3S2=O
• Uses: Thianthrene S-oxide is a sulfoxide-based thianthrene reagent for late-stage C-H functionalization. Developed by the Ritter Lab, C-H functionalization by thianthrenation proceeds with >99% selectivity and furnishes functionalized arenes serving as synthetic linchpins for further participation in diverse transformations. Nonfluorinated thianthrene S-oxide is best used for all arenes more electron-rich than anisole. For other arenes, the fluorinated TFT S-oxide (903981) was demonstrated as the thanthrenation reagent.

Technology Process of Thianthrene 5-oxide

There total 87 articles about Thianthrene 5-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: 97.0%

5-Cycloheptyloxy-thianthren-5-ium; perchlorate → cycloheptyl bromide (2404-35-5) + thianthrene-5-oxide (2362-50-7) + cycloheptanol (502-41-0) + Thianthrene (92-85-3)

Guidance literature:

With 18-crown-6 ether; potassium bromide; Product distribution;

DOI:10.1002/(SICI)1099-1395(199911)12:11<827::AID-POC198>3.0.CO;2-E

Reference yield: 96.0%

5-Cycloheptyloxy-thianthren-5-ium; perchlorate → thianthrene-5-oxide (2362-50-7) + cycloheptanol (502-41-0) + Thianthrene (92-85-3)

Guidance literature:

With sodium thiophenolate; thiophenol; In acetonitrile; for 2h; Product distribution;

DOI:10.1002/(SICI)1099-1395(199911)12:11<827::AID-POC198>3.0.CO;2-E

Reference yield: 52.0%

5-(cis-4-methylcyclohexyloxy)thianthreniumyl perchlorate → thianthrene-5-oxide (2362-50-7) + 4-methylcyclohexene (591-47-9) + cis-4-methylcyclohexanol (7731-28-4) + Thianthrene (92-85-3)

Guidance literature:

With potassium iodide; In acetonitrile; for 2h; Product distribution;

DOI:10.1002/(SICI)1099-1395(199911)12:11<827::AID-POC198>3.0.CO;2-E

upstream raw materials:

p-methylbenzaldehyde oxime

thianthrene cation radical perchlorate

p-methoxyl benzaldoxime

2.6-dimethylphenol

Downstream raw materials:

2-[2-(butane-1-sulfinyl)-phenylsulfanyl]-benzoic acid

dibenzothiophene

thianthren-1-ylcarboxylic acid

2,2'-thiodibenzoic acid

Refernces

• 1、 Jones, Guilford,Huang, Bin,Griffin, Susan F.. "Electron-Transfer Photochemistry of Thianthrene. Nucleophile-Assisted Photooxidation to Sulfoxide". . p. 2035 - 2042. Retrieved 1993.
• 2、 Ando, Wataru,Kabe, Yoshio,Kobayashi, Shohei,Takyu, Choichi,Yamagishi, Akio,Inaba, Humio. "Formation of Sulfinyl Oxide and Singlet Oxygen in the Reaction of Thianthrene Cation Radical and Superoxide Ion". . p. 4526 - 4528. Retrieved 1980.
• 3、 Qian, Ding-Quan,Shine, Henry J.,Guzman-Jimenez, Ilse Y.,Thurston, John H.,Whitmire, Kenton H.. "Mono- and bisadducts from the addition of thianthrene cation radical salts to cycloalkenes and alkenes". . p. 4030 - 4039. Retrieved 2007/10/03.