Dibenzothiophene-5-oxide

• CAS: 1013-23-6
• Catalog Number: ACM1013236
• Category: Main Products
• Molecular Weight: 200.25632
• Molecular Formula: C₁₂H₈OS
• Synonyms: Dibenzothiophene-5-oxide;javascript:showMsgDetail(ProductSynonyMs.aspxCBN
• IUPAC Name: dibenzothiophene5-oxide
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3S2=O
• InChI Key: NGDPCAMPVQYGCW-UHFFFAOYSA-N
• Boiling Point: 400.8ºC at 760mmHg
• Flash Point: 196.2ºC
• Density: 1.41g/cm³
• Exact Mass: 200.03000

Case Study

Synthesis of 4-Substituted Dibenzothiophenes from Dibenzothiophene-5-Oxide

Hu, Xiaofang, et al. Organic & Biomolecular Chemistry, 2023, 21(46), 9123-9127.

The synthesis of 4-substituted dibenzothiophenes (DBT) from dibenzothiophene-5-oxide (DBTO) can be achieved using a one-pot method. The method involves a sulfoxide-guided C-H metallation/boration/B2Pin2-mediated reduction/Suzuki coupling process. A variety of DBT-based heterobiaryl compounds were successfully prepared using DBTO as a model substrate.
Synthesis of DBT compounds from DBTO
· Optimal reaction conditions: DBTO (0.2 mmol), LiHMDS base (6.0 eq.), B2Pin2 (5.0 eq.), THF (1.2 mL), at 55 °C under Ar atmosphere for 13 h.
· Aryl halides with electron-withdrawing groups (including NO2, aldehydes, and ketones) at the ortho, meta, and para positions afforded the corresponding Suzuki coupling products in 35% to 76% yield.
· 1-tert-butyl-4-iodobenzene and 2-iodoanisole were also successfully converted into 4-aryl-substituted DBT products, with yields of 79% and 54%, respectively.
· The luminescent material PhImPOTD 39 was successfully synthesized through the reaction of DBTO and PhImPOI through a one-pot two-step method with a yield of 62%.

Custom Reviews

August 14, 2023

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Unique optical raw materials
The structure of dibenzothiophene-5-oxide enables it to obtain compounds with various optical properties through chemical modification.

Custom Q&A

What is the molecular structure of dibenzothiophene-5-oxide ?

C12H8OS

What are the storage conditions for dibenzothiophene-5-oxide ?

Dibenzothiophene-5-oxide should be stored in a dark, airtight and dry place at room temperature.

How soluble is dibenzothiophene-5-oxide in organic reagents ?

Dibenzothiophene-5-oxide is slightly soluble in chloroform and methanol

How to prepare to get dibenzothiophene 5-oxide ?

Dibenzothiophene is reacted by heating it in an oxygen atmosphere; common reaction conditions include high temperature and high pressure. By fully contacting dibenzothiophene with oxygen, an oxidation reaction can occur to form dibenzothiophene 5-oxide.

What are the relevant applications of dibenzothiophene 5-oxide ?

Dibenzothiophene 5-oxide can be used as a starting material or intermediate in organic synthesis to build complex organic molecules. And since dibenzothiophene 5-oxides and their derivatives may have potential pharmaceutical activities, they may also be used in pharmaceutical research and development to find new drug candidates for the treatment of various diseases. In addition dibenzothiophene 5-oxides have good electron transport properties and photophysical properties, which can be used in the construction of organic optoelectronic devices such as organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs) and organic solar cells (OPVs).

What is the molecular mass of dibenzothiophene 5-oxide ?

200.26

What is the PSA of dibenzothiophene 5-oxide ?

38.77

What is the refractive index of dibenzothiophene 5-oxide ?

1.761

What is the InChIKey of dibenzothiophene 5-oxide ?

NGDPCAMPVQYGCW-UHFFFAOYSA-N

What is the SMILES of dibenzothiophene 5-oxide ?

C1=CC=C2C(=C1)C3=CC=CC=C3S2=O

Synthetic Use

Upstream Synthesis Route 1

• 132-65-0

• 1013-23-6

Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 12, p. 2009 - 2012

Upstream Synthesis Route 2

• 132-65-0

• 1013-23-6
• 1016-05-3

Reference: [1] Synlett, 2015, vol. 26, # 18, p. 2547 - 2552

Upstream Synthesis Route 3

• 74-88-4

• 1013-23-6

Reference: [1] Journal of the American Chemical Society, 1981, vol. 103, # 2, p. 289 - 295

Upstream Synthesis Route 4

• 132-65-0

• 1013-23-6

Reference: [1]Bahrami
[Tetrahedron Letters, 2006, vol. 47, # 12, p. 2009 - 2012]

Upstream Synthesis Route 5

• 132-65-0

• 1013-23-6
• 1016-05-3

Reference: [1]Bresciani, Giulio; Ciancaleoni, Gianluca; Crucianelli, Marcello; Gemmiti, Mario; Marchetti, Fabio; Pampaloni, Guido
[Molecular catalysis, 2021, vol. 516]

Downstream Synthesis Route 1

• 1013-23-6

• 132-65-0

Reference: [1]Fujiki, Kiyoko; Kurita, Shigehito; Yoshida, Eiji
[Synthetic Communications, 1996, vol. 26, # 19, p. 3619 - 3626]

* For details of the synthesis route, please refer to the original source to ensure accuracy.