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12H-Benzo[b]phenothiazine, also known as NSC81120, is a versatile compound that exhibits a strong preference for cross-dehydrogenative C-C bond-forming reactions, distinguishing it from phenothiazines, which typically favor amination reactions. Its reactivity enables the formation of diverse oxidative coupling products, including unique indole-fused paddlewheel-like structures. Additionally, derivatives such as phenyl benzo[b]phenothiazine (Ph-benzoPTZ) have been utilized as effective visible light photoredox catalysts in metal-free atom transfer radical polymerization (ATRP), facilitating controlled polymerization of methacrylate monomers.

258-08-2

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258-08-2 Usage

Chemical structure

Tricyclic structure containing a benzene ring fused to a phenothiazine ring system.

Usage

Starting material in the synthesis of various drugs with pharmaceutical applications.

Drug applications

Antipsychotics and antihistamines.

Potential properties

Anti-cancer properties.

Target

Cellular signaling pathways involved in tumor growth and progression.

Additional properties

Antioxidant and neuroprotective properties.

Potential applications

Treating neurodegenerative diseases and oxidative stress-related conditions.

Research status

Further research needed to fully understand therapeutic potential and mechanisms of action.

Check Digit Verification of cas no

The CAS Registry Mumber 258-08-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,5 and 8 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 258-08:
(5*2)+(4*5)+(3*8)+(2*0)+(1*8)=62
62 % 10 = 2
So 258-08-2 is a valid CAS Registry Number.

258-08-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 12H-Benzo[b]phenothiazine

1.2 Other means of identification

Product number -
Other names Benzo-ss-thiodiphenylamin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:258-08-2 SDS

258-08-2Relevant academic research and scientific papers

Benzophenothiazine and Its Cr(III)-Catalyzed Cross Dehydrogenative Couplings

Bub, Christina L.,Th?nni?en, Vinzenz,Patureau, Frederic W.

, p. 9196 - 9198 (2020)

In stark contrast to phenothiazines and their prevalence for cross-dehydrogenative amination reactions, benzophenothiazine has a pronounced preference for cross-dehydrogenative C-C bond-forming reactions. Moreover, the substrate is very versatile, leading to several new classes of C-C bond-forming reactions and many new oxidative coupling product architectures, including unprecedented indole fused paddlewheel-like structures.

Phenyl Benzo[b]phenothiazine as a Visible Light Photoredox Catalyst for Metal-Free Atom Transfer Radical Polymerization

Dadashi-Silab, Sajjad,Pan, Xiangcheng,Matyjaszewski, Krzysztof

, p. 5972 - 5977 (2017)

This paper reports use of phenyl benzo[b]phenothiazine (Ph-benzoPTZ) as a visible light-induced metal-free atom transfer radical polymerization (ATRP) photoredox catalyst. Well-controlled polymerizations of various methacrylate monomers were conducted und

N -Arylbenzo[ b ]phenothiazines as Reducing Photoredox Catalysts for Nucleophilic Additions of Alcohols to Styrenes: Shift towards Visible Light

Seyfert, Fabienne,Wagenknecht, Hans-Achim

supporting information, p. 582 - 586 (2021/01/25)

N -Phenylphenothiazines are an important class of photoredox catalysts because they are synthetically well accessible, they allow the tuning of the optoelectronic properties by different substituents, and they have strong reduction properties for activation of alkenes. One of the major disadvantages of N -phenylphenothiazines, however, is the excitation at 365 nm in the UV-A light range. We synthesized three differently dialkylamino-substituted N -phenylbenzo[ b ]phenothiazines as alternative photoredox catalysts and applied them for the nucleo philic addition of alkohols to α-methyl styrene. The additional benzene ring shift the absorbance bathochromically and allows performing the photocatalyses by excitation at 385 nm and 405 nm. This type of photoredox catalysis tolerates other functional groups, as representatively shown for alcohols as substrates with C-C and C-N triple bonds.

Synthesis of diverse phenothiazines by direct thioamination of arynes with S-(o-bromoaryl)-S-methylsulfilimines and subsequent intramolecular BuchwaldHartwig amination

Matsuzawa, Tsubasa,Uchida, Keisuke,Yoshida, Suguru,Hosoya, Takamitsu

, p. 825 - 828 (2018/07/05)

A facile method for the synthesis of diverse phenothiazines has been achieved by direct thioamination of aryne intermediates with S-(o-bromoaryl)-S-methylsulfilimines and subsequent intramolecular BuchwaldHartwig amination. Since various sulfilimines could be prepared easily by odorless copper-catalyzed ipso-thiolation of readily available o-bromoarylboronic acids followed by imination and hydrolysis, this approach enables the synthesis of a wide variety of multisubstituted phenothiazines.

Mechanism of Photoinduced Metal-Free Atom Transfer Radical Polymerization: Experimental and Computational Studies

Pan, Xiangcheng,Fang, Cheng,Fantin, Marco,Malhotra, Nikhil,So, Woong Young,Peteanu, Linda A.,Isse, Abdirisak A.,Gennaro, Armando,Liu, Peng,Matyjaszewski, Krzysztof

supporting information, p. 2411 - 2425 (2016/03/05)

Photoinduced metal-free atom transfer radical polymerization (ATRP) of methyl methacrylate was investigated using several phenothiazine derivatives and other related compounds as photoredox catalysts. The experiments show that all selected catalysts can b

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