21667-32-3

Basic information

• Product Name: 10H-Phenothiazine, 3,7-dibromo-
• CAS NO: 21667-32-3
• Molecular Formula: C12H7Br2NS
• Molecular Weight: 357.068
• Mol File: 21667-32-3.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 10H-Phenothiazine, 3,7-dibromo-(CAS DataBase Reference)
• NIST Chemistry Reference: 10H-Phenothiazine, 3,7-dibromo-(21667-32-3)
• EPA Substance Registry System: 10H-Phenothiazine, 3,7-dibromo-(21667-32-3)

Safety Data

• Hazardous Substances Data: 21667-32-3(Hazardous Substances Data)

Usage

Chemical class

Phenothiazine

Structural feature

Presence of two bromine atoms at the 3 and 7 positions of the phenothiazine ring

Potential applications

Medicinal chemistry, specifically in the development of new drugs

Pharmacological properties

Antipsychotic, antiemetic, and antihistaminic properties (due to the phenothiazine class)

Specific pharmacological activities

Introduction of bromine atoms may impart unique properties

Chemical and physical properties

Valuable building block in organic synthesis

Industrial and research purposes

Creation of novel molecules for various applications

Molecular weight

Approximately 342.2 g/mol (based on the molecular formula)

Appearance

Yellow to light brown crystalline solid (typical for phenothiazine derivatives)

Upstream product

• 1206715-29-8 3,7-dibromophenothiazin-5-ium perbromide 
• 92-84-2 10H-phenothiazine 
• 7726-95-6 bromine 
• 1207-71-2 sulfoxyde de phenothiazine 
• 21886-26-0 1,3,7,9-tetrabromo-10H-phenothiazine 5-oxide 
• 18621-99-3 1,3,7,9-tetrabromo-phenothiazine 
• 2031-31-4 3,7-dibromo-10H-phenothiazine 5-oxide 

Downstream Products

• 1160637-74-0 3,7-bis((E)-2-(pyridin-4-yl)vinyl)-10H-phenothiazine 

Relevant articles and documents

Boronate ester cross-linked PVA hydrogels for the capture and H2O2-mediated release of active fluorophores

A new set of PVA hydrogels were formed using the boronate ester fluorescent probe PF1 and the novel boronate fluorescent probe PT1 as the covalent crosslinkers. Treatment with aqueous H2O2 allowed triggered release of the fluorescent dye accompanied by complete dissolution of the hydrogel.

Characterisation of 3,7-dibromophenothiazin-5-ium perbromide and its use for enhancing latent fingerprints

Solutions were formulated by dissolving 3,7-dibromophenothiazin-5-ium perbromide in primary and secondary alcohols with pyridine as base. These solutions were used as dips for the enhancement of latent fingerprints. Treatment of 3,7-dibromophenothiazin-5-

[1]Benzothieno[3,2-b]benzothiophene-Based Organic Dyes for Dye-Sensitized Solar Cells

Three new metal-free organic dyes with the [1]benzothieno[3,2-b]benzothiophene (BTBT) π-bridge, having the structure donor-π-acceptor (D-π-A) and labeled as 19, 20 and 21, have been designed and synthesized for application in dye-sensitized solar cells (DSSC). Once the design of the π-acceptor block was fixed, containing the BTBT as the π-bridge and the cyanoacrylic group as the electron acceptor and anchoring unit, we selected three donor units with different electron-donor capacity, in order to assemble new chromophores with high molar extinction coefficients (?), whose absorption features well reflect the good performance of the final DSSC devices. Starting with the 19 dye, which shows a molar extinction coefficient ? of over 14,000 M-1 cm-1 and takes into account the absorption maximun at the longer wavelength, the substitution of the BFT donor unit with the BFA yields a great enhancement of absorptivity (molar extinction coefficient ? > 42,000 M-1 cm-1), until reaching the higher value (? > 69,000 M-1 cm-1) with the BFPhz donor unit. The good general photovoltaic performances obtained with the three dyes highlight the suitable properties of electron-transport of the BTBT as the π-bridge in organic chromophore for DSSC, making this very cheap and easy to synthesize molecule particularly attractive for efficient and low-cost photovoltaic devices.

Synthesis of substituted phenothiazines analogous to methylene blue by electrophilic and nucleophilic aromatic substitutions in tandem. A mechanistic perspective

3,7-Disubstituted phenothiazines analogous to methylene blue (1) were synthesized from phenothiazine (6) reacting first with an excess of bromine in acetic acid to give 3,7-dibromophenothiazin-5-ium bromide (8), according to a reaction sequence that involves two electrophilic aromatic substitutions and one oxidation. Subsequently, 8 reacting with diallylamine or allylmethylamine via two nucleophilic aromatic substitution steps gave 3,7-bis[di(2-propenyl)amino]phenothiazin-5-ium bromide (3) or 3,7-bis[methyl, (2-propenyl)amino]phenothiazin-5-ium bromide (4), compounds analogous to methylene blue. The choice of solvent for the second step is critically important as 3,7-dibromophenothiazin-5-ium bromide is very reactive and prone to irreversible oxidation, reduction, and ipso attack at the 3- and 7- positions. The best yields (~63%) for the methylene blue analogues 3 and 4 were obtained when CHCl3 or CH2Cl2 were employed as solvents for the nucleophilic aromatic substitution step. These solvents dissolve the methylene blue analogue products, but not 3,7-dibromophenothiazin-5-ium bromide.

HIGH TRIPLET YIELD PHENOTHIAZINE DONOR-ACCEPTOR COMPLEXES FOR PHOTOREDOX CATALYSIS

Phenothiazine compounds of Formula (I) are described herein. These compounds are useful as highly reducing organic photoredox catalysts. Suitable substrates for use with the compounds of Formula (I) include acrylates, styrene, acrylamides, acrylonitrile,