Benzothioxanthene dicarboxylic anhydride

• CAS: 14121-49-4
• Catalog Number: ACM14121494
• Category: Main Products
• Molecular Weight: 304.3
• Molecular Formula: H18H8O3S
• Synonyms: 4,10-benzothioxanthene-3,1-dicarboxylic acid anhydride; benzothioxanthenedicarboxylic acid anhydride; benzo[kl]thioxanthene-3,4-dicarboxylic acid anhydride; 1h,3h-thioxantheno[2,1,9-def]-2-benzopyran-1,3-dione; benzothioxanthene-3,4-dicarboxylic anhydride; thioxantheno[2,1,9-def]isochromene-1,3-dione; BENZOTHIOANTHENEDICARBOXYLICANHYDRIDE; 1H,3H-2-Oxa-6-thiabenzo[a]pyrene-1,3-dione; thioxantheno[2,1,9-dej]isochromene-1,3-dione;
• IUPAC Name: Benzothioxanthene dicarboxylic anhydride
• Canonical SMILES: C1=CC=C2C(=C1)C3=C4C(=CC=C5C4=C(C=C3)C(=O)OC5=O)S2
• InChI Key: YCJAUMBAFBAMFV-UHFFFAOYSA-N
• Boiling Point: 602.1ºC at 760mmHg
• Flash Point: 331.4ºC
• Density: 1.56g/cm³
• Exact Mass: 304.01900

Case Study

Synthesis of Organic Fluorescent Dye from Benzothioxanthene Dicarboxylic Anhydride for Layered Silicate Labeling

Danko, Martin, et al. Chemical Papers, 2013, 67, 18-28.

By condensing 3-(triethoxysilyl)-1-propanamine (3-aminopropyltriethoxysilane) with 4,10-benzothioxanthene-3,1'-dicarboxylic acid anhydride (BTXA) and N,N-dimethylaminonaphthalene-1,8-dicarboxylic acid anhydride (DMANA), new fluorescence dyes with an alkoxysilane moiety were developed by an imidic bridge. The fluorescent silane dyes were bonded to the surface of layered silicate microscopic particles and SiO2 wafers, and can be used for layered silicate labelling.
Synthesis of BTX-S fluorescent dye from BTXA
· The reaction was conducted in a Schlenk flask fitted with an argon balloon and a septum. A total of 0.2 g (0.66 mmol) of BTXA was introduced into the flask and dried for 2 hours under vacuum. APTES (1 mL, 4 mmol) was subsequently added to the flask through the septum using a syringe, all while maintaining an argon atmosphere.
· The reaction mixture was then heated to a temperature of (150 ± 5)°C in an oil bath for a period of 5 hours. Once cooled to room temperature, the resulting solid product was washed five times with dry cyclohexane via a vacuum line to eliminate excess soluble APTES.
· During each washing step, the solvent was extracted using a syringe and needle through the septum. After drying on a vacuum line for 5 hours, the final product, N-(3-(triethoxysilyl)propyl)-thioxantheno[2,1,9-dej] isoquinoline-1,3-dione (BTX-S), was isolated as an orange-yellow solid residue, achieving an approximate yield of 75%.

Synthesis of Monobrominated Benzothioxanthene Derivatives from Benzothioxanthene Dicarboxylic Anhydride

Josse, Pierre, et al. Journal of Materials Chemistry C, 2018, 6(4), 761-766.

The monobrominated benzothioxanthene (Br-BTXI) derivatives can be used in palladium-catalyzed coupling reactions and conjugated semiconductors for organic electronic applications. Herein, an efficient route for the synthesis of brominated BTXI starting from benzothioxanthene dicarboxylic anhydride (BTXA) was reported.
Synthesis procedure of Br-BTXI from BTXA
· 2-(pentan-3-yl)-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione (1, BTXI): In a 100 mL round-bottom flask with a condenser, 500 mg (1.64 mmol) of 1H,3H-thioxantheno[2,1,9-def]isochromene-1,3-dione, 157 mg (1.81 mmol) of 3-aminopentane, and 5 g of imidazole were mixed and heated at 100 °C for five hours. Once it had been room-cooled, 1M HCl was added and the liquid extracted with dichloromethane. The organic crust was washed with water and brine and dried with MgSO4. It was purified by silica gel column chromatography with a petroleum ether:dichloromethane (3:7 v/v) eluent, and the crude was cleaned up by distillation by rotary evaporation. The end result was obtained in a yield of 70% (434 mg).
· 5-bromo-2-(pentan-3-yl)-1H-thioxantheno[2,1,9-def]isoquinoline-1,3(2H)-dione (2, Br-BTXI): Solution of BTXI (500 mg, 1.34 mmol) in 100 mL of dichloromethane was dropwise addition of a solution of bromine solution in dichloromethane (214 mg, 1.34 mmol, 1M). The reaction solution was stirred at room temperature for 12 hours, then washed down with dissolved Na2S2O3, water and brine. The solvent was evaporated by drying it on MgSO4 and the solution, which was purified by silica gel column chromatography, was used as eluent with dichloromethane. This was picked in a 93% (568 mg) production.