503862-08-6

Basic information

• Product Name: 2,1,3-Benzothiadiazole, 4,7-bis(4-methoxyphenyl)-
• CAS NO: 503862-08-6
• Molecular Formula: C20H16N2O2S
• Molecular Weight: 348.425
• Mol File: 503862-08-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 189-192 °C
• Boiling Point: 538.2±50.0 °C(Predicted)
• Density: 1.253±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,1,3-Benzothiadiazole, 4,7-bis(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,1,3-Benzothiadiazole, 4,7-bis(4-methoxyphenyl)-(503862-08-6)
• EPA Substance Registry System: 2,1,3-Benzothiadiazole, 4,7-bis(4-methoxyphenyl)-(503862-08-6)

Safety Data

• Hazardous Substances Data: 503862-08-6(Hazardous Substances Data)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 532983-84-9 4,4'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)diphenol 
• 1174926-28-3 C₂₄H₁₆N₂O₂S 
• 1015460-23-7 C₁₉H₁₄N₂O₂S 

Relevant articles and documents

Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch

Reversibly switching the light absorption of organic molecules by redox processes is of interest for applications in sensors, light harvesting, smart materials, and medical diagnostics. This work presents a symmetrical benzothiadiazole (BTD) derivative with a high fluorescence quantum yield in solution and in the crystalline state and shows by spectroelectrochemical analysis that reversible switching of UV absorption in the neutral state, to broadband Vis/NIR absorption in the 1st oxidized state, to sharp band Vis absorption in the 2nd oxidized state, is possible. For the one-electron oxidized species, formation of a delocalized radical is confirmed by electron paramagnetic resonance spectroelectrochemistry. Furthermore, our results reveal an increasing quinoidal distortion upon the 1st and 2nd oxidation, which can be used as the leitmotif for the development of BTD based redox switches.

Visible Light-Mediated Conversion of Alcohols to Bromides by a Benzothiadiazole-Containing Organic Photocatalyst

The search for metal-free, stable and high effective photocatalysts with sufficient photo-redox potentials remains a key challenge for organic chemists. Here, we present a benzothiadiazole-containing molecular organic photocatalyst with redox potentials of ?1.30 V and +1.64 V vs. SCE. The singlet state lifetime is 13 ns. Direct conversion from aliphatic alcohols to bromides has been conducted with the designed organic photocatalyst under visible light irradiation with high efficiency and selectivity. The catalytic efficiency of the novel benzothiadiazole-based photocatalyst is comparable with the state-of-art metal and non-metal catalysts. Furthermore, advanced photophysical studies including time-resolved photoluminescence and transient absorption spectroscopy offer a powerful support for photo-induced electron transfer from photocatalyst to the reactive substrates. Lastly, no photo-bleaching effect is observed, demonstrating the high stability and recyclable of the designed organic photocatalyst. (Figure presented.).

Synthesis and self-assembly of luminescent hexacatenar molecules incorporating a 4,7-diphenyl-2,1,3-benzothiadiazole core

A new polycatenar liquid crystal containing a 4,7-diphenyl-2,1,3-benzothiadiazole core and three alkoxy chains at each end has been synthesized via a copper-catalyzed azide-alkyne click reaction and investigated by polarizing microscopy, DSC, XRD scattering, SEM, UV-vis spectroscopy and photoluminescence measurements. This compound can self-assemble into an oblique columnar liquid crystalline phase in the bulk state and form organogels in different organic solvents. It shows highly fluorescent emission with large Stokes shift in solution and has binding selectivity to Li+ among a series of cations in DMSO-CH2Cl2 solution.