1887-60-1

Basic information

• Product Name: 5,6-DIMETHYLBENZO-2,1,3-THIADIAZOLE
• Synonyms: 5,6-DIMETHYL-2,1,3-BENZOTHIADIAZOLE;5,6-DIMETHYLBENZO-2,1,3-THIADIAZOLE;5,6-Dimethylpiazthiole
• CAS NO: 1887-60-1
• Molecular Formula: C₈H₈N₂S
• Molecular Weight: 164.23
• Mol File: 1887-60-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 89 °C
• Boiling Point: 254.6°Cat760mmHg
• Flash Point: 106.2°C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 0.0273mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: 5,6-DIMETHYLBENZO-2,1,3-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIMETHYLBENZO-2,1,3-THIADIAZOLE(1887-60-1)
• EPA Substance Registry System: 5,6-DIMETHYLBENZO-2,1,3-THIADIAZOLE(1887-60-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1887-60-1(Hazardous Substances Data)

Usage

General Description

5,6-Dimethylbenzo-2,1,3-thiadiazole is a chemical compound with the molecular formula C9H8N2S. It is a heterocyclic aromatic compound that contains a thiadiazole ring with two methyl groups attached to the benzene ring. 5,6-DIMETHYLBENZO-2,1,3-THIADIAZOLE is used in organic synthesis and material science, particularly in the development of organic semiconductors and polymers. It is known for its high thermal stability and has potential applications in electronics, optoelectronics, and photovoltaics. 5,6-Dimethylbenzo-2,1,3-thiadiazole may also have biological properties and could be investigated for its potential uses in pharmaceutical research and drug development.

InChI:InChI=1/C8H8N2S/c1-5-3-7-8(4-6(5)2)10-11-9-7/h3-4H,1-2H3

Upstream product

• 222851-56-1 N-phenylsulfinylamine 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 

Downstream Products

• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 24793-67-7 5,7-diphenyl-5H,7H-thieno[3',4':4,5]benzo[1,2-c][1,2,5]thiadiazole 6-oxide 
• 24793-65-5 C,C'-diphenyl-C,C'-benzo[1,2,5]thiadiazole-5,6-diyl-bis-methanone 
• 24793-66-6 5,7-diphenyl-5H,7H-thieno[3',4':4,5]benzo[1,2-c][1,2,5]thiadiazole 
• 24793-64-4 5,6-dibenzyl-benzo[1,2,5]thiadiazole 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 28681-49-4 4,7-dibromo-5,6-dimethylbenzo[c][1,2,5]thiadiazole 
• 106148-68-9 2-benzyl-4,5,6,7-tetramethylbenzimidazole hydrochloride 
• 106148-67-8 4,5,6,7-tetramethylbenzimidazole 
• 67130-14-7 1,2-diamino-3,4,5,6-tetramethylbenzene 

Relevant articles and documents

Functionalizing benzothiadiazole with non-conjugating ester groups as side chains in a donor-acceptor polymer improves solar cell performance

Herein, the effect of non-conjugated ester functionalization at the 5,6-position of 2,1,3-benzothiadiazole (BT) in a donor (D)-acceptor (A) conjugated polymer (CP) used for photovoltaic devices has been investigated. Positions 5 and 6 of BT were functionalized with methyl acetate groups and the structure property relationship was compared to BT with methyl groups at the 5 and 6 positions in four types of D-A CPs. Alternate co-polymers of newly synthesized methyl and methyl acetate derivatives of BT and Th-BT-Th with commonly used donors such as dithiophene (DTh) and benzodithiophene (BDT) were synthesized using Stille coupling reactions: namely, P(1,2,3,4)-Me and P(1,2,3,4)-Ac. All CPs were extensively characterized using GPC, UV-visible, 1H-NMR, 13C-NMR, TGA and CV. The optimized geometry, along with changes in the dihedral angle upon substitution with acetate groups, was analyzed by density functional theory (DFT) using B3LYP/6-31G(d,p). The side chain ester groups lower the dihedral angle, improve the optical and electrochemical properties of CPs in polymer solar cells (PSCs), improve phase separation of the active layer and performance of the fabricated PSCs compared to methyl counterparts, as investigated for P(1,2,3,4)-Me and P(1,2,3,4)-Ac. Upon fabrication of a BHJ solar cell with ITO/PEDOT:PSS/P-PC71BM/LiF/Al device geometry, CPs with methyl acetate functionalization (P2-Ac, P3-Ac and P4-Ac) resulted in higher PCEs of 1.36%, 1.17% and 0.35%, compared to their methyl counterpart CPs, P2-Me, P3-Me and P4-Me, which exhibited PCEs of 0.9%, 0.54% and 0.31%, respectively. With 1,8-diiodooctane (DIO) as an additive, a higher PCE of 1.96% was achieved for P3-Ac. Atomic force microscopy (AFM) and thin film X-ray diffraction (XRD) were used to determine the impact of side chain ester groups on π-π stacking distance among CP main chains in the film state and the morphology of the active layer of the fabricated PSCs, respectively.

Synthesis and photovoltaic properties of novel C60 bisadducts based on benzo[2,1,3]-thiadiazole

A novel C60 solar cell acceptor (BTOQC, benzo[2,1,3]-thiadiazole-o-quinodimethane-C60 bisadducts) based on benzo[2,1,3]thiadiazole has been synthesized as model to study how the thiadiazole group will affect the device performance in bulk heterojunction organic photovoltaics (BHJ-OPV) with poly(3-hexylthiophene) (P3HT) as donor. The optoelectronic, electrochemistry, and photovoltaic properties of the novel bisadduct BTOQC have been fully investigated. The best device performance of this fullerene derivative in our research was obtained as 2.50% with a high Voc of 0.74 V.

Role of cyano substituents on thiophene vinylene benzothiadiazole conjugated polymers and application as hole transporting materials in perovskite solar cells

Two narrow-band gap of donor-acceptor based conjugated polymers, BTTP and BTTP-CN were synthesized by Wittig copolymerization with thiophene or cyano-vinylene thiophene as the donor and 2,1,3-benzothiadiazole as acceptor units. The polymers were investigated by FT-IR, UV-V is, fluorescence spectroscopy, thermal stability and cyclic voltammetry (CV). The thermal analysis revealed that the BTTP polymer was stable up to 220 °C and BTTP-CN was stable up to 254 °C. The absorption spectra showed absorption maxima at 403 nm for BTTP and 397 nm for BTTP-CN. The polymers BTTP exhibited orange colour fluorescence emission at 585 nm and BTTP-CN exhibited yellow color fluorescence emission at 520 nm. The optical band gap values of undoped polymers BTTP and BTTP-CN were calculated as 2.2 and 2.13 eV respectively. Novel synthesized polymers were then enforced as dopant/additive-free hole transport materials in perovskite solar cells. Both polymers has shown the photovoltaic performance of 3.80 % for BTTP and 3.48 % for BTTP-CN under 1 sun illumination. The photovoltaic performance are compared with reference hole transporting material of spiro-OMeTAD with and without additive as 12.53 and 7.55% respectively.