| Identification | Back Directory | [Name]
4,7-dibroMobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) | [CAS]
165617-59-4 | [Synonyms]
M8498
BTT-2Br
4,8-dibromo-
4,5-c']bis[1,2,5]t
4,7-dibroMobenzo[1,2-c
4,8-dibroMobenzo-[1,2-c
4,5-c']bis[1,2,5]thiadiazole
ThBBT,4,8-di(2-thienyl)-benzo[1,2-c
4,8-Dibromobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole)
4,7-dibroMobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole)
4,8-bis(5-bromo-4-(2-hexyldecyl)thiophen-2-yl)benzo-[1,2-c
4,8-Dibromo-1H,5H-benzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole)
2λ4δ2-Benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole, 4,8-dibromo- | [Molecular Formula]
C6Br2N4S2 | [MDL Number]
MFCD24539447 | [MOL File]
165617-59-4.mol | [Molecular Weight]
352.03 |
| Chemical Properties | Back Directory | [Boiling point ]
469.3±55.0 °C(Predicted) | [density ]
3.01±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [InChI]
InChI=1S/C6Br2N4S2/c7-1-3-5(11-13-9-3)2(8)6-4(1)10-14-12-6 | [InChIKey]
JIHWVOHZFVWBMK-UHFFFAOYSA-N | [SMILES]
BrC1C2C(=NSN=2)C(Br)=C2C=1N=S=N2 |
| Hazard Information | Back Directory | [Uses]
4,7-dibroMobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole)(165617-59-4) is used as an intermediate in optoelectronic and synthetic materials.
| [Synthesis]
General procedure for the synthesis of 4,8-dibromobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) from 4,7-dibromobenzo[c][1,2,5]thiadiazole-5,6-diamine: firstly, amine compound (10 g, 30.8 mmol) obtained in step 2 was dissolved in degassed pyridine (300 ml) in an Ar atmosphere protected 1000 ml three-necked flask. Subsequently, N-thienylaniline (9.5 g, 66 mmol) and trimethylmethylsilyl chloride (39.5 g, 363.5 mmol) were added. The reaction mixture was heated to 80 °C and the reaction was stirred at this temperature overnight. After completion of the reaction, the mixture was cooled to room temperature and poured into water (200 ml). The precipitated solid was collected by filtration and washed with a solvent mixture of THF/hexane to give 6 g of crude product. Finally, purification was carried out by silica gel column chromatography (300 g of silica gel, eluent chlorobenzene/hexane, 10:3, v/v) to give 3 g of pure product in 27.6% yield. | [References]
[1] Angewandte Chemie, 1994, vol. 106, # 19, p. 2030 - 2032
[2] Tetrahedron, 1997, vol. 53, # 29, p. 10169 - 10178
[3] RSC Advances, 2014, vol. 4, # 85, p. 44902 - 44910
[4] Patent: JP2018/111679, 2018, A. Location in patent: Paragraph 0240; 0250; 0251; 0252; 0253
[5] Journal of the American Chemical Society, 2005, vol. 127, # 14, p. 5186 - 5195 |
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