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165190-76-1

165190-76-1 Structure

165190-76-1 Structure
IdentificationBack Directory
[Name]

4,7-Bis(thiophen-2-yl)benzo[c][1,2,5]thiadiazole
[CAS]

165190-76-1
[Synonyms]

EA154
BT-2Th
NSC 701994
4,7-Di(2-thienyl)-2,1,3-benzothiadiazole
2,1,3-Benzothiadiazole,4,7-di-2-thienyl-
4,7-Bis(thien-2-yl)-2,1,3-benzothiadiazole
4,7-dithiophen-2-yl-2,1,3-benzothiadiazole
4,7-Di(2-thienyl)-2,1,3-benzothiadiazole>
4,7-Di(thiophene-2-yl)-2,1,3-benzothiadiazole
4,7-Bis(thiophen-2-yl)benzo[c][1,2,5]thiadiazole
2,1,3-Benzothiadiazole, 4,7-di-2-thienyl- 4,7-Bis(thien-2-yl)-2,1,3-benzothiadiazole
[EINECS(EC#)]

688-890-2
[Molecular Formula]

C14H8N2S3
[MDL Number]

MFCD18252231
[MOL File]

165190-76-1.mol
[Molecular Weight]

300.422
Chemical PropertiesBack Directory
[Melting point ]

128-129℃ (hexane )
[Boiling point ]

482.1±35.0 °C(Predicted)
[density ]

1.437±0.06 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Sealed in dry,Room Temperature
[form ]

powder to crystal
[pka]

-1.03±0.50(Predicted)
[color ]

Orange to Red
[λmax]

445nm(CHCl3)(lit.)
[InChI]

InChI=1S/C14H8N2S3/c1-3-11(17-7-1)9-5-6-10(12-4-2-8-18-12)14-13(9)15-19-16-14/h1-8H
[InChIKey]

XGERJWSXTKVPSV-UHFFFAOYSA-N
[SMILES]

N1=C2C(C3SC=CC=3)=CC=C(C3SC=CC=3)C2=NS1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2934.99.9001
Spectrum DetailBack Directory
[Spectrum Detail]

4,7-Bis(thiophen-2-yl)benzo[c][1,2,5]thiadiazole(165190-76-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-Thiopheneboronic acid

6165-68-0

4,7-DIBROMO-2,1,3-BENZOTHIADIAZOLE

15155-41-6

4,7-Bis(thiophen-2-yl)benzo[c][1,2,5]thiadiazole

165190-76-1

General procedure for the synthesis of 4,7-bis(thiophen-2-yl)benzo[c][1,2,5]thiadiazoles from 2-thiopheneboronic acid and 4,7-dibromo-2,1,3-benzothiadiazole: To a mixture of 4,7-dibromobenzo[c][1,2,5]thiadiazole (147 mg, 0.50 mmol, 1 equiv.), thiophene-2-ylboronic acid (192 mg, 1.50 mmol, 3 eq.) and K3PO4-H2O (0.90 g, 3.0 mmol, 6 eq.) was added to a mixture of THF (900 μL), followed by a THF stock solution of Pd(PAd3) (100 μL, 0.25 μmol Pd). The reaction mixture was stirred for 1 h at room temperature. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate and subsequently extracted with water. The organic layers were combined, the solvent was evaporated and the crude product was purified by fast chromatography. After drying, 143 mg (95% yield) of the target compound was obtained as an orange solid.The NMR spectral data were in agreement with literature values.

[References]

[1] Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6392 - 6395
[2] Patent: WO2017/75581, 2017, A1. Location in patent: Page/Page column 31
[3] Organic Letters, 2017, vol. 19, # 3, p. 654 - 657
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 17, p. 6111 - 6119
[5] Patent: CN106432178, 2017, A. Location in patent: Paragraph 0051; 0052; 0053; 0055
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