1678-02-0

Basic information

• Product Name: 7-Phenylbenzo[b]thiophene
• Synonyms: 7-Phenylbenzo[b]thiophene
• CAS NO: 1678-02-0
• Molecular Formula: C₁₄H₁₀S
• Molecular Weight: 210.29
• Mol File: 1678-02-0.mol

Chemical Properties

• Melting Point: 35.5-36.5 °C
• Boiling Point: 148-150 °C(Press: 1.3 Torr)
• Appearance: /
• Density: 1.179±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 7-Phenylbenzo[b]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Phenylbenzo[b]thiophene(1678-02-0)
• EPA Substance Registry System: 7-Phenylbenzo[b]thiophene(1678-02-0)

Safety Data

• Hazardous Substances Data: 1678-02-0(Hazardous Substances Data)

Upstream product

• 1444457-43-5 C₁₆H₁₄O₂S 
• 318463-07-9 C₈H₄Cl₂S 
• 98-80-6 phenylboronic acid 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 1391861-09-8 C₂₀H₂₆OSSi 

Relevant articles and documents

Pd-Catalyzed Cyclization of Alkynyl Norbornene Derivatives for the Synthesis of Benzofused Heteroarenes

Modular approaches, which allow a systematic variation of heteroaromatic cores and substituents, are crucial for the development of heteroaromatic drug candidates and organic functional materials. A new strategy involving the cyclization of heteroarenes tethered with alkynes through a norbornene bridge was developed. The precursors were readily prepared by a three-component coupling process of heteroaryl halides, norbornadiene, and terminal alkynes. The Pd catalytic system derived from Pd(OAc)2 and 2-(pyrazol-1-yl)pyridine transformed a variety of five-membered heteroarenes to the corresponding benzofused products, including (di)benzothiophene, indazole, carbazole, indole, and benzofuran, with aryl and alkyl substituents at the C4(C7) position. During the cyclization process, the norbornene ring underwent a retro-Diels-Alder reaction, serving as an acetylene synthon. This approach was used to synthesize naphthalene derivatives from electron-rich arenes, demonstrating its versatility in the annulation of (hetero)aromatic rings. (Figure presented.).

Unexpected formation of 4,7-dihalobenzo[b]thiophenes using Ohira-Bestmann reagent and reactivity of the halogen-substituted benzo[b]thiophenes in Suzuki-Miyaura coupling with phenylboronic acid

Reaction of 2-(1-adamantylsulfanyl)-3,6-dihalobenzaldehydes with Ohira-Bestmann reagent gave 4,7-dihalobenzo[b]thiophenes along with normal alkyne products. Nine types of 4,7-dihalobenzo[b]thiophenes bearing chlorine, bromine, or iodine atoms, were prepared by this method. Regioselectivity in Suzuki-Miyaura cross coupling reactions of the 4,7-dihalobenzo[b]thiophenes with PhB(OH)2 was also studied.

General approach to benzo[b]thiophenes, benzo[b]furans, and dibenzofurans via gold-catalyzed cyclization of 1-heteroarylalka-2,3-dienyl acetates

An efficient and mild route to a series of benzo[b]thiophenes, benzo[b]furans, and dibenzofurans through gold-catalyzed benzannulation of 1-heteroarylalka-2,3-dienyl acetates was developed. Two possible pathways of this reaction involving gold carbene and aryl gold intermediates have been proposed on the basis of mechanistic studies.

Gold(I)-catalyzed rearrangement of 3-silyloxy-1,5-enynes: An efficient synthesis of benzo[b]thiophenes, dibenzothiophenes, dibenzofurans, and indole derivatives

With the IPr ligand (IPr=1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene) on gold(I) excellent yields in the benzanellation of 2-substituted thiophenes, benzothiophenes, pyrroles, benzofurans, and indoles were achieved. The 1-siloxybut-3-ynyl side chain