17402-78-7

Basic information

• Product Name: 3-BROMO-2-NITRO-BENZO[B]THIOPHENE
• Synonyms: 3-BROMO-2-NITRO-BENZO[B]THIOPHENE;3-broMo-2-nitro-1-benzothiophene;Benzo[b]thiophene, 3-broMo-2-nitro-
• CAS NO: 17402-78-7
• Molecular Formula: C₈H₄BrNO₂S
• Molecular Weight: 258.09186
• Mol File: 17402-78-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 341.3 °C at 760 mmHg
• Flash Point: 160.2 °C
• Appearance: /
• Density: 1.829 g/cm³
• Vapor Pressure: 0.00016mmHg at 25°C
• Refractive Index: 1.737
• CAS DataBase Reference: 3-BROMO-2-NITRO-BENZO[B]THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-2-NITRO-BENZO[B]THIOPHENE(17402-78-7)
• EPA Substance Registry System: 3-BROMO-2-NITRO-BENZO[B]THIOPHENE(17402-78-7)

Safety Data

• Hazardous Substances Data: 17402-78-7(Hazardous Substances Data)

Usage

General Description

3-Bromo-2-nitro-benzo[b]thiophene is a chemical compound with the molecular formula C8H4BrNO2S. It is a heterocyclic organic compound that contains a benzene ring fused to a thiophene ring with a bromine atom and a nitro group attached to the thiophene ring. 3-BROMO-2-NITRO-BENZO[B]THIOPHENE is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It possesses potential biological activity and is frequently studied for its medicinal and chemical properties. Additionally, it is known for its photophysical properties and can be used in the development of materials for optoelectronic and sensor applications.

InChI:InChI=1/C8H4BrNO2S/c9-7-5-3-1-2-4-6(5)13-8(7)10(11)12/h1-4H

Upstream product

• 7342-82-7 3-Bromothianaphthene 
• 95-15-8 Benzo[b]thiophene 

Downstream Products

• 128554-89-2 (2-Morpholin-4-yl-ethyl)-(2-nitro-benzo[b]thiophen-3-yl)-amine 
• 172914-24-8 (2-Nitro-benzo[b]thiophen-3-yl)-p-tolyl-amine 
• 172914-28-2 (2-Nitro-benzo[b]thiophen-3-yl)-m-tolyl-amine 
• 10133-37-6 2-nitro-3-N-phenylamino-benzothiophene 
• 149338-07-8 (4-Chloro-phenyl)-(2-nitro-benzo[b]thiophen-3-yl)-amine 

Relevant articles and documents

-

-

Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons

Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%–92%), diastereoselectivity (13/1 → >20/1 dr), and enantioselectivity (75%–95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.