4965-26-8

Basic information

• Product Name: 5-Nitrobenzothiophene
• Synonyms: 5-NITROBENZOTHIOPHENE;5-nitrobenzo[b]thiophene;Benzo[b]thiophene, 5-nitro-
• CAS NO: 4965-26-8
• Molecular Formula: C₈H₅NO₂S
• Molecular Weight: 179.2
• Mol File: 4965-26-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 324.558°C at 760 mmHg
• Flash Point: 150.088°C
• Appearance: /
• Density: 1.435g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 5-Nitrobenzothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitrobenzothiophene(4965-26-8)
• EPA Substance Registry System: 5-Nitrobenzothiophene(4965-26-8)

Safety Data

• Hazardous Substances Data: 4965-26-8(Hazardous Substances Data)

Usage

General Description

5-Nitrobenzothiophene is a chemical compound with the molecular formula C8H5NO2S. It is a yellow solid that is soluble in organic solvents and has a melting point of 105-107°C. 5-Nitrobenzothiophene is considered a heterocyclic compound and contains a benzene ring fused to a thiophene ring with a nitro group attached to the 5-position of the thiophene ring. 5-Nitrobenzothiophene is used in the synthesis of pharmaceuticals and agrochemicals due to its potential for biological activity. It is also used as a building block in organic synthesis and as a precursor to other chemical compounds. However, 5-Nitrobenzothiophene is known to be toxic and is harmful if swallowed or inhaled, and it may cause skin and eye irritation upon contact.

InChI:InChI=1/C8H5NO2S/c10-9(11)7-1-2-8-6(5-7)3-4-12-8/h1-5H

Upstream product

• 6345-55-7 5-nitrobenzo[b]thiophene-2-carboxylic acid 
• 81146-80-7 (4-nitro-phenylsulfanyl)-acetaldehyde dimethylacetal 
• 20532-38-1 5-iodobenzo[b]thiophene 
• 81146-79-4 1-[(2,2-diethoxyethyl)sulfanyl]-4-nitrobenzene 
• 2365-48-2 Methyl thioglycolate 
• 6361-21-3 2-chloro-5-nitrobenzaldehyde 
• 20699-86-9 methyl 5-nitrobenzo[b]thiophene-2-carboxylate 
• 25785-09-5 ethyl 5-nitro-2-benzo[b]thiophenecarboxylate 
• 869624-56-6 (1E,3Z)-3-(4-methanesulfonyl-2-nitrobuta-1,3-dien-1-yl)thiophene 

Downstream Products

• 20532-28-9 5-aminobenzo[b]thiophene 
• 19492-95-6 3-bromo-5-nitrobenzo[b]thiophene 
• 1935534-79-4 3-bromo-2-chlorobenzo[b]thiophen-5-amine 
• 16957-97-4 3-bromobenzothiophene S,S-dioxide 
• 127973-90-4 N-{3-[4-(2-Chloro-benzenesulfonylaminocarbonyl)-2-methoxy-benzyl]-benzo[b]thiophen-5-yl}-2-cyclopentyl-acetamide 
• 127973-89-1 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide 
• 107786-74-3 N-[4-[5-(cyclopentyloxycarbonyl)aminobenzo[b]thien-3-ylmethyl]-3-methoxybenzoyl]benzenesulphonamide 
• 107786-72-1 methyl 4-<<5-<<(cyclopentyloxy)carbonyl>amino>benzothien-3-yl>methyl>-3-methoxybenzoate 
• 127973-87-9 methyl 4-<<5-(2-cyclopentylacetamido)benzothien-3-yl>methyl>-3-methoxybenzate 
• 107786-73-2 4-<<5-<<(cyclopentyloxy)carbonyl>amino>benzothien-3-yl>methyl>-3-methoxybenzoic acid 
• 127973-88-0 4-<<5-(2-cyclopentylacetamido)benzothien-3-yl>methyl>-3-methoxybenzoic acid 
• 107754-49-4 methyl 4-<(5-aminobenzothien-3-yl)methyl>-3-methoxybenzoate 
• 19301-35-0 benzo[b]thiophen-5-ol 
• 433303-94-7 1-(5-benzo[b]thiophenyl)piperazine 

Relevant articles and documents

Ring closure strategy leads to potent RIPK3 inhibitors

Necroptosis is a form of regulated necrotic cell death that is independent of caspases. Receptor-interacting protein kinase 3 (RIPK3) has been identified as a key regulator for necroptosis, and has been proposed as a potential therapeutic target for the treatment of diseases associated with necroptosis. In this report, we describe the design, synthesis, and evaluation of a series of novel RIPK3 inhibitors. The lead compound 38 exhibited potent activity (EC50 = 0.42 μM) in blocking TNFα, Smac mimetic and z-VAD (TSZ) induced cell death in HT-29 cells. Mechanistic studies showed that compound 38 bound to RIPK3 with high affinity (Kd = 7.1 nM), and inhibited RIPK3 kinase activity in a ADP-Glo functional assay. In addition, compound 38 displayed good selectivity over another necroptosis regulator RIPK1 (Kd = 6000 nM). Furthermore, compound 38 demonstrated excellent in vitro safety profiles with minimal inhibition of CYP isozymes and hERG potassium channel. Lastly, compound 38 efficiently blocked hypothermia and death in mice in the TNFα-induced systemic inflammatory response syndrome model.

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity

The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented,