17347-34-1

Basic information

• Product Name: Benzo[b]thiophene-4-carbonitrile
• Synonyms: Benzo[b]thiophene-4-carbonitrile;1-benzothiophene-4-carbonitrile;4-fluorobenzothiophene
• CAS NO: 17347-34-1
• Molecular Formula: C9H5NS
• Molecular Weight: 159.2077
• Mol File: 17347-34-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 312.7±15.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Benzo[b]thiophene-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[b]thiophene-4-carbonitrile(17347-34-1)
• EPA Substance Registry System: Benzo[b]thiophene-4-carbonitrile(17347-34-1)

Safety Data

• Hazardous Substances Data: 17347-34-1(Hazardous Substances Data)

Usage

General Description

Benzo[b]thiophene-4-carbonitrile is a chemical compound with the molecular formula C9H5NS. It is a heterocyclic compound containing a benzene ring fused to a thiophene ring with a carbonitrile group attached at the 4-position. Benzo[b]thiophene-4-carbonitrile is characterized by its aromatic and heterocyclic properties, making it a useful building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. Benzo[b]thiophene-4-carbonitrile has been studied for its potential applications in drug discovery and development, particularly in the field of medicinal chemistry. Additionally, it may also have industrial uses in the production of specialty chemicals and materials.

Upstream product

• 5118-13-8 4-bromobenzo[b]thiophene 
• 77287-34-4 formamide 
• 66490-33-3 4-chlorobenzothiophene 
• 57-13-6 urea 
• 17347-32-9 6-bromobenzothiophene 
• 557-21-1 dicyanozinc 
• 195520-04-8 benzo[b]thiophen-4-yl trifluoromethanesulfonate 
• 246177-18-4 6,7-dihydrobenzo[b]thiophene-4-carbonitrile 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 88341-06-4 4-acetylbenzothiophen 
• 10133-25-2 benzo[b]thiophene-4-carboxaldehyde 
• 1119899-36-3 4-cyanobenzo[b]thiophen-2-yl-2-boronic acid 
• 1119899-37-4 7-cyanobenzo[b]thiophen-2-yl-2-boronic acid 

Relevant articles and documents

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.

Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions

The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.

PYRROLOPYRIMIDINE COMPOUNDS AND THEIR USE AS JANUS KINASE MODULATORS

Provided herein are pyrrolopyrimidine compounds of Formula (I) wherein R1 is a heteroaryl containing at least one S atom, and optionally substituted on a ring carbon by one, two, or three substituents each independently selected from the group consisting of : halo, hydroxyl, nitro, formyl, formamido, cyano, sulfonyl, carboxy, amino, amido, acylamino, carbamoyl, sulphamoyl, alkyl, alkenyl, CF3, ureido, alkynyl, alkoxy, alkanoyl, alkoxycarbonyl, carbaldehyde oxime, N -alkylsulphamoyl, N-alkylcarbamoyl, -OR13R11 or -R13R11; R2 is phenyl or pyridinyl, wherein R2 optionally substituted on a ring carbon by one, two, or three substituents each indenpendently selected from the group consisting of : halo, hydroxyl, cyano, nitro, formyl, formamido, carboxy, sulfonyl, amino, amido, -N- alkyl -amino, carbamoyl, sulphamoyl, CF3, ureido, alkyl, alkenyl, alkynyl, alkoxy, alkanoyl, alkoxycarbonyl, N-alkylsulphamoyl, N-alkylcarbamoyl, -OR11, -OR12R11, or -R12R11; and methods of making and using the same. Such compounds may be used in inflammatory or myeloproliferative disorders. The disclosure also provides for treating cancer.