119584-71-3

Basic information

• Product Name: 2-fluoro-6-(Methylthio)benzonitrile
• Synonyms: 2-fluoro-6-(Methylthio)benzonitrile
• CAS NO: 119584-71-3
• Molecular Formula: C₈H₆FNS
• Molecular Weight: 167.2033432
• Mol File: 119584-71-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-fluoro-6-(Methylthio)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-fluoro-6-(Methylthio)benzonitrile(119584-71-3)
• EPA Substance Registry System: 2-fluoro-6-(Methylthio)benzonitrile(119584-71-3)

Safety Data

• Hazardous Substances Data: 119584-71-3(Hazardous Substances Data)

Upstream product

• 74-93-1 methylthiol 
• 1897-52-5 2,6 difluorobenzonitrile 
• 138249-39-5 2-thio-6-fluorobenzonitrile 
• 74-88-4 methyl iodide 
• 5188-07-8 sodium thiomethoxide 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 1254289-43-4 C₈H₈FNOS 
• 1257075-52-7 2-(3-{2-cyano-1-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylthio)benzonitrile 
• 1257068-13-5 (+/-)-2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylsulfonyl)benzonitrile 
• 1257068-12-4 2-(3-{2-cyano-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]ethyl}pyrrolidin-1-yl)-6-(methylthio)benzonitrile 
• 254993-38-9 N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxamide 
• 254993-39-0 N-methyl-N-phenyl-1,2-dihydro-4-hydroxy-5-methylthio-1-methyl-2-oxo-quinoline-3-carboxamide 
• 675575-42-5 2-methylamino-6-thiomethylbenzonitrile 
• 119584-80-4 2,4-diamino-5-(methylthio)quinazoline 

Relevant articles and documents

Aryl methyl sulfides via SNAr using DMSO as the source of the thiomethyl moiety

A unique synthesis of aryl methyl sulfides is reported proceeding via reduction of dimethylsulfoxide to dimethylsulfide at elevated temperature in the presence of Hunig's base followed by nucleophilic aromatic substitution and demethylation. Activated aryl fluorides, chlorides, and nitrobenzenes are suitable substrates with 13 examples provided. Dimethylsulfoxide serves as a simple and inexpensive formal source of the thiomethyl moiety.

Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders: Structure-Activity Relationship

Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

Direct Synthesis of 2,4-Diaminoquinazolines from 2-Fluorobenzonitriles

In a search for new methods for preparing 2,4-diaminoquinazolines having a diversity of substituents in the benzenoid ring, it was found that the reaction of 2,6-difluorbenzonitrile with guanidine carbonate gave 2,4-diamino-5-fluoroquinazoline in excellent yield.Extension of this approach to other 2-fluorobenzonitriles, some of which were elaborated for the first time, showed that this reaction possesses considerable generality.The cyclization was sucessful even when electron donating groups were present at position six.Only in two cases where a primary or secondary amino group was also present ortho to the cyano group was this transformation unsucessful.