99389-26-1

Basic information

• Product Name: Benzenethiol, 3,5-difluoro- (9CI)
• Synonyms: Benzenethiol, 3,5-difluoro- (9CI);1,3-Difluoro-5-thiobenzene;3,5-difluoro-benzenethiol;BENZENETHIOL, 3,5-DIFLUORO-
• CAS NO: 99389-26-1
• Molecular Formula: C₆H₄F₂S
• Molecular Weight: 146.1577664
• Product Categories: HALIDE
• Mol File: 99389-26-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 155.8 °C at 760 mmHg
• Flash Point: 53 °C
• Appearance: /
• Density: 1.323 g/cm³
• Vapor Pressure: 3.83mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Benzenethiol, 3,5-difluoro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenethiol, 3,5-difluoro- (9CI)(99389-26-1)
• EPA Substance Registry System: Benzenethiol, 3,5-difluoro- (9CI)(99389-26-1)

Safety Data

• Hazardous Substances Data: 99389-26-1(Hazardous Substances Data)

Usage

General Description

Benzenethiol, 3,5-difluoro- (9CI) is a chemical compound with the molecular formula C6H4F2S. It is a derivative of benzenethiol, also known as thiophenol, in which two of the hydrogen atoms on the benzene ring are replaced by fluorine atoms. This chemical is used in organic synthesis and pharmaceutical research as a building block in the production of various compounds. It is known for its distinct aromatic odor and is considered to be toxic if ingested or inhaled in large quantities. Benzenethiol, 3,5-difluoro- (9CI) is also known to be a volatile compound and should be handled with caution in a well-ventilated environment.

InChI:InChI=1/C6H4F2S/c7-4-1-5(8)3-6(9)2-4/h1-3,9H

Upstream product

• 913091-87-9 ethyl [(3,5-difluorophenyl)sulfanyl]methanethioate 
• 372-39-4 3,5-difluoroaniline 

Downstream Products

• 1181975-57-4 6-bromo-9-(3-((3,5-difluorophenyl)sulfanyl)propyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 1620013-39-9 N-{4-[(3S)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl}-6-[2,6-difluoro-4-(methylsulfonyl)phenyl]-5-fluoropyridine-2-carboxamide 
• 1620013-40-2 4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfonyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate 
• 1355011-28-7 6-[2,6-difluoro-4-(methylsulfonyl)phenyl]-5-fluoropyridine-2-carboxylic acid 

Relevant articles and documents

PYRIDINYL AND PYRIMIDINYL SULFOXIDE AND SULFONE DERIVATIVES

Disclosed are certain pyridinyl and pyrimidinyl sulfoxide and sulfone compounds, pharmaceutical compositions comprising such compounds and methods of treatment using such compounds.

Synthesis and anti-HIV-1 activity of a series of 1-alkoxy-5-alkyl-6- (arylthio)uracils

A series of 1-alkoxy-5-alkyl-6-(arylthio)uracils was synthesized and tested for their ability to inhibit HIV-1 replication. Treatment of 2-alkyl- 3,3-bis(methylthio)acryloyl chlorides (5a-e) with AgOCN in benzene followed by reaction of the resulting isocyanates 6a-e with an appropriate alkoxyamine gave N-alkoxy-N'-((2-alkyl-3,3-bis(methylthio)acryloyl)ureas (10a-z) in good to excellent yields. Cyclization of 10a-z in AcOH containing a catalytic amount of p-TsOH produced 1-alkoxy-5-alkyl-6-(methylthio)uracils (11a-z). Oxidation of 11a-z with 3-chloroperoxybenzoic acid in CH2Cl2 resulted in high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils (12a-x and 12z) and 1-(benzyloxy)-6-(methylsulfinyl)thymine (12y), which were subsequently reacted with an appropriate arenethiol in ethanolic NaOH solution to afford 1-alkoxy-5-alkyl-6-(arylthio)uracils (14-49). Substitution at the 3- and 5- positions of the C-6-(phenylthio) ring by two methyl groups significantly increased its original anti-HIV-1 activity (EC50: 6-((3,5- dimethylphenyl)thio)-5-isopropyl-1-propoxyuracil (18), 0.064 μM; 6-((3,5- dimethylphenyl)thio)-1-(3-hydroxypropoxy)-5-isopropyluracil (23), 0.19 μM). Among the various alkoxy substituents at the N-1, the propoxy group was the most beneficial for improving the anti-HIV-1 activity. The 1-propoxy derivative 18 proved to be the most potent inhibitor of HIV-1 replication, followed by the 1-(3-hydroxypropoxy) derivative 23. Introduction of an isopropyl group at C-5 of the uracil base also remarkably enhanced the activity. When compound 18 was incubated with a rat liver homogenate preparation, no metabolite was observed, thus confirming the metabolic stability of the N-O bond in these 1-alkoxyuracils.