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

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

Uses

Used in Organic Synthesis:
Benzenethiol, 3,5-difluoro(9CI) is used as a key intermediate in organic synthesis for the preparation of a variety of chemical compounds. Its unique structure with fluorine substitution on the benzene ring allows for versatile chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Benzenethiol, 3,5-difluoro(9CI) serves as a building block for the development of new drug candidates. Its distinct chemical properties enable the creation of novel molecular structures with potential therapeutic applications. Researchers leverage its reactivity and structural features to design and synthesize innovative pharmaceutical agents targeting various diseases and medical conditions.
Used in Chemical Research:
Benzenethiol, 3,5-difluoro(9CI) is also utilized in chemical research to explore its properties and potential applications. Scientists investigate its reactivity, stability, and interaction with other chemical compounds to gain insights into its behavior and possible uses in various chemical processes. This research contributes to the broader understanding of fluorinated aromatic compounds and their role in chemical synthesis and material science.

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

Upstream product

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

Downstream Products

• 1050646-87-1 1-(3-bromopropylsulfanyl)-3,5-difluorobenzene 
• 1034975-06-8 5-(3,5-difluorophenylsulfanyl)-2-nitrobenzonitrile 
• 1118652-71-3 2,5-bis(3,5-difluorophenylsulfanyl)benzonitrile 
• 1001422-72-5 C₂₆H₃₁ClF₂O₄S₂ 
• 1181975-59-6 9-bromo-6-(3-((3,5-difluorophenyl)sulfanyl)propyl)-3,4,5,6-tetrahydroazepino[4,3-b]indol-1(2H)-one 
• 1181975-86-9 (3-chloropropyl)-(3,5-difluorophenyl)sulfane 
• 1100362-33-1 C₁₈H₁₃F₅O₄S 
• 1068660-64-9 3-(3,5-difluorophenylsulfanyl)-cyclohex-2-enone 
• 333783-60-1 1-[(2-bromoethyl)thio]-3,5-difluorobenzene 

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.

Novel 2-amino-4-oxo-5-arylthio-substituted-pyrrolo[2,3-d]pyrimidines as nonclassical antifolate inhibitors of thymidylate synthase

A series of 17 novel 2-amino-4-oxo-5-[(substituted phenyl)thio]pyrrolo[2,3- d]pyrimidines were synthesized as potential inhibitors of thymidylate synthase (TS) and as antitumor agents. The analogues contain a variety of electron withdrawing substituents on the phenyl ring of the side chain and were evaluated as inhibitors of human TS (hTS) and Escherichia coli TS and of human and E. coli dihydrofolate reductase (DHFR). The analogues 14, 17, and 18 were potent inhibitors of hTS with IC50 values of 0.28, 0.21, and 0.22 μM, respectively, and were more potent than the clinically used ZD1694, 2 and LY231514, 3 against human TS.

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.

An increased internal rotational barrier in thiophenol caused by meta substituents

The twofold internal barriers to rotation about the C-S bond in 3,5-diX-thiophenols were determined in solution from long-range spin-spin coupling constants.They are 3.4, 4.85, 5.3, 6.45, and 7.25 +/- 10percent kJ/mol for X = H, CH3, OCH3, F, and Cl, respectively.In 3,5-dichloro-4-hydroxythiophenol, V2 is -0.8 kJ/mol as compared to -1.9 kJ/mol in 4-methoxythiophenol.The para substituent here dominates.The observed barriers are in rough agreement with arguments based on perturbation molecular orbital theory and with MO calculations of changes in the barrier caused by substituents.The computed values appear as nearly pure twofold barriers with very small fourfold components.