19552-08-0

Basic information

• Product Name: 9H-fluorene-9-thiol
• Synonyms: 9-Mercaptofluorene;Fluorene-9-thiol;9H-fluorene-9-thiol;9-Fluorenethiol;9-Fluorenthiol;9-Mercapto-fluoren
• CAS NO: 19552-08-0
• Molecular Formula: C₁₃H₁₀S
• Molecular Weight: 198.2835
• Mol File: 19552-08-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 103-107°C
• Boiling Point: 348.5°Cat760mmHg
• Flash Point: 169°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0.000101mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 9H-fluorene-9-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-fluorene-9-thiol(19552-08-0)
• EPA Substance Registry System: 9H-fluorene-9-thiol(19552-08-0)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 19552-08-0(Hazardous Substances Data)

Usage

Description

9H-fluorene-9-thiol is an organic compound characterized by its unique structure that features a fluorene group and a thiol functional group. It is known for its ability to self-assemble onto gold surfaces and serves as a precursor for the synthesis of luminophore materials, which are essential in various applications due to their longer lifespans and more efficient luminescence.

Uses

Used in Optoelectronic Applications:
9H-fluorene-9-thiol is used as a self-assembling material for gold surfaces, which is crucial in the development of optoelectronic devices. Its ability to form stable and organized structures on gold surfaces makes it a valuable component in the fabrication of advanced optoelectronic systems.
Used in Luminescent Material Synthesis:
9H-fluorene-9-thiol is used as a precursor in the synthesis of luminophore materials, which are essential for creating light-emitting devices with longer lifespans and more efficient luminescence. These materials are vital in the development of various applications, such as organic light-emitting diodes (OLEDs), sensors, and bioimaging technologies.
Used in Surface Modification:
9H-fluorene-9-thiol is used as a surface modification agent for gold surfaces, enhancing their properties and making them suitable for various applications, such as catalysis, sensing, and drug delivery. The self-assembly of this compound onto gold surfaces allows for the creation of well-ordered and functionalized surfaces with tailored properties.

InChI:InChI=1/C13H10S/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8,13-14H

Upstream product

• 1689-64-1 9-Fluorenol 
• 1940-57-4 9H-fluoren-9-yl bromide 
• 64850-75-5 9H-fluoren-9-yl carbamimidothioate hydrobromide 
• 64850-99-3 S-(9-Fluorenyl)isothioharnstoff 
• 486-25-9 9-fluorenone 
• 830-72-8 9H-fluorene-9-thione 

Downstream Products

• 86-73-7 9H-fluorene 
• 746-47-4 tetrabenzo[5.5]fulvalene 
• 74250-07-0 α-Cinnamyl-9-fluorenylsulfid 
• 59431-17-3 9-(methylthio)fluorene 
• 486-25-9 9-fluorenone 
• 101796-83-2 difluoren-9-yl disulfide 

Relevant articles and documents

Wake promoting agents: Search for next generation modafinil, lessons learned: Part III

In searching for a next generation molecule to the novel wake promoting agent modafinil (compound 1), a series of fluorene-derived wakefulness enhancing agents were developed and evaluated in rat. Extensive pharmacokinetic studies of a potent member of the series (compound 15) revealed that the wake promotion activity of the analog was likely due to an active metabolite (compound 3).

Equilibrium Acidities of Nitroalkanes in an Ionic Liquid

The acidity ladder scale in [BMPY][NTf2] was successfully expanded toward the weak acidity region for about five more pK units compared to the previously established one. This allows the acidities of a series of 13 aliphatic and aromatic nitroalkanes to be determined accurately by the UV-vis spectroscopic method. The acidity of nitroalkane in [BMPY][NTf2] covers ～8 pK units and is significantly weaker than those in DMSO and water. The Hammett plot for 4-substituted phenylnitromethanes shows an excellent linearity with a slope of 2.06, which is rather close to that in DMSO but significantly larger than that in water (0.80). The regression analyses reveal that the solvation behavior of [BMPY][NTf2] on the acidic dissociations of C-H acids is similar to that of DMSO.

Design and synthesis of 9H-fluorenone based 1,2,3-triazole analogues as Mycobacterium tuberculosis InhA inhibitors

We prepared fifty various 9H-fluorenone based 1,2,3-triazole analogues varied with NH, –S–, and –SO2– groups using click chemistry. The target compounds were characterized by routine analytical techniques, 1H, 13CNMR, mass, elemental, single-crystal XRD (8a) and screened for in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H37Rv strain and two “wild” strains Spec. 210 and Spec. 192 and MIC50 was determined. Further, the compounds were evaluated for MTB InhA inhibition study as well. The final analogues exhibited minimum inhibitory concentration (MIC) ranging from 52.35 to >295?μm. Among the –NH– analogues, one compound 5p (MIC 58.34?μm), among –S– containing analogues four compounds 8e (MIC 66.94?μm), 8f (MIC 74.20?μm), 8g (MIC 57.55?μm), and 8q (MIC 56.11?μm), among –SO2– containing compounds one compound 10p (MIC 52.35?μm) showed less than MTB MIC 74.20?μm: Compound 4-(((9H-fluoren-9-yl)sulfonyl)methyl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole (10p) was found to be the most active compound with 73% InhA inhibition at 50?μm; it inhibited MTB with MIC 52.35?μm. Further, 10f and 10p were docked to crystal structure of InhA to know binding interaction pattern. Most active compounds were found to be non-cytotoxic against HEK 293 cell lines at 50?μm.