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

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

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

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

Downstream Products

• 486-25-9 9-fluorenone 
• 28114-92-3 (9H-fluoren-9-yl) (phenyl) sulfane 

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).

Synthesis and conformational study of 1,1'-ethano-9,9'-bifluorenyl. Anti and Gauche conformers of a 9,9'-bifluorenyl derivative and chair and twist conformers of a dibenzo-1,5-cyclooctadiene derivative

A Hofmann-type elimination of the sulphonium salt (18) under basic conditions led to the formation of a novel o-xylylene derivative (11) which dimerized regioselectively to give the bifluorenyl/dibenzo-1,5-cyclooctadiene derivative (3). The reaction is shown to be kinetically controlled and non-concerted. The two rigid conformers (3a) and (3b) were characterised by their 1H NMR spectra and they represent respectively the first observed examples of an anti bifluorenyl derivative and a twist dibenzo-1,5-cyclooctadiene derivative. A semiempirical molecular orbital PM3 calculation supported the observed results. Dynamic 1H NMR studies indicated an interconversion process (3a) ? (3b) at higher temperatures involving a conformational barrier estimated at 65.2 kJ mol-1.

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.

Efficient Solar-Driven Hydrogen Transfer by Bismuth-Based Photocatalyst with Engineered Basic Sites

Photocatalytic organic conversions involving a hydrogen transfer (HT) step have attracted much attention, but the efficiency and selectivity under visible light irradiation still needs to be significantly enhanced. Here we have developed a noble metal-free, basic-site engineered bismuth oxybromide [Bi24O31Br10(OH)] that can accelerate the photocatalytic HT step in both reduction and oxidation reactions, i.e., nitrobenzene to azo/azoxybenzene, quinones to quinols, thiones to thiols, and alcohols to ketones under visible light irradiation and ambient conditions. Remarkably, quantum efficiencies of 42% and 32% for the nitrobenzene reduction can be reached under 410 and 450 nm irradiation, respectively. The Bi24O31Br10(OH) photocatalyst also exhibits excellent performance in up-scaling and stability under visible light and even solar irradiation, revealing economic potential for industrial applications.

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.

Tricyclic aromatic and bis-phenyl sulfinyl derivatives

The present invention provides compounds of the structure: wherein the constituent members are defined herein, including pharmaceutical compositions thereof and methods of treating diseases therewith.

Substituted thioacetamides

The present invention is directed to chemical compositions of substituted thioacetamides, processes for the preparation thereof and uses of the compositions in the treatment of diseases.

Substituted thioacetamides

The present invention is directed to chemical compositions of substituted thioacetamides, processes for the preparation thereof and uses of the compositions in the treatment of diseases.

Direct Conversion of Alcohols into Thiols

A simple one-pot reaction between alcohols and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent, LR) affords the corresponding thiols, accompanied by dehydration products, alkenes.Treatment of acyclic 1,4-diols with LR gives the 1,3-dienes. o-(Dihydroxymethyl)benzene derivatives yield the 1,3-dihydrobenzothiophenes when treated with LR.

A Novel Transformation of Alcohols to Thiols

Treatment of alcohols with 2,4-bis(p-methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulphide (Lawesson reagent) gave the corresponding thiols.