9H-Fluoren-9-ol

Base Information

• Chemical Name: 9H-Fluoren-9-ol
• CAS No.: 1689-64-1
• Molecular Formula: C13H10O
• Molecular Weight: 182.222
• Hs Code.: 29062990
• European Community (EC) Number: 216-879-0
• NSC Number: 5320
• UNII: BV0Q72R613
• DSSTox Substance ID: DTXSID4052683
• Nikkaji Number: J7.758E
• Wikipedia: Fluorenol
• Wikidata: Q5462806
• Metabolomics Workbench ID: 50693
• ChEMBL ID: CHEMBL571548
• Mol file: 1689-64-1.mol

Synonyms:9-hydroxyfluorene;fluoren-9-ol

Chemical Property of 9H-Fluoren-9-ol

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 4.76E-06mmHg at 25°C
• Melting Point: 153-154 °C(lit.)
• Refractive Index: 1.687
• Boiling Point: 367.5 °C at 760 mmHg
• PKA: 13.34±0.20(Predicted)
• Flash Point: 131.3 °C
• PSA: 20.23000
• Density: 1.253 g/cm³
• LogP: 2.74870
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 182.073164938
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

99%, ^*data from raw suppliers

9-Hydroxyfluorene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)O
• Uses: 9-Fluorenol is used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs.

Technology Process of 9H-Fluoren-9-ol

There total 150 articles about 9H-Fluoren-9-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

9-hydroxy-9-fluorene carboxylic acid (467-69-6) → 9-fluorenone (486-25-9,952573-42-1) + 9-Fluorenol (1689-64-1) + fluorenopinacol (3073-51-6)

Guidance literature:

copper(I) oxide; In acetonitrile; at 50 ℃;

DOI:10.1016/0040-4020(84)85005-X

Reference yield: 88.7%

9H-fluorene (86-73-7) → 9-fluorenone (486-25-9,952573-42-1) + 9-Fluorenol (1689-64-1)

Guidance literature:

With N-hydroxyphthalimide; oxygen; butane-2,3-dione dioxime; In acetonitrile; at 80 ℃; for 10h; under 3750.38 Torr;

DOI:10.1002/adsc.200900509

Reference yield: 68.0%

9-fluorenone (486-25-9,952573-42-1) + triphenyl germyllithium (3839-32-5) → 9-Fluorenol (1689-64-1) + triphenylgermane (2816-43-5) + hexaphenyldigermane (2816-39-9) + chlorotriphenylgermane (1626-24-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; inert atmosphere; addn. of org. compd. soln. to soln. of Ge-compd. at 0°C, mixt. keeping at 0°C for 30 min, at room temp. for 2 h, warming (40°C, 1.5 h), soln. hydrolysis (HCl); soln. extn. (ether), drying (Na2SO4), soln. concn. (reduced pressure), redissoln. (THF); (1)H-NMR;

DOI:10.1016/0022-328X(93)80008-Y

upstream raw materials:

n-butyl magnesium bromide

9-fluorenone

butyl magnesium bromide

aluminum isopropoxide

Downstream raw materials:

9H-fluorene

9-fluorenone

9-bromo-9,9'-bifluorene

spiro[9H-fluorene-9,9'(10'H)-phenanthrene]-10'-one

Refernces

Enantioselective Synthesis of Polycyclic Aromatic Hydrocarbon (PAH)-Based Planar Chiral Bent Cyclophanes by Rhodium-Catalyzed [2+2+2] Cycloaddition

10.1002/chem.202001450

The study presents the enantioselective synthesis of polycyclic aromatic hydrocarbon (PAH)-based planar chiral bent cyclophanes using rhodium-catalyzed [2+2+2] cycloaddition. The researchers achieved this by intramolecular regio- and enantioselective cycloaddition of tethered diyne benzofulvenes, followed by stepwise oxidative transformations. The synthesized planar chiral bent cyclophanes, featuring bent p-terphenyl and 9-fluorenone cores, were converted into 9-fluorenol-based cyclophanes with excellent enantiomeric excess (ee) values of over 99%. These cyclophanes exhibited high fluorescence quantum yields, significantly higher than an acyclic reference molecule, due to reduced flexibility and suppressed radiationless deactivation. The study also found that the anisotropy factors for electronic circular dichroism (ECD) increased as the tether length became shorter, enhancing the bending effect and reducing twist. The work demonstrates the utility of rhodium-catalyzed [2+2+2] cycloaddition for constructing PAH-based planar chiral bent cyclophane structures with high enantioselectivity and unique optoelectronic properties.