467-69-6

Basic information

• Product Name: 9-Hydroxy-9-fluorenecarboxylic acid
• Synonyms: FLURENOL;FLURENOL PESTANAL;9-HYDROXY-9-FLUORENECARBOXYLIC ACID;9-HYDROXYFLUOROENE-9-CARBOXYL ACID;9-Fluorenol-9-carboxylicacid;9-hydooxy-fluorene-9-carboxylicaci;9-hydroxy-9h-fluorene-9-carboxylicaci;a-Hydroxydiphenyleneaceticacid
• CAS NO: 467-69-6
• Molecular Formula: C₁₄H₁₀O₃
• Molecular Weight: 226.23
• EINECS: 207-397-1
• Product Categories: Fluorene Derivatives;Fluorenes, Flurenones;Organic acids;Fluorenes;Fluorenes & Fluorenones
• Mol File: 467-69-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 162-166 °C(lit.)
• Boiling Point: 490.5 °C at 760 mmHg
• Flash Point: 264.6 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 1.95E-10mmHg at 25°C
• BRN: 1314711
• CAS DataBase Reference: 9-Hydroxy-9-fluorenecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Hydroxy-9-fluorenecarboxylic acid(467-69-6)
• EPA Substance Registry System: 9-Hydroxy-9-fluorenecarboxylic acid(467-69-6)

Safety Data

• Hazard Codes: N,Xi
• Statements: 51/53-36/37/38
• Safety Statements: 61-36/37/39-27-26
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: LL6480000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 467-69-6(Hazardous Substances Data)

Usage

Uses

9-Hydroxy-9-fluorenecarboxylic acid was used in the synthesis of a hexameric organooxotin prismane.

Synthesis Reference(s)

The Journal of Organic Chemistry, 16, p. 279, 1951 DOI: 10.1021/jo01142a018

InChI:InChI=1/C14H10O3/c15-13(16)14(17)11-7-3-1-5-9(11)10-6-2-4-8-12(10)14/h1-8,17H,(H,15,16)/p-1

Upstream product

• 84-11-7 9,10-phenanthrenequinone 
• 56-23-5 tetrachloromethane 
• 5101-06-4 9-chloro-9H-fluorene-9-carbonyl chloride 
• 486-25-9 9-fluorenone 
• 124-38-9 carbon dioxide 
• 139022-32-5 diethyl 9H-fluorene-9,9-dicarboxylate 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 861373-58-2 9-chloro-fluorene-9-carboxylic acid fluoren-9-yl ester 
• 307329-19-7 9-acetoxy-9H-fluorene-9-carboxylic acid 
• 3002-30-0 methyl 9H-fluorene-9-carboxylate 
• 26878-12-6 ethyl fluorene-9-carboxylate 
• 1989-33-9 9H-fluorene-9-carboxylic acid 

Downstream Products

• 24539-81-9 9-hydroxy-fluorene-9-carboxylic acid-(2-diethylamino-ethyl ester) 
• 1216-44-0 methyl 9-hydroxy-9H-fluorene-9-carboxylate 
• 1989-33-9 9H-fluorene-9-carboxylic acid 
• 486-25-9 9-fluorenone 
• 343233-74-9 (4-fluoren-9-yl-phenyl)-methyl sulfide 
• 27929-89-1 2-diethylaminoethyl 9-hydroxyfluorene-9-carboxylate 
• 439117-98-3 9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide 
• 439118-01-1 1-(N-(9-hydroxy-9-fluorenylcarbonyl)azetidin-2S-yl-carbonylaminomethyl)-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzene 
• 439117-97-2 9-hydroxy-9-fluorenylcarbonyl-L-proline benzyl ester 
• 858799-33-4 9-[hydroxy-bis-(4-methoxy-phenyl)-methyl]-fluorenol-⁽⁹⁾ 
• 876498-21-4 9-(α-hydroxy-4,4'-dimethyl-benzhydryl)-fluoren-9-ol 
• 4407-88-9 9-(α-hydroxy-benzhydryl)-fluoren-9-ol 
• 33576-64-6 4-hydroxy-1-(fluorenyl-⁽⁹⁾)-benzene 
• 21846-08-2 9-(4-methoxyphenyl)-9H-fluorene 

Relevant articles and documents

Photocatalytic Carbinol Cation/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide

We have developed a new photocatalytic umpolung reaction of carbonyl compounds to generate anionic carbinol synthons. Aromatic aldehydes or ketones reacted with carbon dioxide in the presence of an iridium photocatalyst and 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzimidazole (DMBI) as a reductant under visible-light irradiation to furnish the corresponding α-hydroxycarboxylic acids through nucleophilic addition of the resulting carbinol anions to electrophilic carbon dioxide.

The epimetallation and carbonation of carbonyl and imino derivatives: Epivanadation route to 2-amino and 2-hydroxy acids

The feasibility of hydrocarboxylating carbonyl and imino derivatives by the two-step process of epimetallation and carbonation has been demonstrated with the model substrates of 9-fluorenone and 9-fluorenone anil. With lithium vanadium dihydride as the epimetallating agent, such hydrocarboxylation has led to a 75% yield of 9-hydroxy-9-fluorenecarboxylic acid and a 65% yield of 9-(N-phenylamino)-9-fluorenecarboxylic acid, respectively. Some initial success in extending the scope of this reaction to other substrates, such as benzophenone, has been achieved by using other epimetallating agents, like the presumed LiV(CH3)2 and Ti(OPri)2. A brief review of the processes and organic synthetic applications of epimetallation and transfer epimetallation of C-C π-bonds is offered as background.

Detection and characterization of a transient zwitterion, the 9-carboxylate-9-fluorenyl cation, and its conjugate acid

Laser flash photolysis of 9-hydroxy-9-fluorenecarboxylic acid in hexafluoro-2-propanol (HFIP) generates a transient with λ(max) at 495 nm that reacts with nucleophiles such as methanol and bromide and is insensitive to oxygen. In the presence of 0.15 M trifluoroacetic acid, a different transient with λ(max) at 560 nm that also reacts with nucleophiles is formed. The 495 and 560 nm species are identified as a zwitterion (the 9-carboxylate-9-fluorenyl cation) and its conjugate acid (the 9-carboxy-9-fluorenyl cation), respectively. The assignment of the zwitterion is supported by the observation of infrared absorptions in the carboxylate region that are quenched by nucleophiles with rate constants similar to those obtained by UV-visible detection. Both the zwitterion and its protonated form are observed at intermediate acid concentrations, leading to an estimate of 1 x 10-2 M-1 for the equilibrium constant for the ionization of the 9-carboxy-9-fluorenyl cation in HFIP. Absolute rate constants for reaction of the zwitterion with alcohols, anionic nucleophiles, and substituted aromatics are reported and compared to data for other 9-fluorenyl cations.