Product Name

  • Name

    9-Carboxyfluorene

  • EINECS 217-866-2
  • CAS No. 1989-33-9
  • Article Data91
  • CAS DataBase
  • Density 1.309 g/cm3
  • Solubility insoluble in water
  • Melting Point 228-231 °C(lit.)
  • Formula C14H10O2
  • Boiling Point 314.9 °C at 760 mmHg
  • Molecular Weight 210.232
  • Flash Point 158.4 °C
  • Transport Information
  • Appearance white to yellow crystalline powder
  • Safety 22-24/25-36/37/39-27-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 1989-33-9 (9-Carboxyfluorene)
  • Hazard Symbols IrritantXi
  • Synonyms Fluorene-9-carboxylicacid (6CI,7CI,8CI);9H-Fluorene-9-carboxylicacid;NSC 5322;
  • PSA 37.30000
  • LogP 2.88350

Synthetic route

9H-fluorene
86-73-7

9H-fluorene

Dry ice (CO2)

Dry ice (CO2)

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane; toluene87%
9H-fluorene
86-73-7

9H-fluorene

carbon dioxide
124-38-9

carbon dioxide

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide under 760 Torr; for 2h; Product distribution; Ambient temperature; other methylene active compounds; var. crown ethers; var. alkali carbonates; var. solvents;82%
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide under 760 Torr; for 2h; Ambient temperature;82%
With potassium carbonate; Acetanilid In dimethyl sulfoxide at 20℃; for 4h;48%
carbon dioxide
124-38-9

carbon dioxide

9-chlorofluorene
6630-65-5

9-chlorofluorene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With samarium; chloro-trimethyl-silane; tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; under 760.051 Torr; for 2h; Electrochemical reaction; Cooling with ice;81%
9H-fluorene
86-73-7

9H-fluorene

Diethyl carbonate
105-58-8

Diethyl carbonate

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; nitrogen; acetic acid In water; toluene80.7%
With hydrogenchloride; potassium ethoxide In water72.7%
Stage #1: 9H-fluorene With sodium hydride In toluene at 125℃; for 4h; Inert atmosphere; Reflux;
Stage #2: Diethyl carbonate In toluene at 90℃; for 4.5h;
Stage #3: With hydrogenchloride; water In toluene at 20 - 40℃;
10 g
Stage #1: 9H-fluorene With sodium hydride In toluene at 125℃; for 4h; Inert atmosphere;
Stage #2: Diethyl carbonate In toluene at 90℃; for 4.5h; Inert atmosphere;
Stage #3: With hydrogenchloride; acetic acid In water; toluene Reflux;
10 g
10-diazophenanthren-9(10H)-one
7509-44-6

10-diazophenanthren-9(10H)-one

A

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

B

9,10-phenanthrenequinone
84-11-7

9,10-phenanthrenequinone

Conditions
ConditionsYield
In perchloric acid Irradiation;A 80%
B 15%
In sodium hydroxide Irradiation;A 53%
B 20%
9-trimethylsilyloxy-9H-fluorene-9-carbonitrile
41380-42-1

9-trimethylsilyloxy-9H-fluorene-9-carbonitrile

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid; tin(ll) chloride Heating;74%
Benzilic acid
76-93-7

Benzilic acid

A

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

B

3,3,6,6-tetraphenyl-2,5-p-dioxanedione
467-32-3

3,3,6,6-tetraphenyl-2,5-p-dioxanedione

Conditions
ConditionsYield
With sulfuric acid In chloroform Ambient temperature;A 73%
B 11%
9H-fluorene
86-73-7

9H-fluorene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
69%
Multi-step reaction with 3 steps
1: potassium ethylate; methanol
2: acetic acid; sulfuric acid; water
3: acetic acid; aqueous hydrogen peroxide
View Scheme
Multi-step reaction with 2 steps
1: diethyl ether
View Scheme
Multi-step reaction with 2 steps
1: nBuLi
2: (i) nBuLi, THF, hexane, (ii) /BRN= 1900390/
View Scheme
Benzilic acid
76-93-7

Benzilic acid

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
trifluorormethanesulfonic acid In benzene at -45℃; for 1h;65%
With aluminium trichloride; benzene zuletzt bei Siedetemperatur;
With sulfuric acid In acetic acid
carbon dioxide
124-38-9

carbon dioxide

9H-fluoren-9-yl bromide
1940-57-4

9H-fluoren-9-yl bromide

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With bis(tricyclohexylphosphine)nickel(II) dichloride; tetra-(n-butyl)ammonium iodide; zinc In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; Schlenk technique;62%
9-fluorenone
486-25-9

9-fluorenone

carbon dioxide
124-38-9

carbon dioxide

A

9-hydroxy-9-fluorene carboxylic acid
467-69-6

9-hydroxy-9-fluorene carboxylic acid

B

9-Fluorenol
1689-64-1

9-Fluorenol

C

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With ytterbium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide under 760 Torr; for 0.833333h; Ambient temperature;A 61%
B 5%
C 15%
With ytterbium 1.) THF, HMPA, RT, 2.) RT, 1 atm, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
carbon dioxide
124-38-9

carbon dioxide

9-acetoxy-9H-fluorene
25017-68-9

9-acetoxy-9H-fluorene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With manganese; dichlorobis(trimethylphosphine)nickel In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 24h; Schlenk technique;50%
Dimethyl oxalate
553-90-2

Dimethyl oxalate

9H-fluorene
86-73-7

9H-fluorene

potassium ethoxide
917-58-8

potassium ethoxide

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With methanol Behandeln einer Loesung des Reaktionsprodukts in Essigsaeure mit wss. Schwefelsaeure bei Siedetemperatur und mit wss. Wasserstoffperoxid;
phosgene
75-44-5

phosgene

diethyl ether
60-29-7

diethyl ether

9-chlorofluorene
6630-65-5

9-chlorofluorene

methylmagnesium bromide
75-16-1

methylmagnesium bromide

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
at 0 - 5℃; anschliessende Behandlung mit festem CO2;
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

9H-fluorene
86-73-7

9H-fluorene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With diethyl ether Aufgiessen der Reaktionsloesung auf festes Kohlendioxid;
9-hydroxy-9-fluorene carboxylic acid
467-69-6

9-hydroxy-9-fluorene carboxylic acid

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With phosphorus; hydrogen iodide at 140℃; im geschlossenen Rohr;
With phosphorus; iodine; acetic acid
oxalyl dichloride
79-37-8

oxalyl dichloride

9H-fluorene
86-73-7

9H-fluorene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
at 160 - 170℃; im Rohr und nachfolgend Verseifen;
9H-fluorene
86-73-7

9H-fluorene

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With potassium amide
With sodium
With sodium
diethyl ether
60-29-7

diethyl ether

fluorenylsodium
3531-83-7

fluorenylsodium

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

9H-fluorene-9-carbonitrile
1529-40-4

9H-fluorene-9-carbonitrile

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With phosphorus; hydrogen iodide
With hydrogenchloride at 150 - 160℃; im Rohr;
fluorenylsodium
3531-83-7

fluorenylsodium

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

fluoren-9-yl-glyoxylic acid
153208-39-0

fluoren-9-yl-glyoxylic acid

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid
cumyl potassium
3003-91-6

cumyl potassium

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With diethyl ether Einleiten von Kohlendioxyd in das Reaktionsgemisch;
10-diazophenanthren-9(10H)-one
7509-44-6

10-diazophenanthren-9(10H)-one

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With 1,4-dioxane; acetic acid Irradiation;
fluoren-9-ylmagnesium bromide
91805-36-6

fluoren-9-ylmagnesium bromide

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
at 100℃;
acetic acid
64-19-7

acetic acid

10-diazophenanthren-9(10H)-one
7509-44-6

10-diazophenanthren-9(10H)-one

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
UV-Licht.Irradiation;
fluoren-9-ylidene-methanone
40012-77-9

fluoren-9-ylidene-methanone

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With water
Benzilic acid
76-93-7

Benzilic acid

benzene
71-43-2

benzene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With aluminium trichloride
Benzoylformic acid
611-73-4

Benzoylformic acid

benzene
71-43-2

benzene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
With aluminium trichloride
methanol
67-56-1

methanol

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

methyl 9H-fluorene-9-carboxylate
3002-30-0

methyl 9H-fluorene-9-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere; Sealed tube;100%
With acetyl chloride
With hydrogenchloride
ethanol
64-17-5

ethanol

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

ethyl fluorene-9-carboxylate
26878-12-6

ethyl fluorene-9-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere; Sealed tube;100%
With sulfuric acid for 8.5h; Heating;93%
With sulfuric acid
With hydrogenchloride
With hydrogenchloride
9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

9H-fluorene
86-73-7

9H-fluorene

Conditions
ConditionsYield
copper(I) oxide In acetonitrile at 50℃; for 0.25h;100%
copper(I) oxide In acetonitrile at 50℃; for 0.25h; decarboxylation of arylacetic acids in the presence of Cu2O, investigation of the effect of electronwithdrawing substituents;100%
In 1-methyl-pyrrolidin-2-one at 220℃; for 0.166667h; microwave irradiation;90%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

C18H16O2
194219-61-9

C18H16O2

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 96.6667h;92%
With lithium tert-butoxide In tetrahydrofuran at 0 - 20℃;
phenanthridine
229-87-8

phenanthridine

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

A

9H-fluorene
86-73-7

9H-fluorene

B

6-fluoren-9-yl-phenanthridine
4747-43-7

6-fluoren-9-yl-phenanthridine

C

5,6,5',6'-tetrahydro-[6,6']biphenanthridinyl
50844-93-4

5,6,5',6'-tetrahydro-[6,6']biphenanthridinyl

Conditions
ConditionsYield
In acetonitrile for 9h; Ambient temperature; Irradiation;A 90%
B 8%
C 7%
9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

A

9H-fluorene
86-73-7

9H-fluorene

B

6-fluoren-9-yl-phenanthridine
4747-43-7

6-fluoren-9-yl-phenanthridine

Conditions
ConditionsYield
With phenanthridine In acetonitrile for 9h; Ambient temperature; Irradiation;A 90%
B 8%
9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

4-Iod-1-<4-nitro-phenyl>-butan
99067-72-8

4-Iod-1-<4-nitro-phenyl>-butan

9-[3-(4-Nitrophenyl)-2-propenyl]-9-fluorenecarboxylic acid
194219-13-1

9-[3-(4-Nitrophenyl)-2-propenyl]-9-fluorenecarboxylic acid

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at 0℃; for 4.91667h;87%
propylamine
107-10-8

propylamine

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

N-propyl-9-fluorene-carboxamide
182438-56-8

N-propyl-9-fluorene-carboxamide

Conditions
ConditionsYield
Stage #1: 9H-fluorene-9-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 0.75h;
Stage #2: propylamine In dichloromethane at -40 - 20℃; for 3h;
87%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

2-(9H-fluoren-9-yl)acetonitrile
21745-43-7

2-(9H-fluoren-9-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: 9H-fluorene-9-carboxylic acid With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; iodine In chloroform at 60℃; Inert atmosphere;
Stage #2: trimethylsilyl cyanide With tetrabutyl ammonium fluoride In tetrahydrofuran; chloroform at 60℃; for 5h; Reagent/catalyst; Inert atmosphere; chemoselective reaction;
87%
9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

benzylamine
100-46-9

benzylamine

N-(phenylmethyl)-9H-fluorene-9-carboxamide

N-(phenylmethyl)-9H-fluorene-9-carboxamide

Conditions
ConditionsYield
Stage #1: 9H-fluorene-9-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 0.75h;
Stage #2: benzylamine With pyridine In dichloromethane at 0 - 20℃; for 3h;
86%
9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

ethylamine
75-04-7

ethylamine

C16H15NO
194218-93-4

C16H15NO

Conditions
ConditionsYield
Stage #1: 9H-fluorene-9-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 0.75h;
Stage #2: ethylamine In dichloromethane at 0 - 20℃; for 3h;
86%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid
182438-97-7

9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid

Conditions
ConditionsYield
Stage #1: 9H-fluorene-9-carboxylic acid With n-butyllithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: 1,4-dibromo-butane In tetrahydrofuran at 0 - 20℃; for 30.5h; Further stages.;
85%
With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 32h;85%
Stage #1: 9H-fluorene-9-carboxylic acid With n-butyllithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: 1,4-dibromo-butane In tetrahydrofuran at 0 - 20℃; for 31h;
85%
9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester
13500-53-3

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester

(2S,4R)-dibenzyl 4-(9H-fluorene-9-carbonyloxy)pyrrolidine-1,2-dicarboxylate
1256282-36-6

(2S,4R)-dibenzyl 4-(9H-fluorene-9-carbonyloxy)pyrrolidine-1,2-dicarboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;85%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

9H-fluorene-9-carboxylic acid
1989-33-9

9H-fluorene-9-carboxylic acid

9-[4-[(2-bromo-5-pyridinyl)amino]butyl]-N-propyl-9H-fluorene-9-carboxamide

9-[4-[(2-bromo-5-pyridinyl)amino]butyl]-N-propyl-9H-fluorene-9-carboxamide

Conditions
ConditionsYield
84%

9-Carboxyfluorene Specification

The IUPAC name of this chemical is 9H-fluorene-9-carboxylic acid. With the CAS registry number 1989-33-9 and EINECS 217-866-2, it is also named as 9-Carboxyfluorene. The product's categories are Fluorene Derivatives; Benzocycles; Fluorenes, Flurenones; Organic Acids; Fluorenes; Fluorenes & Fluorenones; C13 to C42+; Carbonyl Compounds; Carboxylic Acids. It is white to yellow crystalline powder which should be sealed in the container and stored in the cool and dry place. What's more, people should ensure that the workplace has well-ventilated equipment.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.87; (4)ACD/LogD (pH 7.4): -0.75; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 10.52; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.668; (14)Molar Refractivity: 59.9 cm3; (15)Molar Volume: 160.5 cm3; (16)Polarizability: 23.74×10-24 cm3; (17)Surface Tension: 58.7 dyne/cm; (18)Density: 1.309 g/cm3; (19)Flash Point: 158.4 °C; (20)Enthalpy of Vaporization: 58.71 kJ/mol; (21)Boiling Point: 314.9 °C at 760 mmHg; (22)Vapour Pressure: 0.000192 mmHg at 25°C.

Preparation of 9H-Fluorene-9-carboxylic acid: It can be obtained by fluorene and carbon dioxide. This reaction needs reagent 18-crown-6, potassium carbonate and solvent dimethylsulfoxide at ambient temperature and pressure of 760.0002. The reaction time is 2 hours. The yield is 82%.

9H-Fluorene-9-carboxylic acid can be obtained by fluorene and carbon dioxide

Uses of 9H-Fluorene-9-carboxylic acid: It is used in organic synthesis and as raw material of dyes, resins and pesticides. What's more, it can react with benzene to get fluoren-9-yl-phenyl ketone. This reaction needs catalytic agent TFSA at temperature of 63 °C. The reaction time is 4 hours. The yield is 60%.

9H-Fluorene-9-carboxylic acid can react with benzene to get fluoren-9-yl-phenyl ketone

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin, so people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After using this chemical, take off immediately all contaminated clothing. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(O)C3c1ccccc1c2c3cccc2
2. InChI:InChI=1/C14H10O2/c15-14(16)13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8,13H,(H,15,16)
3. InChIKey:DNVJGJUGFFYUPT-UHFFFAOYAY

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