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9-Carboxyfluorene

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Name

9-Carboxyfluorene

EINECS 217-866-2
CAS No. 1989-33-9 Density 1.309 g/cm3
PSA 37.30000 LogP 2.88350
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 N/A 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;

Article Data 91

9-Carboxyfluorene Synthetic route

86-73-7

9H-fluorene

Dry ice (CO2)

Dry ice (CO2)

1989-33-9

9H-fluorene-9-carboxylic acid

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

9H-fluorene

124-38-9

carbon dioxide

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%
124-38-9

carbon dioxide

6630-65-5

9-chlorofluorene

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%
86-73-7

9H-fluorene

105-58-8

Diethyl carbonate

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
7509-44-6

10-diazophenanthren-9(10H)-one

A

1989-33-9

9H-fluorene-9-carboxylic acid

B

84-11-7

9,10-phenanthrenequinone

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

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

1989-33-9

9H-fluorene-9-carboxylic acid

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

Benzilic acid

A

1989-33-9

9H-fluorene-9-carboxylic acid

B

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%
86-73-7

9H-fluorene

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
76-93-7

Benzilic 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
124-38-9

carbon dioxide

1940-57-4

9H-fluoren-9-yl bromide

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-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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