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9,9-Dimethyl-9H-fluorene

9,9-Dimethyl-9H-fluorene structure

CAS No:
4569-45-3
Formula:
C15H14
Chemical Name:
9,9-Dimethyl-9H-fluorene
Synonyms:
9,9-DIMETHYLFLUORENE;9,9-Dimethyl-9H-fluo;9,9'-Dimethylfluorenee;9,9-twoMethylfluorene;9,9-dimethyl-fluororene;9,9-Dimethyl-9H-fluorene;9,9-DiMethyl-9H-fluoreneV;9,9-DiMethylfluorene,9,9-DiMethyl-9H-fluorene;9,9-Dimethylfluorene(purifiedbysublimation)
Categories:
Pharmaceutical Intermediates > Oled Material Intermediate

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9,9-Dimethyl-9H-fluorene Basic Attributes

Molecular Weight：

194.27

Exact Mass：

194.109543

EC Number：

1312995-182-4

UNII：

RFQ75I78LQ

DSSTox ID：

DTXSID40196597

HScode：

2902909090

Characteristics

PSA：

XLogP3：

4.4

Appearance：

Light yellow to white crystal powder

Density：

1.0±0.1 g/cm3

Melting Point：

96°C

Boiling Point：

287 °C

Flash Point：

138.7±10.3 °C

Refractive Index：

1.591

Safety Information

hazard class code：

20/21/22-36/37/38

safety instructions：

26-37/39

9,9-Dimethyl-9H-fluorene Use and Manufacturing

Methods of Manufacturing

Fluorene, (1 g, 6.01mmol) was placed in a Schlenk ask along with 3eqpotassium tert-butoxide (2.02 g, 18.05 mmol). The askwas purged with N2 followed by the addition of 30mL THF.The orange solution was stirred for 10min. Iodomethane(1.12mL, 18.05mmol) was added slowly to the ask over aperiod of 10min. The reaction was heated at 65C for 16hthen cooled, diluted with 100mL ice water and extractedwith DCM. The organic layer was washed with brine andsaturated sodium bicarbonate (30 mL each), dried withmagnesium sulphate, and the solvent removed in vacuo toaord yellow waxy solid (1.074g, 5.53mmol, 92%). 1H NMRspectra were in agreement with previously reported results.A mixture including 16.6 g (100.0 mmol) of fluorene, 42.5 g (300.0 mmol) of methyl iodide, 28.0 g (250.0 mmol) of KOtBu, and 600 mL of THF was stirred for 12 hours in a nitrogen atmosphere. 200 mL of water was added to the reaction mixture, and the reaction mixture was subjected to extraction twice with 500 mL ethyl acetate. The resultant organic layer was dried, filtered, concentrated, and then separated using column chromatography to obtain 16.7 g of compound 1 in light-yellow liquid form with a yield of 86%.Add 50 g of fluorene to the reaction flask then, 300 mL of THF was added, and 62.1 g of potassium t-butoxide was added thereto under ice-cooling, and after stirring for one hour, a mixture of 80.1 g of CH3I and 200 mL of THF was slowly added dropwise through a constant pressure funnel. After the dropwise addition, the reaction solution was poured into 500 ml of distilled water and stirred, and an orange solid was precipitated, suction filtered, washed with water and dried. After recrystallization from 100 ml of ethanol, The white solid Synthesis of Synthesis of 24.9 g (0.15 mol) fluorene(1), 42.0 g (0.75 mol) potassium hydroxide and 2.50 g (0.015 mol) potassium iodide were dissolved in 300 ml anhydrous dimethylsulfoxide under nitrogen atmosphere, and after the temperature of the reactants was raised to 70 C., 55.4 g (0.390 mol) iodomethane was added slowly over 4 hours with care to maintain the temperature of the reactants between 70'75 C. and stirred at 70 C. for 2 hours. Subsequently, the reactants were cooled to room temperature, 500 ml distilled water and 400 ml dichloromethane were added to extract a product, and after the extracted organic layer was washed with 400 ml distilled water twice, the recovered organic layer was dried with anhydrous magnesium sulfate and distilled under reduced pressure, and a resulting solid product was purified with 50 ml methanol twice and dried to give 22.1 g (75.9%)

Uses

Pharmaceutical intermediates are also important intermediates for the synthesis of optoelectronic materials

Computed Properties

Molecular Weight:194.27
XLogP3:4.4
Exact Mass:194.109550447
Monoisotopic Mass:194.109550447
Heavy Atom Count:15
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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