9-(4-broMobutyl)-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxaMide

9-(4-broMobutyl)-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxaMide Property

Boiling point:

531.3±50.0 °C(Predicted)

Density 

1.404±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

12.61±0.20(Predicted)

Safety

HS Code 

2924297099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

9-(4-broMobutyl)-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxaMide Chemical Properties,Usage,Production

Synthesis

General procedure: In a three-necked flask equipped with a thermometer and a dropping funnel, 9-(4-bromobutyl)-9H-fluorene-9-carboxylic acid (25.0 g, 73 mmol), dichloromethane (250 ml), oxalyl chloride (11.0 g, 87 mmol), and DMF (5 drops) were added, and the reaction was stirred for 2 hr. at room temperature and under nitrogen protection. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was dissolved in dichloromethane (50 mL). Another 2,2,2-trifluoroethylamine hydrochloride (10.9 g, 80 mmol) and triethylamine (31 ml, 220 mmol) were dissolved in dichloromethane (100 ml), and this solution was added to the dichloromethane solution of the aforementioned residue. The reaction mixture was washed sequentially with water, 1N HCl solution, saturated aqueous NaHCO3 solution and saturated brine (200 mL each, washed 3 times), the organic phase was dried with anhydrous Na2SO4 and the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: appropriate ratio of hexane/ethyl acetate) to give a light yellow oil. The oil was recrystallized from anhydrous ethanol (200 mL) at -5 °C and the solid was collected to give 9-(4-bromobutyl)-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxamide (23.7 g, 76.1% yield) as a white solid.

References

[1] Patent: CN106146385, 2016, A. Location in patent: Paragraph 0037; 0038
[2] Patent: WO2016/55934, 2016, A1. Location in patent: Paragraph 0124; 0133
[3] Patent: EP904262, 2004, B1. Location in patent: Page 145