Chemical Properties
The o-isopropylbenzene molecule contains an aromatic ring and an alkyl substituent, and there are no strongly polar groups in the molecule, so the molecule as a whole does not have too strong a polarity. The stability of the substance is high, its substituent group structure is relatively simple, there is no particularly obvious tension, the bond energy in its molecule is relatively high, and the molecular structure is stable.
Uses
o-Cymene is an aromatic organic compound that can be synthesized from o-Toluic Acid (T536120).
Definition
ChEBI: 1-Isopropyl-2-methylbenzene is an alkylbenzene.
General Description
Intact and direct dealkylating nitration of
o-cymene with nitronium tetronium tetrafluoroborate has been reported. The kinetics of isomerization of cymene has been studied.
Synthesis
Palladium catalyst (0.005 mol, 0.01 eq.), 5.86 mg of PtBu3 (0.02 mmol, 0.04 eq.), 208 mg of potassium carbonate (1.5 mmol, 3.0 eq.), and isopropylboronic acid (65.9 mg, 0.75 mmol) were sequentially added to a dry reaction vial under air atmosphere. After 3 alternating cycles of vacuum/argon, a solution of 4-chlorotoluene (64.6 mg, 0.50 mmol) and 30 L of n-tetradecane in 1 mL of toluene was added via syringe, followed by 0.5 mL of water. The resulting homogeneous solution was stirred and reacted at 80 C for 11 hours. Upon completion of the reaction, the mixture was diluted with ether (10 mL), and the organic layer was separated and washed with water (2 x 10 mL). The combined ether organic phases were dried over anhydrous MgSO4, and the reaction mixture was filtered to remove the desiccant and the resulting filtrate was subjected to removal of volatiles at 300 mbar. The resulting residue was separated and purified by silica gel column chromatography (SiO2, pentane/diethyl ether gradient) to afford the target product o-isopropylbenzene.
