5,6,7,8-Tetrafluoro-1,4-dihydro-2,9-dimethyl-1,4-ethenonaphthalene

Abstract

(5,6,7,8-Tetrafluoro-1,4-dihydro-2,9-dimethyl-1,4-ethenonaphthalene) [19128-52-0, 1164120-53-9, 1229332-66-4) C14H10F4 (MW 254.07) InChI = 1S/C14H10F4/c1-5-3-8-6(2)4-7(5)9-10(8)12(16)14(18)13(17)11(9)15/h3-4,7-8H,1-2H3 InChIKey = CIVHICMRESHFDI-UHFFFAOYSA-N (reagent used as ligand in transition metal-mediated asymmetric 1,6-addition of aryl boronates to α,β,γ,δ-unsaturated carbonyl compounds, and in polymerization of substituted acetylenes) Alternate Names: dimethyltetrafluorobenzobarrelene; tfb-Me2. Physical Data: mp 69–70 °C; bp 111 °C/0.4 mmHg. Solubility: soluble in CHCl3 and ether. Form supplied in: colorless solid. Preparative Method: tfb-Me2 can be prepared in one step by the formal [4+2] cycloaddition of p-xylene with tetrafluorobenzyne (eq 1).1 (1) Enantiomerically pure tfbs are prepared by a variant on this procedure, with resolution by preparative HPLC of a suitable intermediate, from 4-methyl anisole (eq 2).2 (2) Purification: recrystallization from EtOH. Handling, Storage, and Precautions: harmful if swallowed, very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. Store in a cool place. Keep container tightly closed in a dry and well-ventilated place. Avoid contact with skin and eyes. Avoid formation of dust and aerosols.