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(1,1,2,2-Tetrafluoroethyl-N,N-dimethylamine) [1550-50-1] C4H7F4N (MW 145.1) InChI = 1S/C4H7F4N/c1-9(2)4(7,8)3(5)6/h3H,1-2H3 InChIKey = VIRGYRZBWQFJGJ-UHFFFAOYSA-N (conversion of alcohols to alkyl fluorides,1 carboxylic acids to acyl fluorides,1 activated carbonyl groups to CF2,1, 2 formation of 2-difluoroacyl derivatives of cyclic 1,3-diketones,2 and 3-difluoromethyl pyrazoles3) Alternate Name: TFEDMA. Physical Data: bp 32 °C/127 mmHg, 77 °C/760 mmHg; flash point: 8–9 °C; vapor pressure: 1.48 psia at 21 °C; d 1.24 g cm−1. Solubility: soluble in carbon tetrachloride, chloroform, methylene chloride, acetonitrile, and diethyl ether. Reacts violently with water. Reacts with alcohols and THF. Form Supplied in: yellow liquid. Typical impurities: hydrolysis products: 2,2-difluoro-N,N-dimethylacetamide and HF. Analysis of Reagent Purity: 19F NMR.1 Preparative Method: prepared in >96% yield from tetrafluoroethylene (TFE) and dimethylamine.1 Purification: distillation–glass should be avoided, since TFEDMA reacts with glass at elevated temperatures. Handling, Storage, and Precautions: since TFEDMA reacts violently with water to produce HF (which can cause severe chemical burns) it has to be handled with caution, in a fume hood, by trained personnel. Due to the high reactivity of TFEDMA toward water, it is important that all substrates and solvents are dry. This material is best stored in fluoropolymer (Teflon® PTFE/Teflon® PFA) or polyethylene bottles. Glass should be avoided for storage as well as for reactions of this reagent. |
