Benzylidenecyclopropane

[7555-67-1] C10H10 (MW 130.19) InChI = 1S/C10H10/c1-2-4-9(5-3-1)8-10-6-7-10/h1-5,8H,6-7H2 InChIKey = VXAOEHNEGSMNAU-UHFFFAOYSA-N (strained cyclopropane ring capable of undergoing ring-opening reactions to give functionalized alkenes; reactive three- or two-carbon building blocks in cycloaddition reactions to carbo- and heterocycles; cyclopropane building blocks in addition reactions with ring conservation) Alternate Name: (1-phenylmethylene)cyclopropane; (cyclopropylidenemethyl)benzene. Physical Data: bp 60°C/0.3 mmHg;2 1H NMR (CDCl3) δ1.16–1.22 (m, 2H), 1.41–1.47 (m, 2H), 6.77 (t, 1H, J = 2 Hz), 7.20–7.25 (m, 1H), 7.31–7.37 (m, 2H), 7.53–7.58 (m, 2H). Solubility: soluble in most organic solvents. Form Supplied in: colorless liquid; not commercially available. Analysis of Reagent Purity: 1H NMR. Preparative Methods: one of the most popular methods is the Wittig reaction using cyclopropyltriphenylphosphonium bromide with benzaldehyde.2, 3 Purification: distillation under reduced pressure. Handling, Storage, and Precautions: the reagent is stable under normal conditions; use in a fume hood.