[7020-80-6] (E) [62058-77-9] C₆H₁₃N (MW 99.17)

InChI = 1S/C6H13N/c1-5-7-6(2,3)4/h5H,1-4H3/b7-5+

InChIKey = RPVBCVQKDPOMII-FNORWQNLSA-N

InChI = 1/C6H13N/c1-5-7-6(2,3)4/h5H,1-4H3/b7-5+

InChIKey = RPVBCVQKDPOMII-FNORWQNLBY

(acetaldehyde equivalent; synthesis of α,β-unsaturated aldehydes)

Alternate Names: N-ethylidene-1,1-dimethylethylamine; N-(ethylidene)-tert-butylamine; N-ethylidene-2-methyl-2-propaneamine.

Physical Data: bp 25–28 °C/95 mmHg; n_D^19.2 1.4005.

Solubility: sol most organic solvents.

Form Supplied in: colorless liquid; not commercially available.

Analysis of Reagent Purity: ¹H NMR; GC.

Preparative Methods: condensation of freshly distilled Acetaldehyde with t‐Butylamine without solvent.^1-4 The way the reactants are mixed is crucial. tert-Butylamine is added dropwise to 1 equiv of the aldehyde at −10 to 0 °C (eq 1). The reaction mixture is further stirred at rt for 10 min after which solid KOH is added (about 10 g per mol). After separation of the water layer, the imine is distilled over KOH using a Vigreux column. It was reported that azeotropic removal of the water, formed during the reaction, with an organic solvent, nonmixable with water, gave good results.⁵ However, it was found that this procedure with dichloromethane as solvent gave an end product which was always contaminated with the solvent.⁴

Handling, Storage, and Precautions: very sensitive to hydrolysis; store in closed vessels under an inert atmosphere in the refrigerator. Use of the freshly distilled reagent is recommended. Use in a fume hood.