[15158-22-2] C₅H₁₁NO (MW 101.15)

InChI = 1S/C5H11NO/c1-3-5(2,7)4-6/h3,7H,1,4,6H2,2H3

InChIKey = HIZLKTYBQGWVMQ-UHFFFAOYSA-N

([3,3]-Sigmatropic rearrangement^1-3 and other reactions⁴)

• Physical Data: boiling point 72–75 °C (17 mmHg),¹ 75–77 °C (12 mmHg),⁴ 50–54 °C (4.5–6 mmHg).⁵ $n_{\mathrm{D}}^{24}=1.4692$.⁴
• Solubility: soluble in benzene, toluene.
• Preparative Methods: the title compound was prepared from the halogenation of isoprene using hypochlorous acid⁵ or N-bromosuccinimide under acidic conditions⁴ to give the corresponding chloro- or bromohydrin derivatives. The halohydrins were next treated with sodium or potassium hydroxide to afford 2-methyl-2-vinyloxirane. Upon reaction with aqueous ammonia (28%), the amino-allyl alcohol was obtained.^{4, 5} An alternative method involves the treatment of 1-bromo-2-methylbut-3-en-2-ol with aqueous ammonia, leading to the in situ generated 2-methyl-2-vinyloxirane, affording the title compound.¹