2-tert-Butyl-1,1,3,3-tetramethylguanidine

2-tert-Butyl-1,1,3,3-tetramethylguanidine 2-tert-butyl-1,1,3,3-tetramethylguanidine.png 170 2-tert-butyl-1,1,3,3-tetramethylguanidine N-tert-Butyl-N,N,N,N-tetramethylguanidine BTMG, Barton's base 29166-72-1 correct FDA G5WY8E7YAG 3571581 2808676 1S/C9H21N3/c1-9(2,3)10-8(11(4)5)12(6)7/h1-7H3 YQHJFPFNGVDEDT-UHFFFAOYSA-N CC(C)(C)N=C(N(C)C)N(C)C 9 21 3 05 07 Danger 302 314 260 264 270 280 301+312 301+330+331 303+361+353 304+340 305+351+338 310 321 330 363 405 501 2-tert-Butyl-1,1,3,3-tetramethylguanidine is an organic base, also known as Barton's base. It is named after Nobel Prize-winning British chemist Derek Barton. Barton and his assistants prepared a series of guanidines with steric hindrance in 1982; in this case five alkyl groups: four methyl groups and one tert-butyl group.Barton Derek H. R. Elliott John D. Géro Stephen D. Synthesis and properties of a series of sterically hindered guanidine bases J. Chem. Soc., Perkin Trans. 1 1982 2085–2090 10.1039/P19820002085Reason and imagination : reflections on research in organic chemistry : selected papers of Derek H.R. Barton 1996 World Scientific/Imperial College Press 9810213611 In 50% water ethanol mixture, the acidity constant (pKa) of Barton's base is 14. In acetonitrile its pKa is 24.31. Synthesis The base is prepared by the reaction of tert-butylamine with a Vilsmeier salt. The latter is the reaction product of phosphorus oxychloride with tetramethylurea. Applications Barton's base can be used in many organic reactions, including in alkylations and in the formation of aziridines. It is often a milder alternative to traditional, strong inorganic bases. References Category:Guanidines Category:Non-nucleophilic bases