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.[1][2] In 50% water ethanol mixture, the acidity constant (pKa) of Barton's base is 14.[1] In acetonitrile its pKa is 24.31.
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.
Referencesedit
^ abBarton, Derek H. R.; Elliott, John D.; Géro, Stephen D. (1982). "Synthesis and properties of a series of sterically hindered guanidine bases". J. Chem. Soc., Perkin Trans. 1: 2085–2090. doi:10.1039/P19820002085.
^Reason and imagination : reflections on research in organic chemistry : selected papers of Derek H.R. Barton. World Scientific/Imperial College Press. 1996. ISBN9810213611.
April 18, 2024
tert, butyl, tetramethylguanidine, organic, base, also, known, barton, base, named, after, nobel, prize, winning, british, chemist, derek, barton, barton, assistants, prepared, series, guanidines, with, steric, hindrance, 1982, this, case, five, alkyl, groups,. 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 1 2 In 50 water ethanol mixture the acidity constant pKa of Barton s base is 14 1 In acetonitrile its pKa is 24 31 2 tert Butyl 1 1 3 3 tetramethylguanidine NamesPreferred IUPAC name N tert Butyl N N N N tetramethylguanidineOther names BTMG Barton s baseIdentifiersCAS Number 29166 72 13D model JSmol Interactive imageChemSpider 2808676ECHA InfoCard 100 157 697PubChem CID 3571581CompTox Dashboard EPA DTXSID10393758InChI InChI 1S C9H21N3 c1 9 2 3 10 8 11 4 5 12 6 7 h1 7H3Key YQHJFPFNGVDEDT UHFFFAOYSA NSMILES CC C C N C N C C N C CPropertiesChemical formula C 9H 21N 3Molar mass 171 288 g mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H314Precautionary statements P260 P264 P270 P280 P301 P312 P301 P330 P331 P303 P361 P353 P304 P340 P305 P351 P338 P310 P321 P330 P363 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSynthesis editThe base is prepared by the reaction of tert butylamine with a Vilsmeier salt The latter is the reaction product of phosgene with tetramethylurea Applications editBarton 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 edit a b Barton Derek H R Elliott John D Gero Stephen D 1982 Synthesis and properties of a series of sterically hindered guanidine bases J Chem Soc Perkin Trans 1 2085 2090 doi 10 1039 P19820002085 Reason and imagination reflections on research in organic chemistry selected papers of Derek H R Barton World Scientific Imperial College Press 1996 ISBN 9810213611 Retrieved from https en wikipedia org w index php title 2 tert Butyl 1 1 3 3 tetramethylguanidine amp oldid 1103859760, wikipedia, wiki, book, books, library,
