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

2-tert-Butyl-1,1,3,3-tetramethylguanidine
Names
Preferred IUPAC name
N′′-tert-Butyl-N,N,N′,N′-tetramethylguanidine
Other names
BTMG, Barton's base
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.697
  • InChI=1S/C9H21N3/c1-9(2,3)10-8(11(4)5)12(6)7/h1-7H3
    Key: YQHJFPFNGVDEDT-UHFFFAOYSA-N
  • CC(C)(C)N=C(N(C)C)N(C)C
Properties
C9H21N3
Molar mass 171.288 g·mol−1
Hazards
GHS labelling:
Danger
H302, H314
P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. In 50% water ethanol mixture, the acidity constant (pKa) of Barton's base is 14. In acetonitrile its pKa is 24.31.

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