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520268

Sigma-Aldrich

4,4′,4″-Tri-tert-Butyl-2,2′:6′,2″-terpyridine

95%

Synonym(s):

2,6-Bis[4-(tert-butyl)pyridin-2-yl)-4-(tert-butyl)pyridine

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About This Item

Empirical Formula (Hill Notation):
C27H35N3
CAS Number:
115091-29-7
Molecular Weight:
401.59
MDL number:
MFCD02093731
UNSPSC Code:
12352100
PubChem Substance ID:
24874100
NACRES:
NA.22

assay

95%

impurities

oligomers of tert-butyl-terpyridine

mp

215-217 °C (lit.)

SMILES string

CC(C)(C)c1ccnc(c1)-c2cc(cc(n2)-c3cc(ccn3)C(C)(C)C)C(C)(C)C

InChI

1S/C27H35N3/c1-25(2,3)18-10-12-28-21(14-18)23-16-20(27(7,8)9)17-24(30-23)22-15-19(11-13-29-22)26(4,5)6/h10-17H,1-9H3

InChI key

QMABMHJGSFUTPF-UHFFFAOYSA-N

Application

4,4′,4-Tri-tert-Butyl-2,2′:6′,2-terpyridine can be used as a ligand:      
  • In the synthesis of methylated alkanes and ketones via Ni-catalyzed methylation of unactivated alkyl halides and acid chlorides. 
  • In Ni-catalyzed reductive dimerization reaction.      
  • In allylic defluorinative reductive cross-coupling reaction in the presence of Ni as a catalyst.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000216821
0000194313
0000176328
0000176331
0000212255

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Michael R Prinsell et al.
Chemical communications (Cambridge, England), 46(31), 5743-5745 (2010-06-29)
The first general method for the reductive dimerization of alkyl halides, alkyl mesylates, alkyl trifluoroacetates, and allylic acetates is reported which proceeds with low catalyst loading (0.5 to 5 mol%), generally high yields (80% ave yield), and good functional-group tolerance.
Zhuye Liang et al.
Organic letters, 16(21), 5620-5623 (2014-10-22)
Methylation of unactivated alkyl halides and acid chlorides under Ni-catalyzed reductive coupling conditions led to efficient formation of methylated alkanes and ketones using methyl p-methyl tosylate as the methylation reagent. Moderate to excellent coupling yields as well as excellent functional
Xiao-Yu Lu et al.
Organic & biomolecular chemistry, 18(19), 3674-3678 (2020-05-08)
A nickel-catalyzed defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides has been developed. Various substituted trifluoromethyl alkenes and epoxides were found to be suitable reaction substrates. This reaction enabled C(sp3)-C(sp3) bond construction through allylic defluorinative cross-coupling of trifluoromethyl alkenes under
Gavin D Jones et al.
Journal of the American Chemical Society, 128(40), 13175-13183 (2006-10-05)
The ability of the terpyridine ligand to stabilize alkyl complexes of nickel has been central in obtaining a fundamental understanding of the key processes involved in alkyl-alkyl cross-coupling reactions. Here, mechanistic studies using isotopically labeled (TMEDA)NiMe(2) (TMEDA = N,N,N',N'-tetramethylethylenediamine) have
Cheng-Pan Zhang et al.
Journal of the American Chemical Society, 135(22), 8141-8144 (2013-05-23)
Mechanistic proposals for nickel-catalyzed coupling reactions often invoke five-coordinate alkyl- or aryl-bound Ni(II) and/or high-valent nickel(III) species, but because of their reactive nature, they have been difficult to study and fingerprint. In this work, we invoked the stabilizing properties of

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