515477
4,4′-Di-tert-butyl-2,2′-dipyridyl
98%
Synonym(s):
4,4′-Bis(tert-butyl)-2,2′-bipyridine, BBBPY
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About This Item
Empirical Formula (Hill Notation):
C18H24N2
CAS Number:
Molecular Weight:
268.40
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
98%
Quality Level
assay
98%
mp
159-161 °C (lit.)
SMILES string
CC(C)(C)c1ccnc(c1)-c2cc(ccn2)C(C)(C)C
InChI
1S/C18H24N2/c1-17(2,3)13-7-9-19-15(11-13)16-12-14(8-10-20-16)18(4,5)6/h7-12H,1-6H3
InChI key
TXNLQUKVUJITMX-UHFFFAOYSA-N
General description
4,4′-Di-tert-butyl-2,2′-dipyridyl is a bipyridyl compound that is widely employed as a ligand for transition metals in the preparation of catalysts.
Application
4,4′-Di-tert-butyl-2,2′-dipyridyl can be used as a ligand:
- In the synthesis of oxidovanadium(IV) complex [VOCl2(dbbpy)(H2O)], which is used as a catalyst for the epoxidation of cyclooctene in the presence of tert-butyl hydroperoxide.
- In iron-catalyzed ortho-allylation of 1-arylpyrazoles via C-H activation.
- In iridium-catalyzed borylation of (hetero)arenes.
- In iron-catalyzed arylation of heterocycles in the presence of metallic Mg.
- In nickel-catalyzed decarboxylation of block copolymers.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Dermal - Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Yiu-Keung Sau et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(36), 9323-9335 (2006-09-23)
Treatment of IrCl(3)x H(2)O with one equivalent of 4,4'-di-tert-butyl-2,2'-bipyridyl (dtbpy) in N,N-dimethylformamide (dmf) afforded [IrCl(3)(dmf)(dtbpy)] (1). Alkylation of 1 with Me(3)SiCH(2)MgCl resulted in C--Si cleavage of the Me(3)SiCH(2) group and formation of the Ir(III) silyl dialkyl compound [Ir(CH(2)SiMe(3))(dtbpy)(Me)(SiMe(3))] (2), which
Arimasa Matsumoto et al.
Journal of the American Chemical Society, 133(17), 6557-6559 (2011-04-09)
The [4+2] benzannulation reaction of internal or terminal alkynes with 2-biaryl, 2-heteroarylphenyl, or 2-alkenylphenyl Grignard reagents in the presence of Fe(acac)(3), 4,4'-di-tert-butyl-2,2'-bipyridyl, and 1,2-dichloro-2-methylpropane takes place at room temperature in 1 h to give 9-substituted or 9,10-disubstituted phenanthrenes and congeners
Xian Liang Ho et al.
Inorganic chemistry, 58(2), 1469-1480 (2019-01-05)
Hydrogen (H2) is a clean fuel that can potentially be a future solution for the storage of intermittent renewable energy. However, current H2 production is mainly dominated by the energy intensive steam reforming reaction, which consumes a fossil fuel, methane