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515477

Sigma-Aldrich

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:
72914-19-3
Molecular Weight:
268.40
MDL number:
MFCD01863731
UNSPSC Code:
12352100
PubChem Substance ID:
24873822
NACRES:
NA.22

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

Related Categories

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral

Storage Class Code

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

Personal Protective Equipment

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
Claudina X Cammack et al.
Dalton transactions (Cambridge, England : 2003), 50(3), 858-868 (2020-12-22)
Non-aqueous redox flow batteries (RFBs) offer the possibility of higher voltage and a wider working temperature range than their aqueous counterpart. Here, we optimize the established 2.26 V Fe(bpy)3(BF4)2/Ni(bpy)3(BF4)2 asymmetric RFB to lessen capacity fade and improve energy efficiency over
Fudan Zheng et al.
International journal for parasitology. Drugs and drug resistance, 7(1), 12-22 (2016-12-30)
Nematode parasites infect ∼2 billion people world-wide. Infections are treated and prevented by anthelmintic drugs, some of which act on nicotinic acetylcholine receptors (nAChRs). There is an unmet need for novel therapeutic agents because of concerns about the development of

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