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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
Pricing and availability is not currently available.

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

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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. [1]

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.

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Description
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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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Certificates of Analysis (COA)

Lot/Batch Number
0000306710
0000306711
0000247556
0000247571
0000243909

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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
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
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
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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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