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804533

Sigma-Aldrich

2,2′-Bipyrazine

Synonym(s):

2,2′-Bipyrazinyl, 2,2′-Dipyrazinyl

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About This Item

Empirical Formula (Hill Notation):
C8H6N4
CAS Number:
10199-00-5
Molecular Weight:
158.16
UNSPSC Code:
12161600
NACRES:
NA.22

Assay

97%

Quality Level

100

form

powder

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst

mp

185-188 °C

InChI

1S/C8H6N4/c1-3-11-7(5-9-1)8-6-10-2-4-12-8/h1-6H

InChI key

DFXNVSIALRDJHY-UHFFFAOYSA-N

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Application

2,2′-Bipyrazine (bpz) can be used as a ligand to synthesize strongly oxidizing photocatalysts. Ruthenium-based homoleptic tris(bipyrazyl) complex [(Ru(bpz)32+] derived from 2,2′-bipyrazine ligand can be used as an effective photocatalyst for oxidatively induced organic transformations. For instance, [(Ru(bpz)32+] is capable of promoting radical cation mediated Diels–Alder cycloadditions, radical thiol-ene couplings, photooxygenation reactions, and [3+2] cycloaddition reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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An improved procedure for the preparation of Ru (bpz) 3 (PF6) 2 via a high-yielding synthesis of 2, 2?-bipyrazine
Schultz DM, et al.
Beilstein Journal of Organic Chemistry, 11(1), 61-65 (2015)
Visible Light Photocatalysis of Radical Cation Diels-Alder Cycloadditions: Preparation of Tris (2, 2?-bipyrazyl) Ruthenium (II) Bis (tetrakis (3, 5-bis (trifluoromethyl) phenyl) borate)
Lies SD, et al.
Organic Syntheses, 93, 178-199 (2003)

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