36901-11-8

Basic information

• Product Name: 3,6-di(pyridin-2-yl)pyridazine
• Synonyms: 3,6-di(pyridin-2-yl)pyridazine
• CAS NO: 36901-11-8
• Molecular Formula: C₁₄H₁₀N₄
• Molecular Weight: 234.256
• Mol File: 36901-11-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,6-di(pyridin-2-yl)pyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-di(pyridin-2-yl)pyridazine(36901-11-8)
• EPA Substance Registry System: 3,6-di(pyridin-2-yl)pyridazine(36901-11-8)

Safety Data

• Hazardous Substances Data: 36901-11-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 2346, 1971 DOI: 10.1021/ja00738a057

Upstream product

• 1671-87-0 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine 
• 77089-07-7 (4-(vinyloxy)phenyl)methanol 
• 766-94-9 vinyl phenyl ether 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 104942-18-9 6,13-dihydro-14-hydroxy-6,13-ethenopentacene 
• 97226-52-3 Pd((C₅NH₄)2C₄N₂H₂)Cl₂ 
• 20033-26-5 1,2,3,4-tetrachloro-9,10-dihydro-9,10-ethenoanthracene 

Downstream Products

• 119351-16-5 C₄H₂N₂(C₅H₄N)2*H⁽¹⁺⁾*SbF₆^(1-)=C₄H₂N₂(C₅H₄N)2*HSbF₆ 
• 119279-63-9 {IrH₂(3,6-bis(2'-pyridyl)pyridazine)(PPh₃)2}SbF₆ 
• 31378-26-4 tris(2,4-pentanedionato)ruthenium(III) 
• 849337-64-0 (acetylacetonate)2Ru(3,6-bis(2'-pyridyl)pyridazine) 
• 849337-67-3 [(acetylacetonate)2Ru(μ-3,6-bis(2'-pyridyl)pyridazine-H(+))Ru(acetylacetonate)2](ClO4) 
• 89484-93-5 [Ir(CO)((C₅H₄N)2C₄H₂N₂)(P(C₆H₅)3)2]⁽¹⁺⁾*PF₆^(1-) = [Ir(CO)((C₅H₄N)2C₄H₂N₂)(P(C₆H₅)3)2][PF₆] 
• 116766-92-8 {Rh(H)2(3,6-bis(2'-pyridiyl)pyridazine)(triphenylphosphine)2}PF₆*CH₂Cl₂ 
• 119279-62-8 {IrH₂(3,6-bis(2'-pyridyl)pyridazine)(PPh₃)2}PF₆ 
• 121596-39-2 {(η6-C6H6)-chloro(dppi)ruthenium(II)}PF6 

Relevant articles and documents

Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation

An azanorbornadiene bromovinyl sulfone reagent for cysteine-selective bioconjugation has been developed. Subsequent reaction with dipyridyl tetrazine leads to bond cleavage and formation of a pyrrole-linked conjugate. The latter involves ligation of the tetrazine to the azanorbornadiene-tagged protein through inverse electron demand Diels–Alder cycloaddition with subsequent double retro-Diels–Alder reactions to form a stable pyrrole linkage. The sequence of site-selective bioconjugation followed by bioorthogonal bond cleavage was efficiently employed for the labelling of three different proteins. This method benefits from easy preparation of these reagents, selectivity for cysteine, and stability after reaction with a commercial tetrazine, which has potential for the routine preparation of protein conjugates for chemical biology studies.

Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells

The cleavage of a protecting group from a protein or drug under bioorthogonal conditions enables accurate spatiotemporal control over protein or drug activity. Disclosed herein is that vinyl ethers serve as protecting groups for alcohol-containing molecules and as reagents for bioorthogonal bond-cleavage reactions. A vinyl ether moiety was installed in a range of molecules, including amino acids, a monosaccharide, a fluorophore, and an analogue of the cytotoxic drug duocarmycin. Tetrazine-mediated decaging proceeded under biocompatible conditions with good yields and reasonable kinetics. Importantly, the nontoxic, vinyl ether duocarmycin double prodrug was successfully decaged in live cells to reinstate cytotoxicity. This bioorthogonal reaction presents broad applicability and may be suitable for in vivo applications.

Thermal generation of pentacenes from soluble 6,13-dihydro-6,13- ethenopentacene precursors by a Diels-Alder-retro-Diels-Alder sequence with 3,6-disubstituted tetrazines

3,6-Substituted tetrazines 2 (a: R2 = 2-pyridyl or b: CO 2Me) react with 2,3,9,10-(R1)4-dihydro-6,13- ethenopentacene 3 in solution at elevated temperature to the corresponding pentacene 1 (a: R1 = H, b: OBn, c: F).