1613-71-4

Basic information

• Product Name: 4-CYANO-2,2'-BIPYRIDINE
• Synonyms: 4-CYANO-2,2'-BIPYRIDINE
• CAS NO: 1613-71-4
• Molecular Formula: C₁₁H₇N₃
• Molecular Weight: 181.19
• Mol File: 1613-71-4.mol

Chemical Properties

• Melting Point: 90.0 °C
• Boiling Point: 339.6±32.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• PKA: 3.45±0.22(Predicted)
• CAS DataBase Reference: 4-CYANO-2,2'-BIPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANO-2,2'-BIPYRIDINE(1613-71-4)
• EPA Substance Registry System: 4-CYANO-2,2'-BIPYRIDINE(1613-71-4)

Safety Data

• Hazardous Substances Data: 1613-71-4(Hazardous Substances Data)

Upstream product

• 366-18-7 [2,2]bipyridinyl 
• 7677-24-9 trimethylsilyl cyanide 
• 1286763-10-7 4-cyano-2-(pyridin-2-yl)pyridine N-oxide 
• 109-04-6 2-bromo-pyridine 
• 14906-59-3 4-cyanopyridine N-oxide 
• 33252-30-1 2-chloro-4-pyridinenitrile 

Downstream Products

• 866789-68-6 1-[2,2']bipyridinyl-4-methyl-3-cyclohexyl urea 
• 482324-98-1 4-aminomethyl-2,2′-bipyridine 

Relevant articles and documents

C?H Cyanation of 6-Ring N-Containing Heteroaromatics

Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.

Synthesis of unsymmetrically substituted bipyridines by palladium-catalyzed direct C-H arylation of pyridine N -oxides

Chemical equations presented. Substituted bipyridines were efficiently prepared by direct coupling between pyridine N-oxides and halopyridines using a palladium catalyst. Pyridine N-oxides with electron-withdrawing substitutents gave the best yields. This method allows the convenient preparation of 2,2′-, 2,3′-, and 2,4′-bipyridines which are useful as functionalized ligands for metal complexes or as building blocks for supramolecular architectures.

A phase-switch purification approach for the expedient removal of tagged reagents and scavengers following their application in organic synthesis

In this paper we wish to report on a variety of expedient chemical transformations and purifications achieved via a generic 'catch and release' methodology, based on a synthetically inert bipyridyl chelating tag that can be selectively captured with a resin-bound copper(II) species. Utilising this approach we are able to derive many of the same benefits associated with both solid phase synthesis and supported reagent methods. The Royal Society of Chemistry 2005.

Rapid and efficient synthesis of functionalized bipyridines

The Negishi reaction affords a mild and efficient method to convert chloro- and bromo-pyridines into functionalized 2,2′-bi-pyridines using commercially available starting materials. This method also extends to the conversion of dibromopyridines to 5- and 6-bromobipyridines, which are powerful synthons for incorporation into larger supramolecular systems.