402718-29-0

Basic information

• Product Name: 3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER
• Synonyms: 3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER;3-CYANO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE;5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-NICOTINONITRILE;NICOTINONITRIL-5-BORONIC ACID;Nicotinonitrile-5-boronic acid pinacol ester;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 5-cyanopyridin-3-ylboronate;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-Pyridinecarbonitrile
• CAS NO: 402718-29-0
• Molecular Formula: C₁₂H₁₅BN₂O₂
• Molecular Weight: 230.07
• Product Categories: Boronic ester;Organoborons;Pyridine
• Mol File: 402718-29-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 122-124℃
• Boiling Point: 352.638ºC at 760 mmHg
• Flash Point: 167.07ºC
• Appearance: /
• Density: 1.107g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER(402718-29-0)
• EPA Substance Registry System: 3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER(402718-29-0)

Safety Data

• Hazardous Substances Data: 402718-29-0(Hazardous Substances Data)

Usage

General Description

3-Cyanopyridine-5-boronic acid pinacol ester is a boronic acid derivative that is commonly used in organic synthesis and medicinal chemistry. It is a versatile building block for the preparation of various biologically active compounds and pharmaceuticals. The pinacol ester moiety provides stability and solubility in organic solvents, making it an ideal reagent for cross-coupling reactions and other synthetic transformations. 3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER has also been investigated for its potential as a fluorescent probe for the detection of certain metal ions and as a ligand for coordination chemistry. Overall, 3-Cyanopyridine-5-boronic acid pinacol ester is an important chemical tool in the development of new molecules with potential therapeutic applications.

InChI:InChI=1/C12H15BN2O2/c1-11(2)12(3,4)17-13(16-11)10-5-9(6-14)7-15-8-10/h5,7-8H,1-4H3

Upstream product

• 35590-37-5 5-bromopyridine-3-carbonitrile 
• 73183-34-3 bis(pinacol)diborane 
• 100-54-9 pyridine-3-carbonitrile 

Downstream Products

• 1259380-34-1 5-(4-(7'-methoxy-5'H-spiro[piperidine-4,4'-pyrrolo[1,2-a]quinoxaline]-1-ylcarbonyl)phenyl)nicotinonitrile hydrochloride 
• 1260432-22-1 5-(3-(4-amino-2-(4-methoxyphenyl)-5-methyl-2H-imidazol-2-yl)phenyl)nicotinonitrile 
• 1272354-22-9 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinonitrile 
• 1272353-80-6 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinamide 
• 152803-24-2 5-hydroxypyridine-3-carbonitrile 
• 1083428-87-8 5-[6-(4-methanesulfonyl-phenyl)-2-methyl-imidazo[1,2-b]pyridazin-3-yl]-nicotinonitrile 
• 10177-11-4 5-phenylnicotinonitrile 
• 1575609-49-2 (2R,3R)-2-(2,4-difluorophenyl)-3-(2-(3-cyanopyridin-5-yl)-6,7-dihydrothiazolo[5,4-c]piperidine-5(4H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 887579-69-3 tert-butyl 5-cyanonicotinate 

Relevant articles and documents

Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation

A process for the concurrent transfer of both the NHC ligand and the difluoromethyl group from [(SIPr)Ag(CF2H)] to PdX2 (X = Cl, OAc, and OPiv) for the preparation of [(SIPr)Pd(CF2H)X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the first one-pot C-H borylation and difluoromethylation process for the preparation of difluoromethylated (hetero)arenes was developed.

Synthesis and antiprotozoal activity of dicationic m-terphenyl and 1,3-dipyridylbenzene derivatives

4,4″-Diamidino-m-terphenyl (1) and 36 analogues were prepared and assayed in vitro against Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Plasmodium falciparum, and Leishmania amazonensis. Twenty-three compounds were highly active against T. b. rhodesiense or P. falciparum. Most noteworthy were amidines 1, 10, and 11 with IC50 of 4 nM against T. b. rhodesiense, and dimethyltetrahydropyrimidinyl analogues 4 and 9 with IC50 values of ≤ 3 nM against P. falciparum. Bis-pyridylimidamide derivative 31 was 25 times more potent than benznidazole against T. cruzi and slightly more potent than amphotericin B against L. amazonensis. Terphenyldiamidine 1 and dipyridylbenzene analogues 23 and 25 each cured 4/4 mice infected with T. b. rhodesiense STIB900 with four daily 5 mg/kg intraperitoneal doses, as well as with single doses of ≤10 mg/kg. Derivatives 5 and 28 (prodrugs of 1 and 25) each cured 3/4 mice with four daily 25 mg/kg oral doses.

Pyrrolopyrimidines and Pyrrolopyridines

Compounds of formula I in free or salt or solvate form, wherein X, T1, T3 and T4 have the meanings as indicated in the specification, are useful for treating diseases mediated by the ALK-5 and/or ALK-4 receptor. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.