20577-26-8

Basic information

• Product Name: 2-BROMO-NICOTINONITRILE
• Synonyms: 2-BROMOPYRIDINE-3-CARBONITRILE;2-BROMO-NICOTINONITRILE;IFLAB-BB F1957-0002;2-bromonicotinonitrile(SALTDATA: FREE);2-broMo-3-cyanopyridin;3-Pyridinecarbonitrile,2-broMo-;2-Bromopyridine-3-carbonitrile, 2-Bromo-3-cyanopyridine;2-BroMo-nicotionitrile
• CAS NO: 20577-26-8
• Molecular Formula: C₆H₃BrN₂
• Molecular Weight: 183.01
• Product Categories: pyridine;Heterocycle-Pyridine series;cyanide| alkyl bromide
• Mol File: 20577-26-8.mol

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 296.9 °C at 760 mmHg
• Flash Point: 133.4 °C
• Appearance: /Solid
• Density: 1.72 g/cm³
• Vapor Pressure: 0.00139mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.66±0.10(Predicted)
• CAS DataBase Reference: 2-BROMO-NICOTINONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-NICOTINONITRILE(20577-26-8)
• EPA Substance Registry System: 2-BROMO-NICOTINONITRILE(20577-26-8)

Safety Data

• HazardClass: 6.1
• Hazardous Substances Data: 20577-26-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-nicotinonitrile is used as a key intermediate in the synthesis of pyridinylthiazole derivatives, which exhibit biological activity against a range of diseases and conditions. Its role in the production of these therapeutic agents highlights its importance in the development of novel pharmaceuticals.
Used in Agrochemical Industry:
2-BROMO-NICOTINONITRILE is also utilized in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals that can help improve crop yields and protect plants from pests and diseases.
Used in Material Science:
2-Bromo-nicotinonitrile plays a role in the development of new materials, where its unique chemical properties can be harnessed to create innovative products with enhanced performance characteristics.
Used in Chemical Research:
As a versatile intermediate, 2-Bromo-nicotinonitrile is employed in chemical research to explore new reactions, mechanisms, and the synthesis of complex organic molecules, further expanding the horizons of organic chemistry.

InChI:InChI=1/C6H3BrN2/c7-6-5(4-8)2-1-3-9-6/h1-3H

Upstream product

• 20577-27-9 pyrid-2-one-3-carbonitrile 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 337913-25-4 phosphorus pentaoxide 
• 20577-27-9 2-hydroxy-3-cyanopyridine 
• 14906-64-0 3-cyanopyridine N-oxide 

Downstream Products

• 86369-48-4 ethyl 2-(3-cyanopyridin-2-yl)acetate 
• 78790-83-7 amino-3 thieno<2,3-c> pyridine carboxylathe d,ethyle-2 
• 52505-46-1 ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate 
• 89407-37-4 benzyl(cyano-3 pyridyl-2) sulfure 
• 136869-49-3 3,3′-dicyano-2,2′-bipyridine 
• 854382-08-4 2-[(pyridin-4-yl)methyl]amino-3-cyanopyridine 
• 1035055-46-9 ethyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate 
• 1275609-09-0 N-[4-(1-cyanocyclopentyl)phenyl][2-[(4-pyridylmethyl)amino](3-pyridyl)]carboxamide 
• 59025-38-6 2-(pyrrolidin-1-yl)nicotinonitrile 
• 1613435-74-7 7-(4-hydroxyphenyl)-1,6-naphthyridin-5-one 
• 511240-93-0 7-(4-methylphenyl)-1,6-naphthyridin-5-one 
• 5657-54-5 7-Phenyl-5H-pyrano<4,3-b>pyridin-5-one 

Relevant articles and documents

Application of 1,1-ADEQUATE, HMBC, and Density Functional Theory to Determine Regioselectivity in the Halogenation of Pyridine N-Oxides

The 1,1-ADEQUATE spectrum clearly shows specific two-bond proton to carbon correlations to unequivocally distinguish the major and minor regioisomers of ortho-halogenated pyridines and to aid in assignment of the corresponding proton and carbon chemical shifts. M06-2X/6-31+G(d,p) free energies of the regioisomeric intermediates arising from deprotonation correctly predict the experimentally observed preference and thus can be used to tune the substituent pattern to yield a desired regiochemical outcome.

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

Highly Regioselective Halogenation of Pyridine N -Oxide: Practical Access to 2-Halo-Substituted Pyridines

A highly efficient and regioselective halogenation reaction of unsymmetrical pyridine N-oxide under mild conditions is described. The methodology provides a practical access to various 2-halo-substituted pyridines, which are pharmaceutically important intermediates.

Synthesis of gem-difluorinated 1,6-naphthyridine-5,7-diones

A synthetic route toward new 8,8-difluoro-1,6-naphthyridine-5,7-diones, which are of interest as new building blocks in pharmaceutical chemistry, is described. The key steps include a copper-mediated cross-coupling of ethyl bromodifluoroacetate and 2-bromo-3-cyanopyridine, followed by hydrolysis of the nitrile function and subsequent cyclization.

Spiro compounds

Compounds of the general formula (I): wherein Ar1represents optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V, and W each independently represent nitrogen atom or optionally substituted methine group, where at least two of them represent the said methine group; X represents methine or hydroxy substituted methine; Y represents an optionally substituted imino or oxygen atom are described and claimed. These novel spiro compounds are useful as neuropeptide Y receptor antagonists and as agents for the treatment of various kinds of cardiovascular disorders, central nervous system disorders, metabolic diseases and the like.

Spiro compounds

Spiro compounds of the general formula (I): wherein Ar1represents an optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V and W each represent a nitrogen atom or an optionally substituted methine group, wherein at least two of which represent said methine group; X represents methine; Y represents an optionally substituted imino or oxygen atom. These novel spiro compounds exhibit neuropeptide Y receptor (NPY) antagonistic activities and are useful as agents for the treatment of various diseases related to NPY, for example, cardiovascular disorders, central nervous system disorders, metobolic diseases and the like.

Novel spiro compounds

Compounds of the general formula (I): wherein Ar1 represents optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V, and W each independently represent nitrogen atom or optionally substituted methine group, where at least two of them represent the said methine group; X represents methine or hydroxy substituted methine; Y represents an optionally substituted imino or oxygen atom are described and claimed. These novel spiro compounds are useful as neuropeptide Y receptor antagonists and as agents for the treatment of various kinds of cardiovascular disorders, central nervous system disorders, metabolic diseases and the like.

Spiro compounds

Spiro compounds of the general formula (I): wherein Ar1represents an optionally substituted aryl or heteroaryl; n represents 0 or 1; T, U, V and W each represent a nitrogen atom or an optionally substituted methine group, wherein at least two of which represent said methine group; X represents nitrogen; Y represents an optionally substituted imino or oxygen atom, which exhibit neuropeptide Y receptor (NPY) antagonistic activities and are useful as agents for the treatment of various diseases related to NPY, for example, cardiovascular disorders, central nervous system disorders, metobolic diseases and the like.