13958-98-0

Basic information

• Product Name: 3-Bromo-4-cyanopyridine
• Synonyms: 3-BROMOPYRIDINE-4-CARBONITRILE;3-BROMO-4-CYANOPYRIDINE;3-Bromoisonicotinonitrile;3-bromoisonicotinonitrile(SALTDATA: FREE);3-Bromo-4-cyanopyridine,95%;2-Chloro-3-fluoro-1-nitrobenzene;4-Pyridinecarbonitrile,3-bromo-
• CAS NO: 13958-98-0
• Molecular Formula: C₆H₃BrN₂
• Molecular Weight: 183.01
• Product Categories: Pyridines;Heterocycle-Pyridine series
• Mol File: 13958-98-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 92-94℃
• Boiling Point: 267.48 °C at 760 mmHg
• Flash Point: 115.568 °C
• Appearance: /
• Density: 1.726 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.48±0.18(Predicted)
• CAS DataBase Reference: 3-Bromo-4-cyanopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-4-cyanopyridine(13958-98-0)
• EPA Substance Registry System: 3-Bromo-4-cyanopyridine(13958-98-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• PackingGroup: III
• Hazardous Substances Data: 13958-98-0(Hazardous Substances Data)

Usage

Description

3-Bromo-4-cyanopyridine is an organic compound characterized by the presence of a bromine atom at the 3rd position and a cyano group at the 4th position on a pyridine ring. It is a versatile intermediate in the synthesis of various pharmaceutical compounds and has potential applications in the development of novel therapeutic agents.

Uses

Used in Pharmaceutical Synthesis:
3-Bromo-4-cyanopyridine is used as a key intermediate in the synthesis of nicotinic receptor ligands, which are crucial for addressing diseases such as nicotinic addiction, neurodegenerative disorders, and cognitive impairments. Its unique structural features enable the development of targeted therapies for these conditions.
Used in the Synthesis of Cannabinoid Receptor Agonists:
3-Bromo-4-cyanopyridine is also utilized in the synthesis of orally bioavailable cannabinoid receptor 2 (CB2) agonists. These agonists have potential applications as analgesic and anti-inflammatory agents, offering alternative treatment options for pain management and inflammation-related conditions.

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

Upstream product

• 13958-99-1 3-bromopyridine-4-carboxamide 
• 626-55-1 3-Bromopyridine 
• 7677-24-9 trimethylsilyl cyanide 
• 1610416-94-8 3-bromoisonicotinaldehyde oxime 
• 927806-21-1 (Z)-3-bromoisonicotinaldehyde oxime 
• 13959-02-9 3-bromoisonicotinic acid 
• 100-48-1 pyridine-4-carbonitrile 
• 3430-22-6 3-Bromo-4-methylpyridin 

Downstream Products

• 76006-17-2 1H-pyrazolo[3,4-c]pyridin-3-amine 
• 78790-85-9 3-amino-2-phenylthieno<2,3-c>pyridine 
• 927806-72-2 2-(2-(trifluoromethyl)phenyl)furo[2,3-c]pyridin-3-amine 
• 927804-72-6 ethyl 3-aminofuro[2,3-c]pyridine-2-carboxylate 
• 1373687-44-5 3-(2-(2-fluorophenyl)prop-1-en-1-yl)isonicotinimidamide 
• 1373687-46-7 3-(2-fluoro-5-nitrophenyl)-3-methyl-3,4-dihydro-2,6-naphthyridin-1-amine 
• 1373687-48-9 C₂₀H₂₃FN₄O₂ 
• 1373687-50-3 tert-butyl (3-(5-(5-cyanopicolinamido)-2-fluorophenyl)-3-methyl-3,4-dihydro-2,6-naphthyridin-1-yl)carbamate 
• 1373686-80-6 N-(3-(1-amino-3-methyl-3,4-dihydro-2,6-naphthyridin-3-yl)-4-fluorophenyl)-5-cyanopicolinamide 
• 1373687-42-3 3-(2-(2-fluorophenyl)prop-1-en-1-yl)isonicotinonitrile 
• 1620076-13-2 C₁₃H₇BrF₂N₂O 
• 1613436-00-2 3-(4-methylphenyl)-2,6-naphthyridin-1-one 
• 1613435-99-6 4-cyano-3-(4-methylphenylethynyl)pyridine 
• 1290059-10-7 ethyl 2-((5-bromo-4-cyano-6-(cyclohex-2-en-1-yl)-3-iodopyridin-2-yl)methyl)acrylate 

Relevant articles and documents

Efficient total syntheses of louisianins C and D

An efficient synthetic route for the preparation of louisianins C and D was developed starting with the commercially available 4-cyanopyridine. Louisianins C and D were synthesized in seven steps and with overall yields 22% and 20%, respectively, following a novel cyclization-decarboxylation sequence involving 4-bromo-6,7-dihydrocyclopenta[c]pyridin-5-one as the key intermediate.

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.

TANKYRASE INHIBITORS

The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.

NAPHTHYRIDINE DERIVATIVE

The present invention provides, for example, the following compound: wherein ring Z is pyridine or a carbocycle, each of which is substituted or unsubstituted, ring A is a carbocycle or a heterocycle, each of which is substituted or unsubstituted, R1