35590-37-5

Basic information

• Product Name: 5-Bromonicotinonitrile
• Synonyms: AKOS BBS-00003122;5-Bromonicotinonitrile,98%;3-Bromo-5-cyanopyridine 97%;5-Bromo-3-cyanopyridine,97%;3-Cyano-5-broMopyridine;5-BroMo-3-pyridinecarbonitrile;3-Bromo-5-cyanopyridine, 5-Bromopyridine-3-carbonitrile;5-Bromonicotinonitrile 97%
• CAS NO: 35590-37-5
• Molecular Formula: C₆H₃BrN₂
• Molecular Weight: 183.01
• Product Categories: blocks;Bromides;Carboxes;Pyridines;Pyridine;Organohalides;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 35590-37-5.mol

Chemical Properties

• Melting Point: 103-107 °C(lit.)
• Boiling Point: 228.8 °C at 760 mmHg
• Flash Point: 92.2 °C
• Appearance: White crystalline powder
• Density: 1.72 g/cm³
• Vapor Pressure: 0.0721mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Heated), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: -0.57±0.20(Predicted)
• CAS DataBase Reference: 5-Bromonicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromonicotinonitrile(35590-37-5)
• EPA Substance Registry System: 5-Bromonicotinonitrile(35590-37-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 35590-37-5(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

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

Upstream product

• 28733-43-9 5-bromonicotinamide 
• 144-55-8 sodium hydrogencarbonate 
• 113118-81-3 5-bromopyridine-3-carbaldehyde 
• 625-92-3 3,5-dibromopyridine 
• 2402-97-3 3-bromopyridine N-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 20826-04-4 5-bromo-3-pyridinecarboxylic acid 

Downstream Products

• 90417-31-5 ethyl-(5-cyano-3-pyridyl)carboxylate 
• 10177-11-4 5-phenylnicotinonitrile 
• 577975-32-7 5-(5-cyanopyridin-3-yl)-furan-2-carbaldehyde 
• 875414-71-4 5-(3-{[(2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]methyl}phenyl)nicotinonitrile 
• 100949-02-8 5-vinylnicotinonitrile 
• 152803-22-0 5-benzylamino-3-cyanopyridine 
• 936831-72-0 3-bromo-5-((4R)-phenyloxazolin-2-yl)pyridine 
• 497147-93-0 3-cyanopyridine-5-boronic acid 
• 370882-43-2 benzyl (1S,5S)-6-(5-cyano-pyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate 
• 799279-93-9 5-[(1S,5S)-3,6-diazabicyclo[3.2.0]heptan-3-yl]nicotinonitrile 
• 799279-93-9 5-[(1R,5R)-3,6-diazabicyclo[3.2.0]heptan-3-yl]nicotinonitrile 
• 936831-74-2 (7R)-7-methyl-4-((4R)-4-phenyl-4,5-dihydrooxazol-2-yl)-5,6-dihydro-7H-cyclopenta[c]pyridine 
• 936831-75-3 (7S)-7-methyl-4-((4R)-4-phenyl-4,5-dihydrooxazol-2-yl)-5,6-dihydro-7H-cyclopenta[c]pyridine 
• 936831-73-1 3-bromo-4-(but-3-enyl)-5-((4R)-phenyloxazolin-2-yl)pyridine 

Relevant articles and documents

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Practical one-pot conversion of aryl bromides and β-bromostyrenes into aromatic nitriles and cinnamonitriles

Various aryl bromides were efficiently converted into the corresponding aromatic nitriles in good yields by the treatment with Mg turnings and subsequently DMF, followed by treatment with molecular iodine and aq NH 3. The same treatment of aryl bromides, which are weakly reactive to Mg turnings, with iPrMgCl·LiCl and subsequently DMF, followed by the treatment with molecular iodine and aq NH3 also afforded the corresponding aromatic nitriles in good yields. On the other hand, when N-formylpiperidine was used instead of DMF, p-substituted β-bromostyrenes were converted into the corresponding p-substituted cinnamonitriles, i.e., α,β-unsaturated nitriles, in good to moderate yields by the same procedure. The reactions were carried out by means of a simple experimental procedure and did not require any toxic metal cyanides or expensive rare metals. Therefore, the present reactions are practical and environmentally benign one-pot methods for the preparation of aromatic nitriles, cinnamonitriles, and aliphatic nitriles from aryl bromides, β-bromostyrenes, and alkyl bromides, respectively, through the formation of Grignard reagents and their DMF or N-formylpiperidine adducts.

A practical and cost-efficient, one-pot conversion of aldehydes into nitriles mediated by 'activated DMSO'

Participation of activated DMSO in the one-pot transformation of aldehydes to nitriles has been described by reacting aldehydes with NHHHCl in DMSO in the absence of any added base or catalyst. The method is applicable to access a wide range of aromatic, heterocyclic, and aliphatic nitriles, in which only water is a byproduct. A straightforward and practical procedure is demonstrated on a multigram scale. Georg Thieme Verlag Stuttgart - New York.

Aluminum-catalyzed asymmetric alkylations of pyridyl-substituted alkynyl ketones with dialkylzinc reagents

Alkylations of pyridyl-substituted ynones with Et2Zn and Me 2Zn, promoted by amino acid-based chiral ligands in the presence of Al-based alkoxides, afford tertiary propargyl alcohols efficiently in 57% to >98% ee. Two easily accessib

Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)- bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors

A series of exceptionally potent agonists at neuronal nicotinic acetylcholine receptors (nAChRs) has been investigated. Several N-(3-pyridinyl) derivatives of bridged bicyclic diamines exhibit double-digit-picomolar binding affinities for the α4β2 subtype, placing them with epibatidine among the most potent nAChR ligands described to date. Structure-activity studies have revealed that substitutions, particularly hydrophilic groups in the pyridine 5-position, differentially modulate the agonist activity at ganglionic vs central nAChR subtypes, so that improved subtype selectivity can be demonstrated in vitro. Analgesic efficacy has been achieved across a broad range of pain states, including rodent models of acute thermal nociception, persistent pain, and neuropathic allodynia. Unfortunately, the hydrophilic pyridine substituents that were shown to enhance agonist selectivity for central nAChRs in vitro tend to limit CNS penetration in vivo, so that analgesic efficacy with an improved therapeutic window was not realized with those compounds.

Synthesis and structure-activity relationships of 3,8-diazabicyclo[4.2.0] octane ligands, potent nicotinic acetylcholine receptor agonists

A series of potent neuronal nicotinic acetylcholine receptor (nAChR) ligands based on a 3,8-diazabicyclo-[4.2.0]octane core have been synthesized and evaluated for affinity and agonist efficacy at the human high affinity nicotine recognition site (hα4β2) and in a rat model of persistent nociceptive pain (formalin model). Numerous analogs in this series exhibit picomolar affinity in radioligand binding assays and nanomolar agonist potency in functional assays, placing them among the most potent nAChR ligands known for the hα4β2 receptor. Several of the compounds reported in this study (i.e., 24, 25, 28, 30, 32, and 47) exhibit equivalent or greater affinity for the hα4β2 receptor relative to epibatidine, and like epibatidine, many exhibit robust analgesic efficacy in the rat formalin model of persistent pain.

6-O-carbamate-11,12-lacto-ketolide antimicrobials

6-O-Carbamate-11,12-lacto-ketolide antimicrobials of the formula: wherein R1, R2, R3 R7, and R8 are as described herein and in which the substituents have the meaning indicated in the description. These compounds are useful as antibacterial agents.

Diazabicyclic central nervous system active agents

Compounds of formula I pharmaceutical compositions of these compounds, and use of said compositions to control synaptic transmission in mammals.

Selective cyclooxygenase-2 inhibitors: Heteroaryl modified 1,2-diarylimidazoles are potent, orally active antiinflammatory agents

A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2.3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no GI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.