74134-42-2

Basic information

• Product Name: 2-BROMO-6-(METHYLTHIO)PYRIDINE
• Synonyms: 2-BROMO-6-(METHYLTHIO)PYRIDINE;2-broMo-6-Methylsulphenylpyridine;2-Bromo-6-(methylsulfanyl)pyridine;2-Bromo-6-methylsulfenylpyridine;2-Methylthio-6-bromopyridine
• CAS NO: 74134-42-2
• Molecular Formula: C6H6BrNS
• Molecular Weight: 204.09
• Mol File: 74134-42-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 269.731 °C at 760 mmHg
• Flash Point: 116.93 °C
• Appearance: /
• Density: 1.617 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-BROMO-6-(METHYLTHIO)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-6-(METHYLTHIO)PYRIDINE(74134-42-2)
• EPA Substance Registry System: 2-BROMO-6-(METHYLTHIO)PYRIDINE(74134-42-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 74134-42-2(Hazardous Substances Data)

Usage

General Description

2-Bromo-6-(methylthio)pyridine is a synthetic, organic compound that belongs to the class of organohalogen compounds--specifically it is a bromopyridine with a methylthio group at position 6. It exists in a solid state and is typically a pale yellow to dark yellow or brownish color. 2-BROMO-6-(METHYLTHIO)PYRIDINE is likely to be used in the chemical industry for various applications, potentially including the production of other complex chemicals or pharmaceuticals. As with many chemicals, handling should be done with appropriate safety measures in place, as its effects on human health and the environment are not completely known or understood.

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 624-92-0 Dimethyldisulphide 
• 109-04-6 2-bromo-pyridine 
• 5188-07-8 sodium thiomethoxide 
• 75-18-3 dimethylsulfide 
• 74-93-1 methylthiol 

Relevant articles and documents

Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines

Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.

8-(BIARYL) QUINOLINE PDE4 INHIBITORS

8-(biaryl) quinolines wherein the bi-aryl group at the 8-position is in a meta relationship to the quinoline group, are PDE4 inhibitors useful in the treatment of asthma, chronic bronchitis, chronic obstructive pulmonary disease, eosinophilic granuloma, psoriasis and other benign or malignant proliferative skin diseases, endotoxic shock, laminitis in horses, colic in horses, septic shock, ulcerative colitis, Crohn's disease, reperfusion injury of the myocardium and brain, inflammatory arthritis, chronic glomerulonephritis, atopic dermatitis, urticaria, adult respiratory distress syndrome, chronic obstructive pulmonary disease in animals, diabetes insipidus, allergic rhinitis, allergic conjunctivitis, vernal conjunctivitis, arterial restenosis, ortherosclerosis, atherosclerosis, neurogenic inflammation, pain, cough, rheumatoid arthritis, ankylosing spondylitis, transplant rejection, graft versus host disease, hypersecretion of gastric acid, bacterial, fungal induced sepsis, viral induced sepsis, fungal induced septic shock, viral induced septic shock, inflammation-mediated chronic tissue degeneration, cytokine-mediated chronic tissue degeneration, osteoarthritis, cancer, cachexia, muscle wasting, depression, memory impairment, tumour growth, or cancerous invasion of normal tissues.In another aspect, the present invention is directed to a method of enhancing cognition in a healthy subject comprising administering a safe cognition enhancing amount of phosphodiesterase-4 inhibitor. In particular, this invention is directed to a method of enhancing memory, learning, retention, recall, awareness and judgement in health subjects comprising administering a safe and cognition enhancing amount of a phosphodiesterase-4 inhibitor.

LIGAND EXCHANGE AND LIGAND COUPLING VIA THE ?-SULFURANE INTERMEDIATE IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS: CONVENIENT PREPARATION OF 2,2'-BIPYRIDINES

The reaction between methyl 2-pyridyl sulfoxide (1) with Grignard reagents afforded 2,2'-bipyridine (2) in moderate yield.The reaction is considered to involve initial ligand exchange to generate 2-pyridylmagnesium halide which in the subsequent step attacks the original sulfoxide to form the ?-sulfurane that undergoes ligand coupling to afford 2.The reaction of t-butyl-2-pyridyl sulfoxide (3) with C6H5MgBr, however, gave only 2-phenylpyridine (4).This may due to steric hindrance to the initial ligand exchange.Formation of 2 is a convenient process for preparation of 2,2'-bipyridines bearing various substituents.