100367-74-6

Basic information

• Product Name: 4-bromo-2-methylpyridine 1-oxide
• Synonyms: 4-bromo-2-methylpyridine 1-oxide
• CAS NO: 100367-74-6
• Molecular Formula: C₆H₆BrNO
• Molecular Weight: 188.03
• Mol File: 100367-74-6.mol

Chemical Properties

• Boiling Point: 178 °C(Press: 14 Torr)
• Appearance: /
• Density: 1.56±0.1 g/cm3(Predicted)
• PKA: 1.04±0.10(Predicted)
• CAS DataBase Reference: 4-bromo-2-methylpyridine 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-2-methylpyridine 1-oxide(100367-74-6)
• EPA Substance Registry System: 4-bromo-2-methylpyridine 1-oxide(100367-74-6)

Safety Data

• Hazardous Substances Data: 100367-74-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-bromo-2-methylpyridine 1-oxide is utilized as a key intermediate in organic synthesis for the preparation of various heterocyclic compounds. Its unique structure allows for the creation of a diverse range of chemical entities, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-bromo-2-methylpyridine 1-oxide is employed as a precursor for the development of new pharmaceuticals. Its potential biological activities and versatility in chemical reactions make it an attractive candidate for the synthesis of drug molecules with therapeutic applications.
Used in Medicinal Chemistry and Drug Discovery:
4-bromo-2-methylpyridine 1-oxide plays a crucial role in medicinal chemistry and drug discovery as a key intermediate in the preparation of target molecules for drug development. Its ability to be modified and incorporated into various chemical structures contributes to the advancement of novel therapeutic agents.
Used in Agrochemical Development:
4-bromo-2-methylpyridine 1-oxide also finds applications in the agrochemical sector, where it is used as a building block for the synthesis of agrochemicals with potential pesticidal or herbicidal properties. Its reactivity and structural features make it suitable for the development of effective crop protection agents.

Upstream product

• 22282-99-1 4-bromo-2-methylpyridine 
• 5470-66-6 2-methyl-4-nitropyridine N-oxide 
• 506-96-7 Acetyl bromide 
• 18437-58-6 3-methyl-4-pyridinamine 

Downstream Products

• 192642-94-7 acetic acid 4-bromopyridin-2-ylmethyl ester 
• 131747-63-2 4-bromo-2-pyridinecarboxaldehyde 
• 131747-45-0 4-bromo-2-(hydroxymethyl)pyridine 
• 192642-77-6 5-bromo-[1,2,3]triazolo[1,5-a]pyridine 
• 192642-79-8 4-bromopyridine-2-carboxaldehyde tosylhydrazone 
• 865156-50-9 1-(4-bromopyridin-2-yl)methanamine 
• 1190108-35-0 4-bromo-2-(bromomethyl)pyridine hydrobromide 

Relevant articles and documents

Human carbonic anhydrase II as host protein for the creation of artificial metalloenzymes: The asymmetric transfer hydrogenation of imines

In the presence of human carbonic anhydrase II, aryl-sulfonamide-bearing IrCp* pianostool complexes catalyze the asymmetric transfer hydrogenation of imines. Critical cofactor-protein interactions revealed by the X-ray structure of [(η5-Cp*)Ir(pico 4)Cl] 9 WT hCA II were genetically optimized to improve the catalytic performance of the artificial metalloenzyme (68% ee, kcat/KM 6.11 × 10 -3 min-1 mM-1).

Complexes of 4- and 5-bromo derivatives of 2-(hydroxymethyl)pyridine with copper(II) and cobalt(II) salts. Synthesis and X-ray crystal structures

Four copper(II) complexes (1-4) and a cobalt(II) complex (5) derived from 4-bromo-2-(hydroxymethyl)pyridine (L1) or 5-bromo-2-hydroxymethyl)pyridine (L2) with Cu(NO3)2·3H2O, CuCl2·2H2O and CoCl2·6H2O have been synthesized and their respective crystal structures studied. They show specific influences owing to the different kind of metal cations and counter anions, the hydration as well as the different position of the bromine substitution on both the coordination of the complex unit and the network structure of the crystal lattice. The Cu(II) complexes of L1 are five-coordinate [Cu(L1)2NO3]NO3·H2O (1) and [Cu(L1)2Cl]Cl·H2O (2) species with distorted quadratic pyramidal and trigonal bipyramidal coordination geometries of the N2O3 and N2O2Cl donor atoms around the Cu(II), respectively. The Cu(II) complexes of L2 are six-coordinate [Cu(L2)2(NO3)2] (3) and [Cu(L2)2Cl(H2O)]Cl·H2O (4) species with distorted octahedral coordination geometries of the N4O2 and N2O3Cl donor atoms. A distorted octahedral coordination geometry of the N2O2Cl2 donor atoms is also found in the complex unit [Co(L2)2Cl2] of the Co(II) complex 5 but showing the oxygen atoms of the chelating ligand as well as the chloride ions in a cis-position. Depending on the complex, water molecules and chloride anions are shown to act as stabilizing components of the crystal structure. The comparative structural investigation includes also known structures of the bromine-free ligand analogue 2-(hydroxymethyl)pyridine, illustrating the basic implication of the bromine substitution, mostly perceptible in the different modes of crystal packing.

ANALOGS OF 2-PRALIDOXIME AS ANTIDOTES AGAINST ORGANOPHOSPHORUS NERVE AGENTS

Provided herein are compounds useful in treating exposure to an organophosphorus compound, such as a nerve agent, pesticide, or, generally, an acetylcholinesterase inhibitor, such as sarin. Compositions, e.g. pharmaceutical compositions or dosage forms, comprising the compounds also are provided herein. Methods of treating a patient exposed to a nerve agent, pesticide, or, generally, an acetylcholinesterase inhibitor, e.g., an organophosphorus compound, such as sarin, also are provided.

Metal- and base-free regioselective thiolation of the methyl C(sp3)-H bond in 2-picoline: N -oxides

A one-pot, two-step synthesis of pyridine-2-ylmethyl thioethers is developed through a TFAA-mediated [3,3]-sigmatropic rearrangement of pyridine N-oxides and TBAB-catalyzed direct conversion of trifluoroacetates into thioethers under metal- and base-free conditions. This methodology enables thiolation of the unactivated methyl C(sp3)-H bond in 2-picolines with thiols. Remarkable features of the method include high regioselectivity, step- and atom-economy, mild conditions, simple operation, wide substrate scope and scalability. Furthermore, the method has been successfully applied to the synthesis of omeprazole sulfide and rabeprazole sulfide without the need for TBAB catalysis. A comprehensive green chemistry metrics analysis indicated that this method is much more efficient and greener than the reported synthesis of rabeprazole sulfide.

MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF

Provided are novel compounds of Formula (I): and pharmaceutically acceptable salts thereof, which are useful for treating a variety of diseases, disorders or conditions, associated with methyl modifying enzymes. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I), pharmaceutically acceptable salts thereof, and methods for their use in treating one or more diseases, disorders or conditions, associated with methyl modifying enzymes.

BENZENESULFONAMIDES USEFUL AS SODIUM CHANNEL INHIBITORS

The invention relates to sulfonamide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to a new sulfonamide Nav1.7 inhibitors of formula (I), or a pharmaceutically acceptable salt thereof, wherein X, R1, R2, R3a, R3b and R4 are as defined in the description. Nav 1.7 inhibitors are potentially useful in the treatment of a wide range of disorders, particularly pain.

Anchoring a molecular iron catalyst to solar-responsive WO3 improves the rate and selectivity of photoelectrochemical water oxidation

Molecular catalysts help overcome the kinetic limitations of water oxidation and generally result in faster rates for water oxidation than do heterogeneous catalysts. However, molecular catalysts typically function in the dark and therefore require sacrificial oxidants such as Ce4+ or S2O82- to provide the driving force for the reaction. In this Communication, covalently anchoring a phosphonate-derivatized complex, Fe(tebppmcn)Cl2 (1), to WO3 removes the need for a sacrificial oxidant and increases the rate of photoelectrochemical water oxidation on WO3 by 60%. The dual-action catalyst, 1-WO3, also gives rise to increased selectivity for water oxidation in pH 3 Na 2SO4 (56% on bare WO3, 79% on 1-WO 3). This approach provides promising alternative routes for solar water oxidation.

Inhibition of 1-deoxy-d-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies

1-Deoxy-d-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.

Supported palladium catalysis using a heteroleptic 2-methylthiomethylpyridine-N,S-donor motif for Mizoroki-Heck and Suzuki-Miyaura coupling, including continuous organic monolith in capillary microscale flow-through mode

Flow-through catalysis utilising (2-methylthiomethylpyridine)palladium(II) chloride species covalently attached to a macroporous continuous organic polymer monolith synthesised within fused silica capillaries of internal diameter 250 μm is described, together with related studies of ground bulk monolith compared with supported catalysis on Merrifield and Wang beads and homogeneous catalysis under identical conditions to bulk supported catalysis. The monolith substrate, poly(chloromethylstyrene-co-divinylbenzene), has a backbone directly related to Merrifield and Wang resins. The homogeneous precatalyst PdCl2(L2) (L2=4-(4-benzyloxyphenyl)-2-methylthiomethylpyridine) contains the benzyloxyphenyl group on its periphery as a model for the spacer between the 'PdCl2(N～S)' centre and the polymer substituent of the resins and monolith. Suzuki-Miyaura and Mizoroki-Heck catalysis exhibit anticipated trends in reactivity with variation of aryl halide reagents for each system, and show that supported catalysis on beads and monolith gives higher yields than for homogeneous catalysis. The synthesis of 2-methylthiomethylpyridines is presented, together with crystal structures of 4-bromo-2-bromomethylpyridine hydrobromide, 4-(4-hydroxyphenyl)-2-methylthiomethylpyridine (L1), PdCl2(L1) and PdCl2(L2). Hydrogen bonding occurs in 4-bromo-2-bromomethylpyridine hydrobromide as N-H?Br interactions, in 4-(4-hydroxyphenyl)-2-methylthiomethylpyridine as O-H?N to form chains, and in PdCl2(L1) as O-H?Cl interactions leading to adjacent π-stacked chains oriented in an antiparallel fashion.

TRIAZOLOPYRAZINE COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE & INFLAMMATORY DISEASES

Novel [1.2.4]triazolo[1,5-a]pyrazine compounds are disclosed that have a formula represented by the following (formula I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, arthritis, inflammation, and others.