22282-99-1

Basic information

• Product Name: 4-Bromo-2-methylpyridine
• Synonyms: CHEMBRDG-BB 4014101;2-METHYL-4-BROMOPYRIDINE;4-BROMO-2-METHYLPYRIDINE;4-BROMO-2-METHYL-PYRIDINE HYDROCHLORIDE;4-BROMO-2-METHYL-PYRIDINIUM, CHLORIDE;4-BROMO-2-PICOLINE;4-BROMO-2-PICOLINE HCL;4-BROMO-METHYL-PYRIDINE
• CAS NO: 22282-99-1
• Molecular Formula: C₆H₆BrN
• Molecular Weight: 172.02
• EINECS: -0
• Product Categories: Pyridine;Halides;Heterocycles;Pyridine Series;Pyridines, Pyrimidines, Purines and Pteredines;Heterocyclic Series;pharmacetical;Pyridines;Organohalides;Aromatics Compounds;Bromopyridines;Halopyridines;Aromatics;Boronic Acid;Building Blocks;C5 to C6;C6 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 22282-99-1.mol

Chemical Properties

• Boiling Point: 76 °C / 14mmHg
• Flash Point: 174 °F
• Appearance: Light yellow liquid
• Density: 1.450 g/mL at 25 °C
• Vapor Pressure: 0.581mmHg at 25°C
• Refractive Index: n 20/D 1.556
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Dichloromethane
• PKA: 4.38±0.10(Predicted)
• Water Solubility: Miscible with dichloromethane. Immiscible with water.
• CAS DataBase Reference: 4-Bromo-2-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-methylpyridine(22282-99-1)
• EPA Substance Registry System: 4-Bromo-2-methylpyridine(22282-99-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38-20/21/22
• Safety Statements: 26-36/39-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 22282-99-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Bromo-2-methylpyridine is used as a starting material for the synthesis of crown-ester-bipyridines and viologens through sodium or nickel reductive coupling, side chain oxidation, and esterification. These synthesized compounds have potential applications in various fields, including the development of new materials and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Bromo-2-methylpyridine serves as an important raw material and intermediate for the preparation of phenyloxadiazolyl pyridines, which are known as immunomodulating agents. These agents can help regulate the immune system and are useful in the development of drugs for various medical conditions.
Used in Agrochemicals:
4-Bromo-2-methylpyridine is also utilized as a starting material in the agrochemical industry, where it is used to synthesize various compounds with pesticidal, herbicidal, or fungicidal properties. These compounds can be employed to protect crops from pests and diseases, ensuring higher yields and better quality produce.
Used in Dyes:
In the dye industry, 4-Bromo-2-methylpyridine is used as a key intermediate for the production of various dyes with specific color properties. These dyes can be used in a wide range of applications, such as textiles, plastics, and printing inks, to impart desired colors and enhance the visual appeal of the final products.

InChI:InChI=1/C6H6BrN/c1-5-4-6(7)2-3-8-5/h2-4H,1H3

Upstream product

• 18437-58-6 3-methyl-4-pyridinamine 
• 13508-96-8 2-methyl-4-nitro-pyridine 
• 506-96-7 Acetyl bromide 
• 67-66-3 chloroform 
• 7789-60-8 phosphorus tribromide 
• 19524-06-2 4-bromopyridine hydrochloride 
• 931-19-1 2-methylpyridine N-oxide 
• 5470-66-6 2-methyl-4-nitropyridine N-oxide 
• 75-16-1 methylmagnesium bromide 
• 131747-63-2 4-bromo-2-pyridinecarboxaldehyde 
• 676-58-4 methylmagnesium chloride 
• 23056-36-2 2-chloro-4-nitropyridine 
• 58530-53-3 2,4-dibromopyridine 
• 74-88-4 methyl iodide 

Downstream Products

• 98547-36-5 2-(2-hydroxy-ethyl)-pyridin-4-ol 
• 98280-12-7 2-(4-bromopyridin-2-yl)ethanol 
• 100367-74-6 4-bromo-2-methylpyridine N-oxide 
• 30766-03-1 4-bromo-2-picolinic acid 
• 712-61-8 2,2'-dimethyl-4,4'-bipyridine 
• 131747-63-2 4-bromo-2-pyridinecarboxaldehyde 
• 131747-45-0 4-bromo-2-(hydroxymethyl)pyridine 
• 108337-74-2 2,6-dimethyl-4-(4-bromo-2-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-(N-benzyl-N-methylamino)ethyl ester 5-methyl ester 
• 94413-70-4 1-(2-methylpyridin-4-yl)methanamine 
• 660867-80-1 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 579474-98-9 3-[3-(2-methyl-pyridin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester 
• 134914-97-9 2-methyl-4-(tributylstannyl)pyridine 
• 1032650-53-5 4-bromo-2-(bromomethyl)pyridine 
• 1032650-80-8 4-bromo-2-dibromomethylpyridine 

Relevant articles and documents

Synthesis of atropisomeric 1,8-bis(4′,4′-dipyridyl)naphthalenes from 4-trimethylstannylpyridines

Two synthetic strategies towards atropisomeric 2′,2′-disubstituted 1,8-bis(4′,4′-dipyridyl)naphthalenes using Stille crosscoupling of trimethylstannylpyridine derivatives and 1,8-di-iodonaphthalene have been investigated. Introduction of substituents into the pyridyl moieties prior to the cross-coupling step provides higher overall yields than derivatization of 1,8-bis(4′,4′-dipyridyl)naphthalene under Ziegler reaction conditions.

2-methyl-4-bromopyridine preparation method

The invention belongs to the field of organic synthesis, and particularly relates to a 2-methyl-4-bromopyridine preparation method, which comprises: (1) carrying out a reaction on diethyl malonate andan alkali metal to generate a salt, adding a toluene solution of 2-chloro-4-nitropyridine in a dropwise manner, carrying out a condensation reaction, and decarboxylating under acidic conditions to obtain 2-methyl-4-nitropyridine; (2) carrying out hydrogenation reduction on the 2-methyl-4-nitropyridine under the catalysis of Pd/C by using methanol as a solvent, carrying out suction filtration, andconcentrating the filtrate to obtain 2-methyl-4-aminopyridine; and (3) carrying out a reaction on the 2-methyl-4-aminopyridine and an acid to generate a salt, cooling to -10-0 DEG C, adding bromine in a dropwise manner, adding a sodium nitrite aqueous solution in a dropwise manner, adjusting the pH value of the solution to achieve an alkaline state after the adding, extracting, drying, and concentrating to obtain 2-methyl-4-bromopyridine. According to the invention, the method has beneficial effects of mild reaction conditions, easy operation, simple post-treatment, easy scale-up production,good catalytic effect, high yield, inexpensive raw materials and low production cost, and is suitable for industrial production;.

NOVEL ORGANIC COMPOUND AND MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME AND ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME

The present invention provides a novel organic compound represented by chemical formula 1, a material for an organic electroluminescent device including the organic compound, and an organic electroluminescent device. The present invention can improve color purity and device life.

NOVEL ORGANIC COMPOUND AND MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME AND ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME

The present invention provides a novel organic compound represented by chemical formula 1, a material for an organic electroluminescent device including the organic compound, and an organic electroluminescent device. The present invention can improve thermal stability, color purity, and device life.

A 2 - methyl -4 - bromo pyridine preparation method

The invention belongs to the field of organic synthesis, in particular relates to a 2 - methyl - 4 - bromo pyridine method, comprises the following steps: (1) malonic acid diethyl ester and alkali metal reaction to produce salt, then dropwise 2 - chloro - 4 - nitro pyridine to a toluene solution of a condensation reaction, after decarboxylation under acidic conditions shall be 2 - methyl - 4 nitro pyridine; (2) 2 - methyl - 4 - nitro-pyridine in under the catalysis of the Pd/C, methanol as the solvent, hydrogen reduction, filtered, the filtrate is concentrated, shall be 2 - methyl - 4 - aminopyridine; (3) 2 - methyl - 4 - aminopyridine first with an acid generating salt, cooled to - 10 °C - 0 °C, [...], drops the instillment sodium nitrite aqueous solution, pH adjusting solution is dropped is alkaline, and then extracted, drying, concentration, shall be 2 - methyl - 4 - bromo pyridine. The beneficial effect of the invention is: mild reaction conditions, is easy to operate, after treatment is simple, and easy to enlarge production, is extremely suitable for industrial production; good catalytic effect, high yield; low prices of raw materials, the production cost is low.

Di-substituted pyridinyl aminohydantoins as potent and highly selective human β-secretase (BACE1) inhibitors

The identification of highly selective small molecule di-substituted pyridinyl aminohydantoins as β-secretase inhibitors is reported. The more potent and selective analogs demonstrate low nanomolar potency for the BACE1 enzyme as measured in a FRET assay, and exhibit comparable activity in a cell-based (ELISA) assay. In addition, these pyridine-aminohydantoins are highly selectivity (>500×) against the other structurally related aspartyl proteases BACE2, cathepsin D, pepsin and renin. Our design strategy followed a traditional SAR approach and was supported by molecular modeling studies based on the previously reported aminohydantoin 3a. We have taken advantage of the amino acid difference between the BACE1 and BACE2 at the S2′ pocket (BACE1 Pro70 changed to BACE2 Lys86) to build ligands with >500-fold selectivity against BACE2. The addition of large substituents on the targeted ligand at the vicinity of this aberration has generated a steric conflict between the ligand and these two proteins, thus impacting the ligand's affinity and selectivity. These ligands have also shown an exceptional selectivity against cathepsin D (>5000-fold) as well as the other aspartyl proteases mentioned. One of the more potent compounds (S)-39 displayed an IC50 value for BACE1 of 10 nM, and exhibited cellular activity with an EC50 value of 130 nM in the ELISA assay.

ARYLSULFONAMIDE-BASED MATRIX METALLOPROTEASE INHIBITORS

The present invention provides a compound of formula (I):said compound is inhibitor of MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12 and/or MMP-13, and thus can be employed for the treatment of a disorder or disease characterized by abnormal activity of MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12 and/or MMP- 13. Accordingly, the compound of formula (I) can be used in treatment of disorders or diseases mediated by MMP-2, and/or MMP-8, and/or MMP-9, and/or MMP-12, and/or MMP- 13. Finally, the present invention also provides a pharmaceutical composition.

SMALL ORGANIC MOLECULE REGULATORS OF CELL PROLIFERATION

The present invention makes available methods and reagents for modulating proliferation or differentiation in a cell or tissue comprising contacting the cell with a compound. In certain embodiments, the methods and reagents may be employed to correct or inhibit an aberrant or unwanted growth state, e.g., by antagonizing a normal patched pathway or agonizing smoothened or hedgehog activity.

SMALL ORGANIC MOLECULE REGULATORS OF CELL PROLIFERATION

The present invention makes available methods and reagents for modulating proliferation or differentiation in a cell or tissue comprising contacting the cell with a compound. In certain embodiments, the methods and reagents may be employed to correct or inhibit an aberrant or unwanted growth state, e.g., by antagonizing a normal patched pathway or agonizing smoothened orhedgehog activity.

SMALL ORGANIC MOLECULE REGULATORS OF CELL PROLIFERATION

The present invention makes available methods and reagents for modulating proliferation or differentiation in a cell or tissue comprising contacting the cell with a compound. In certain embodiments, the methods and reagents may be employed to correct or inhibit an aberrant or unwanted growth state, e.g., by antagonizing a normal patched pathway or agonizing smoothened orhedgehog activity.