98198-48-2

Basic information

• Product Name: 2-Amino-5-bromo-4-methylpyridine
• Synonyms: 5-BROMO-4-METHYL-PYRIDIN-2-YLAMINE;5-BROMO-4-METHYL-2-PYRIDINYLAMINE;2-AMINO-5-BROMO-GAMMA-PICOLINE;2-AMINO-5-BROMO-4-METHYLPYRIDINE;2-AMINO-5-BROMO-4-PICOLINE;2-AMINO-4-METHYL-5-BROMOPYRIDINE;2-Amino-5-bromo-4-methylpyridine 98%;2-AMINO-5-BROMO-4-PICOLINE (2-AMINO-5-BROMO-4-METHYLPYRIDINE)
• CAS NO: 98198-48-2
• Molecular Formula: C₆H₇BrN₂
• Molecular Weight: 187.04
• EINECS: -0
• Product Categories: Amines;blocks;Bromides;Pyridines;Pyridine;Bromopyridines;Halopyridines;Boronic Acid;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Amino-pyridine series
• Mol File: 98198-48-2.mol

Chemical Properties

• Melting Point: 148-151 °C(lit.)
• Boiling Point: 254.2 °C at 760 mmHg
• Flash Point: 107.5 °C
• Appearance: Cream/Powder
• Density: 1.5672 (rough estimate)
• Vapor Pressure: 0.0175mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Soluble in methanol.
• PKA: 5.27±0.24(Predicted)
• CAS DataBase Reference: 2-Amino-5-bromo-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-bromo-4-methylpyridine(98198-48-2)
• EPA Substance Registry System: 2-Amino-5-bromo-4-methylpyridine(98198-48-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 98198-48-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-bromo-4-methylpyridine is used as a pharmaceutical intermediate for the synthesis of a wide range of medications. Its versatile chemical structure allows it to be a key component in the development of drugs targeting various therapeutic areas, such as cardiovascular, neurological, and anti-inflammatory treatments.
Used in Agrochemical Industry:
In addition to its pharmaceutical applications, 2-Amino-5-bromo-4-methylpyridine is also utilized as an intermediate in the production of agrochemicals. Its chemical properties make it suitable for the synthesis of pesticides, herbicides, and other crop protection agents, contributing to enhanced crop yields and food security.
Used in Research and Development:
2-Amino-5-bromo-4-methylpyridine serves as a valuable compound in the field of scientific research and development. It is employed in the synthesis of novel compounds for biological and medicinal studies, as well as in the development of new synthetic methodologies and chemical reactions. This contributes to the advancement of knowledge in organic chemistry and the discovery of new therapeutic agents.

InChI:InChI=1/C6H7BrN2/c1-4-2-6(8)9-3-5(4)7/h2-3H,1H3,(H2,8,9)/p+1

Upstream product

• 142404-82-8 N-(5-bromo-4-methylpyridin-2-yl)acetamide 
• 5327-32-2 2-acetylamino-4-methylpyridine 
• 695-34-1 2-Amino-4-methylpyridine 

Downstream Products

• 179555-10-3 2-amino-5-cyano-4-methylpyridine 
• 142404-82-8 N-(5-bromo-4-methylpyridin-2-yl)acetamide 
• 884495-14-1 5-bromo-2-methoxy-4-methyl-3-nitropyridine 
• 228410-90-0 2-hydroxy-5-bromo-4-methyl-3-nitropyridine 
• 917918-81-1 2-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-N,N-dimethylethenamine 
• 917918-82-2 C₁₁H₁₅N₃O₄ 
• 364046-14-0 4-[(2-di-N,N-methylamino)vinyl]-2-methoxy-3-nitropyridine 
• 917918-79-7 4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridine hydrochloride 
• 917918-83-3 C₈H₇ClN₂O*ClH 
• 1150310-08-9 C₈H₇ClN₂O*Cl₂HO₂P 
• 676491-46-6 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine 
• 701213-99-2 4-methoxy-7-(5-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine 
• 701214-00-8 methyl 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate 
• 701213-36-7 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione 

Relevant articles and documents

Preparation of a novel 1,4-pyridylphenylene derivative for synthesis of new rigid backbone conjugated polymers

High yield synthesis of 1,4-bis-(2-bromo-4-methyl-5-pyridyl)-benzene as monomer for conjugated polymers.

Directing Group Enables Electrochemical Selectively Meta-Bromination of Pyridines under Mild Conditions

Without the use of catalysts and oxidants, a facile and sustainable electrochemical bromination protocol was developed. By introducing the directing groups, the regioselectivity of pyridine derivatives could be controlled at themeta-position utilizing the inexpensive and safe bromine salts at room temperature. A variety of brominated pyridine derivatives were obtained in 28-95% yields, and the reaction could be readily performed at a gram scale. By combining the installation and removing the directing group, the concept ofmeta-bromination of pyridines could be verified.

Preparation of the HIV Attachment Inhibitor BMS-663068. Part 1. Evolution of Enabling Strategies

The development of two enabling routes that led to the production of >1000 kg of BMS-663068 (3) is described. The route identified for the initial 100 kg delivery to support development activities and initial clinical trials involved the conversion of 2-amino-4-picoline to the parent active pharmaceutical ingredient (API), followed by pro-drug installation and deprotection. To eliminate the problematic isolation of the parent API and synthesis of di-t-butyl(chloromethyl)phosphate, a second-generation pro-drug installation route was developed which involved the conversion of a late-stage common intermediate to an N(1)-thioether derivative followed by chloromethylation, displacement with di-t-butylpotassium phosphate, and deprotection. This second strategy resulted in the multikilogram scale preparation of the API in 14 linear steps and ～7% overall yield.

Scalable synthesis and properties of 7-methyl-4-azaindole

An approach to the synthesis of 7-methyl-4-azaindole, which is a valuable building block for drug discovery programs, is described. The method relies on using a bromine atom as a 'place holding group' for one of the carbon atoms of the pyridine ring throughout the reaction sequence, and it is removed only upon the final reductive cyclization leading to the azaindole ring. Exhaustive hydrogenation of the target product proceeds in a diastereoselective manner and leads to a bicyclic conformationally restricted diamine derivative.

A mild method for the regioselective bromination of 2-aminopyridines

An efficient and regioselective bromination of 2-aminopyridines was developed. The environmental friendly bromination occurs under mild and clean conditions using readily available 1-butylpyridinium bromide as the bromine source and hydrogen peroxide as the green oxidant.

Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses

Bioisosteric deaza analogues of 6-methyl-9-β-d-ribofuranosylpurine, a hydrophobic analogue of adenosine, were synthesized and evaluated for antiviral activity. Whereas the 1-deaza and 3-deaza analogues were essentially inactive in plaque assays of infectivity, a novel 7-deaza-6-methyl-9-β-d- ribofuranosylpurine analogue, structurally related to the natural product tubercidin, potently inhibited replication of poliovirus (PV) in HeLa cells (IC50 = 11 nM) and dengue virus (DENV) in Vero cells (IC50 = 62 nM). Selectivity against PV over cytotoxic effects to HeLa cells was >100-fold after incubation for 7 h. Mechanistic studies of the 5′-triphosphate of 7-deaza-6-methyl-9-β-d-ribofuranosylpurine revealed that this compound is an efficient substrate of PV RNA-dependent RNA polymerase (RdRP) and is incorporated into RNA mimicking both ATP and GTP.

CYCLOALKANOPYRIDINE DERIVATIVE

Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.

Stereoselective synthesis of conformationally constrained tropane analogues: 6-Chloro-2,5-diazatetracyclo[8.5.0.02,13.0 4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.02,13.04,9]pentadeca-4,6,8-triene-11-one

Two conformationally constrained tropane derivatives were prepared as rigid nicotinic acetylcholine receptor ligands. A palladium catalyzed intramolecular α-arylation reaction was employed to generate the tricyclic compounds in good yields from N-(bromo-chloropyridylmethyl)-8-azabicyclo[3.2.1]octan-3-ones.

Design and synthesis of potent, orally active, inhibitors of carboxypeptidase U (TAFIa)

A series of 3-mercapto-propionic acid derivatives that function as reversible inhibitors of carboxypeptidase U have been prepared. We present a successful design strategy using cyclic, low basicity guanidine mimetics resulting in potent, selective and bioavailable inhibitors of carboxypeptidase U (TAFIa).

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Substituted 2-aminopyridine compounds of Formula (I) and pharmaceutically acceptable salts which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders. STR1