335031-01-1

Basic information

• Product Name: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine
• Synonyms: (2-AMINO-5-BROMO-3-PYRIDINYL)METHANOL;(2-AMINO-5-BROMO-PYRIDIN-3-YL)-METHANOL;2-Amino-5-bromopyridine-3-methanol;2-Amino-5-bromo-3-(hydroxymethyl)pyridine;2-Amino-5-Bromo-3-(Hydroxymeth;2-Amino-5-bromo-3-pyridinemethanol;2-broMo-4-ethoxypyriMidine;2-AMino-3-hydroxyMethyl-5-broMopyridine
• CAS NO: 335031-01-1
• Molecular Formula: C₆H₇BrN₂O
• Molecular Weight: 203.04
• Product Categories: pharmacetical;Pyridine series;Hydroxymethyl's;Pyridines;Pyridine;Heterocyclic Compounds;Aromatics;Heterocycles;Heterocycle-Pyridine series
• Mol File: 335031-01-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 137-140°C
• Boiling Point: 343.5 °C at 760mmHg
• Flash Point: 161.6 °C
• Appearance: Off-white to yellow/Solid
• Density: 1.766 g/cm³
• Vapor Pressure: 2.67E-05mmHg at 25°C
• Refractive Index: 1.665
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Acetone, Ethyl Acetate, Methanol
• PKA: 13.16±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine(335031-01-1)
• EPA Substance Registry System: 2-Amino-5-bromo-3-(hydroxymethyl)pyridine(335031-01-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 335031-01-1(Hazardous Substances Data)

Usage

Description

2-Amino-5-bromo-3-(hydroxymethyl)pyridine is an organic compound characterized by its unique molecular structure featuring a pyridine ring with a bromine atom at the 5th position, an amino group at the 2nd position, and a hydroxymethyl group at the 3rd position. 2-Amino-5-bromo-3-(hydroxymethyl)pyridine is known for its potential applications in various chemical and pharmaceutical processes due to its versatile functional groups.

Uses

Used in Organic Synthesis:
2-Amino-5-bromo-3-(hydroxymethyl)pyridine is used as an organic synthesis intermediate for the creation of various complex organic molecules. Its unique structure allows for multiple points of reactivity, making it a valuable building block in the synthesis of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Amino-5-bromo-3-(hydroxymethyl)pyridine is utilized as a pharmaceutical intermediate. Its presence in the molecular structure of various drugs aids in the development of new therapeutic agents, particularly those targeting specific biological pathways or receptors.
Used in Laboratory Research and Development:
2-Amino-5-bromo-3-(hydroxymethyl)pyridine is also employed in laboratory research and development processes. Its unique properties make it an essential compound for studying various chemical reactions and exploring new methodologies in organic chemistry and drug discovery.
Used in Chemical Production Process:
Furthermore, 2-Amino-5-bromo-3-(hydroxymethyl)pyridine is used in the chemical production process, where it serves as a key intermediate in the manufacturing of various specialty chemicals and materials with specific applications in different industries.

Synthesis

2-Amino-5-bromo-3-(hydroxymethyl)pyridineBromine (8.4 mL, 189.4 mmol) was added dropwise over 1 hour to a solution of 2- amino-3-(hydroxymethyl)pyridine (19.6 g, 157.8 mmol) in acetic acid (350 mL) at room temperature. The reaction mixture was then stirred overnight. After concentration to dryness, the residue was partitioned between a saturated solution of potassium carbonate (300 mL) and ethyl acetate (200 ml_). The aqueous layer was separated and extracted with ethyl acetate (2 x 200 ml_). The combined organic phases were washed with a saturated solution of sodium chloride (200 ml_), dried over sodium sulfate, filtered and concentrated to dryness. After trituration of the residue in pentane, the title product was obtained as a yellow solid (27.0 g, 84%).

InChI:InChI=1/C6H7BrN2O/c7-5-1-4(3-10)6(8)9-2-5/h1-2,10H,3H2,(H2,8,9)

Upstream product

• 23612-57-9 (2-amino-3-pyridinyl)methanol 
• 5345-47-1 2-aminopyridin-3-carboxylic acid 
• 52833-94-0 2-amino-5-bromonicotinicacid 

Downstream Products

• 335033-38-0 2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide 
• 335032-38-7 6-bromo-2-oxo-1,4-dihydro-2 H-pyrido[2,3-d ]-1,3-oxazine 
• 1267849-59-1 1-(4-(6-amino-5-(hydroxymethyl)pyridin-3-yl)phenyl)-3-(5-tert-butylisoxazol-3-yl)urea 
• 1267854-16-9 (2-amino-5-(4-aminophenyl)pyridin-3-yl)methanol 
• 709649-95-6 7-bromo-4-(4-methoxy-benzyl)-1,3,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-2-one 
• 709649-96-7 (E)-3-[4-(4-methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid tert-butyl ester 
• 709649-93-4 (E)-3-[4-(4-methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid hydrochloride 
• 129686-16-4 6-bromo-3,4-dihydro-1,8-naphthyridine-2(1H)-one 
• 941604-37-1 tert-butyl 6-bromo-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-1'-carboxylate 
• 335031-10-2 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylic acid methyl ester 
• 1309205-56-8 6-{(1E)-3-[4-hydroxy-4-phenylpiperidin-1-yl]-3-oxoprop-1-en-1-yl}-3,4-dihydro-1,8-naphthyridin-2(1H)-one 
• 1309205-75-1 methyl 6-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate 
• 1309351-04-9 3-(hydroxymethyl)-6-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one 
• 1309208-23-8 methyl 2-(((2-amino-5-bromopyridin-3-yl)methyl)(4-methoxybenzyl)amino)acetate 

Relevant articles and documents

Novel method for synthesizing 6-bromine-3,4-dihydro-1H-[1,8] naphthyridine-2-ketone

The invention discloses a novel method for synthesizing 6-bromine-3,4-dihydro-1H-[1,8] naphthyridine-2-ketone and relates to the field of chemical synthesis. The method comprises the following steps:by using a four-step synthesis method, performing hydrogen substitution on a benzene ring on 2-amino-3-hydroxymethylpyridine by using bromine so as to generate 2-amino-3-hydroxymethyl-5-bromopyridine;substituting hydroxyl in the 2-amino-3-hydroxymethyl-5-bromopyridine by using chlorine in thionyl chloride so as to generate 2-amino-3-methyl chloride-5-bromopyridine hydrochloride; carrying out an annulation reaction of the 2-amino-3-methyl chloride-5-bromopyridine hydrochloride by using diethyl malonate so as to generate 6-bromine-3-nonanoic acid-ethyl ester-1,2,3,5-tetrahydro-1,8-naphthyridine-2-ketone; finally, under an alkali condition, removing carboxylic acid carbethoxy from the 6-bromine-3-nonanoic acid-ethyl ester-1,2,3,5-tetrahydro-1,8-naphthyridine-2-ketone, thereby obtaining a final product, namely 6-bromine-3,4-dihydro-1H-[1,8] naphthyridine-2-ketone. The method is low in raw material cost, simple in synthesis process, not harsh in reaction condition, safe and convenient to operate, high in final product yield, and applicable to large-scale industrial production.

NOVEL HETEROCYCLIC ACRYLAMIDES AND THEIR USE AS PHARMACEUTICALS

The invention relates to novel heterocyclic acrylamide compounds (I), to the preparation of the compounds and intermediates used therein, to the use of the compounds as antibacterial medicaments and pharmaceutical compositions containing the compounds.

Methods of agonizing and antagonizing FabK

The invention provides methods for using agonists and antagonists of FabK polypeptides, particularly to modulate the metabolism of bacteria or to treat bacterial infection.