29958-12-1

Basic information

• Product Name: 5-AMINO-2-IODOPYRIDINE
• Synonyms: 5-AMINO-2-IODOPYRIDINE;6-IODOPYRIDIN-3-AMINE;2-IODO-5-AMINOPYRIDINE;5-AMINO-2-IODOPYRIDINE 99%;6-Iodo-pyridin-3-ylaMine
• CAS NO: 29958-12-1
• Molecular Formula: C₅H₅IN₂
• Molecular Weight: 220.01
• EINECS: 1592732-453-0
• Product Categories: Pyridine;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;amine| alkyl Iodine
• Mol File: 29958-12-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 63-67 °C
• Boiling Point: 331.8 °C at 760 mmHg
• Flash Point: 154.5 °C
• Appearance: /
• Density: 2.055 g/cm³
• Vapor Pressure: 0.000152mmHg at 25°C
• Refractive Index: 1.702
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.78±0.10(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 5-AMINO-2-IODOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-2-IODOPYRIDINE(29958-12-1)
• EPA Substance Registry System: 5-AMINO-2-IODOPYRIDINE(29958-12-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41-43
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 29958-12-1(Hazardous Substances Data)

Usage

Description

5-AMINO-2-IODOPYRIDINE is an organic compound with the molecular formula C5H5IN2. It is a heterocyclic compound, specifically a pyridine derivative, which features an amino group at the 5th position and an iodine atom at the 2nd position. 5-AMINO-2-IODOPYRIDINE is known for its potential applications in the pharmaceutical industry due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
5-AMINO-2-IODOPYRIDINE is used as a pharmaceutical intermediate for the synthesis of various drugs, particularly in the development of antitumor antibiotics. Its unique structure allows it to serve as a key building block in the creation of more complex and effective pharmaceutical compounds.
Used in Antitumor Antibiotic Synthesis:
5-AMINO-2-IODOPYRIDINE is specifically utilized as an intermediate in the synthesis of the antitumor antibiotic L-azatyrosine. This antibiotic is known for its potential to inhibit the growth of cancer cells and has shown promise in the treatment of various types of cancer. 5-AMINO-2-IODOPYRIDINE's role in the synthesis process is crucial, as it contributes to the overall effectiveness and potency of the final product.

InChI:InChI=1/C5H5IN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2

Upstream product

• 13534-97-9 6-bromopyridine-3-amine 
• 462-08-8 pyridin-3-ylamine 
• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 4548-45-2 2-chloro-5-nitropyridine 
• 28080-54-8 2-iodo-5-nitropyridine 

Downstream Products

• 856358-16-2 N-acetyl-sulfanilic acid-(6-iodo-[3]pyridylamide) 
• 1206775-61-2 6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl-amine 
• 1206773-59-2 N-(6-{(E)-2-[3-tert-butyl-5-(5-chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-methanesulfonamide 
• 1323276-40-9 (S)-1-(2-cyanophenoxy)-2-hydroxy-3-(2-(1-(4-iodopyrdinyl)ureido-3-yl)ethyl)amino propane 

Relevant articles and documents

Copper-catalyzed conversion of aryl and heteroaryl bromides into the corresponding iodide

An efficient method for the synthesis of aryl and heteroaryl iodides is described in this study. The reactions of aryl and heteroaryl bromides with potassium iodide proceeded smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding iodides in satisfactory to excellent yields.

Synthesis and cardiac imaging of 18F-ligands selective for β1-adrenoreceptors

A series of potent and selective β1-adrenoreceptor ligands were identified (IC50 range, 0.04-0.25 nM; β1/ β2 selectivity range, 65-450-fold), labeled with the PET radioisotope fluorine-18 and evaluated in normal Sprague-Dawley rats. Tissue distribution studies demonstrated uptake of each radiotracers from the blood pool into the myocardium (0.48-0.62% ID/g), lung (0.63-0.97% ID/g), and liver (1.03-1.14% ID/g). Dynamic μPET imaging confirmed the in vivo dissection studies.

A revised synthesis of the antitumour antibiotic L-azatyrosine via 2-iodo-5-methoxypyridine

A revised synthesis of the antitumour antibiotic L-azatyrosine is reported, the main features of which are the unambiguous synthesis of the previously misinterpreted 2-iodo-5-methoxypyridine and subsequent palladium-catalysed coupling with an iodoalanine-derived zinc reagent.