185220-68-2

Basic information

• Product Name: 2-Chloro-3-hydroxy-6-iodopyridine
• Synonyms: 2-Chloro-3-hydroxy-6-iodopyridine;2-chloro-6-iodopyridin-3-ol;2-chloro-3-hydroxy-6-iodo-pyridin;3-Pyridinol,2-chloro-6-iodo-;2-chloro-6-iodo-3-pyridinol >97%
• CAS NO: 185220-68-2
• Molecular Formula: C₅H₃ClINO
• Molecular Weight: 255.44
• Mol File: 185220-68-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 141-145°C
• Boiling Point: 394.5±42.0 °C(Predicted)
• Appearance: /
• Density: 2.219±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.96±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-3-hydroxy-6-iodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-hydroxy-6-iodopyridine(185220-68-2)
• EPA Substance Registry System: 2-Chloro-3-hydroxy-6-iodopyridine(185220-68-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 185220-68-2(Hazardous Substances Data)

Usage

General Description

2-Chloro-3-hydroxy-6-iodopyridine is a chemical compound that is a derivative of pyridine. It consists of a pyridine ring with chlorine and iodine atoms attached at specific positions, and a hydroxyl group attached to the carbon adjacent to the chlorine atom. 2-Chloro-3-hydroxy-6-iodopyridine is often used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. Its unique structure and reactivity make it a valuable building block for the production of various complex organic molecules. Additionally, 2-Chloro-3-hydroxy-6-iodopyridine is known for its potential as a reagent in organic synthesis and for its use in chemical research and development. Overall, this compound has a wide range of applications and is an important tool in the field of organic chemistry.

Upstream product

• 6636-78-8 2-chloro-3-hydroxypyridine 
• 127-65-1 chloroamine-T 

Downstream Products

• 934965-63-6 4-chloro-benzenesulfonic acid 2-chloro-4,6-diiodo-pyridin-3-yl ester 
• 495380-60-4 (3R,αS)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)-3-(N-α-methyl-4-methoxybenzylamino)propanoate 
• 199168-12-2 (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-(6-chloro-5-methoxymethoxy-pyridin-2-yl)-propionic acid tert-butyl ester 
• 219497-41-3 2-Chloro-3-[(2,6-dichlorophenyl)methoxy]-6-iodopyridine 
• 185221-60-7 3-(benzyloxy)-2-chloro-6-iodopyridine 
• 1542143-48-5 2-(benzyloxy)-3-(methoxymethoxy)-6-(4-methoxyphenyl)pyridine 
• 1542143-53-2 2-(benzyloxy)-6-(4-methoxyphenyl)pyridin-3-yl trifluoromethanesulfonate 
• 1542143-58-7 2-(benzyloxy)-6-(4-methoxyphenyl)-3-(p-tolyl)pyridine 
• 1542143-61-2 6-(4-methoxyphenyl)-3-(p-tolyl)pyridin-2-yl trifluoromethanesulfonate 
• 1542143-65-6 4-(6-(4-methoxyphenyl)-3-(p-tolyl)pyridin-2-yl)benzonitrile 
• 1584733-25-4 C₁₉H₁₇NO₃ 
• 1542143-41-8 2-chloro-3-(methoxymethoxy)-6-(4-methoxyphenyl)pyridine 
• 1584733-80-1 C₁₉H₁₇NO₂ 

Relevant articles and documents

Fully regiocontrolled polyarylation of pyridine

Starting from commercially available 2-chloro-3-hydroxypyridine, a new route leading to the first protypical pentaarylpyridine bearing five different substituents is reported. This strategy involves a set of five sequential but fully regiocontrolled Suzuki-Miyaura reactions and highlights the 2-OBn pyridine protecting group as a key intermediate. The 2-OBn group played a double role: (i) it allowed additional bromination at position 5 and (ii) it could afford the reactive OTf species for the last C-arylation step at the less hindered 2 position of the tetraarylpyridine. The photophysical properties of the novel compounds are also described. The synthesized pentaarylpyridine derivative exhibit a large Stokes shift, strong solvatochromism, and quantum yield values up to 0.47; thus, they constitute promising building blocks for the design of environment-sensitive probes.

Nitrogen-containing aromatic derivatives

Compounds represented by the following general formula: [wherein Ag is an optionally substituted 5- to 14-membered heterocyclic group, etc.; Xg is —O—, —S—, etc.; Yg is an optionally substituted C6-14 aryl group, an optionally substituted 5- to 14-membered heterocyclic group, etc.; and Tg1 is a group represented by the following general formula: (wherein Eg is a single bond or —N(Rg2)—, Rg1 and Rg2 each independently represent a hydrogen atom, an optionally substituted C1-6 alkyl group, etc. and Zg represents a C1-8 alkyl group, a C3-8 alicyclic hydrocarbon group, a C6-14 aryl group, etc.)], salts thereof or hydrates of the foregoing.

Asymmetric synthesis of β-pyridyl-β-amino acid derivatives

The conjugate additions of homochiral lithium (R)-N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(3-pyridyl)- and tert-butyl 3-(4-pyridyl)-prop-2-enoates proceed in 84% de, and after subsequent recrystallisation and oxidative N-deprotection furnish the (S)-3-(3-pyridyl)- and (S)-3-(4-pyridyl)-β-amino acid derivatives in 97% ee and 98% ee respectively. Conjugate additions of lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(2-pyridyl)prop-2-enoates proceed with low levels of diastereoselectivity unless the 3-(2-pyridyl) ring is substituted. Application of this methodology allows the asymmetric synthesis of (R)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)-3-aminopropanoate, the protected β-amino ester component of kedarcidin, in 97% ee.