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

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

Uses

Used in Pharmaceutical Synthesis:
2-Chloro-3-hydroxy-6-iodopyridine is used as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and medications. Its unique structure allows for the creation of complex organic molecules that can be utilized in the formulation of therapeutic agents.
Used in Agrochemical Production:
2-Chloro-3-hydroxy-6-iodopyridine is also used as an intermediate in the synthesis of agrochemicals, playing a role in the development of pesticides, herbicides, and other agricultural chemicals. Its reactivity and structural properties make it a key component in the production of these substances.
Used in Organic Synthesis:
2-Chloro-3-hydroxy-6-iodopyridine is employed as a reagent in organic synthesis, where it can be used to create a variety of complex organic compounds. Its versatility in chemical reactions makes it a valuable tool for chemists working on the synthesis of new molecules.
Used in Chemical Research and Development:
In the field of chemical research and development, 2-Chloro-3-hydroxy-6-iodopyridine is used for its potential in creating new chemical entities and exploring novel reaction pathways. Its unique properties make it an important tool for advancing the understanding of organic chemistry and the development of new chemical processes.

Upstream product

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

Downstream Products

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

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.

Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates

The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.

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.

Inhibitors of α4β1 mediated cell adhesion

The present invention relates to compound of formula (I), that are potent inhibitors of α4β1mediated adhesion to either VCAM or CS-1 and which could be useful for the treatment of inflammatory diseases. Specifically, the molecules of the present invention can be used for treating or preventing α4β1adhesion mediated conditions in a mammal such as a human. This method may comprise administering to a mammal or a human patient an effective amount of the compound or composition as explained in the present specification.

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.

Alpha-substituted pyrimidine-thioalkyl and alkylether compounds as inhibitors of viral reverse transcriptase

The subject invention relates to pyrimidine-thioalkyl and alkylether compounds of Formula (I) and pyrimidine-thioalkyl and alkylethers of Formula (IA), namely the compounds of Formula (I) where R 4 is selected from the group consisitng of --H or --NR 15 R 16 where R 15 is --H and R 16 is --H, C 1 -C 6 alkyl, NH 2 or R 15 and R 16 taken together with the --N form 1-pyrrolidino, 1-morpholino or 1-piperidino; and R 6 is selected from the group consisting of --H, or halo (preferably --Cl); with the overall proviso that R 4 and R 6 are not both --H. The compounds of Formula (IA) are useful in the treatment of individuals who are HIV positive being inhibitors of viral reverse transcriptase. STR1

Stereoselective synthesis of furo[2,3-c]pyridine pyrimidine thioethers, a new class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors

An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU- 109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.