2-Chloro-3-hydroxypyridine

Base Information

• Chemical Name: 2-Chloro-3-hydroxypyridine
• CAS No.: 6636-78-8
• Molecular Formula: C5H4ClNO
• Molecular Weight: 129.546
• Hs Code.: 29333990
• European Community (EC) Number: 229-635-3
• NSC Number: 18469
• UNII: VY212Q0S3J
• DSSTox Substance ID: DTXSID3022243
• Nikkaji Number: J51.351B
• Wikidata: Q27292085
• ChEMBL ID: CHEMBL4636200
• Mol file: 6636-78-8.mol

Synonyms:2-chloro-3-hydroxypyridine

Chemical Property of 2-Chloro-3-hydroxypyridine

Chemical Property:

• Appearance/Colour: light beige powder
• Vapor Pressure: 0.000225mmHg at 25°C
• Melting Point: 168-172 °C
• Refractive Index: 1.583
• Boiling Point: 316.2 °C at 760 mmHg
• PKA: 4.32±0.10(Predicted)
• Flash Point: 145 °C
• PSA: 33.12000
• Density: 1.392 g/cm³
• LogP: 1.44060
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.9981414
• Heavy Atom Count: 8
• Complexity: 78.8

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-3-hydroxypyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-24/25-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)Cl)O
• Uses: 2-Chloro-3-hydroxypyridine has been used in the preparation of 3-hydroxypyridine-2( 1 H)-selone. It has also been used in the synthesis of all four possible benzo[4,5]furopyridine tricyclic heterocycles: benzo[4,5]furo[2,3-b]pyridine, benzo[4,5]furo[2,3-c]pyridine, benzo[4,5]furo[3,2-c]pyridine, and benzo[4,5]furo[3,2-b]pyridine. the synthesis involves α and γ-activation of chloropyridines, as well as palladium-mediated reactions.

Technology Process of 2-Chloro-3-hydroxypyridine

There total 22 articles about 2-Chloro-3-hydroxypyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(2-Chloro-pyridin-3-yloxy)-acetonitrile → 2-chloro-3-hydroxypyridine (6636-78-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol;

DOI:10.1016/S0040-4039(00)60401-X

Reference yield: 95.0%

2-chloropyridin-3-yl trifluoromethanesulfonate (163083-47-4) → 2-chloro-3-hydroxypyridine (6636-78-8)

Guidance literature:

With caesium carbonate; In toluene; at 80 ℃; for 15h;

DOI:10.1016/j.tetlet.2013.10.087

Reference yield: 81.0%

(2-chloropyridin-3-yl)boronic acid (381248-04-0) → 2-chloro-3-hydroxypyridine (6636-78-8)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; water; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2004.12.006

upstream raw materials:

3-HYDROXYPYRIDINE

2-chloro-3-aminopyridine

2-bromo-3-ethoxypyridine

3-hydroxy-2-nitropyridine

Downstream raw materials:

2-chloro-6-(hydroxymethyl)-3-pyridinol

2-chloro-3-hydroxy-6-iodo-pyridine

2-chloro-3-[(5-nitro-2-pyridinyl)oxy]pyridine

4-chloro-benzenesulfonic acid 2-chloro-4,6-diiodo-pyridin-3-yl ester

Refernces

• 1、 -. "Method for preparing 2,3-dichloropyridine". Paragraph 0022; 0023; 0024; 0025; 0026; 0027; 0029. . Retrieved 2017/08/28.
• 2、 Voisin, Anne Sophie,Bouillon, Alexandre,Lancelot, Jean-Charles,Rault, Sylvain. "Efficient synthesis of halohydroxypyridines by hydroxydeboronation". . p. 1417 - 1421. Retrieved 2007/10/03.