2-Chloro-4-pyridylboronic acid

Base Information

• Chemical Name: 2-Chloro-4-pyridylboronic acid
• CAS No.: 458532-96-2
• Molecular Formula: C5H5BClNO2
• Molecular Weight: 157.364
• Hs Code.: 29333990
• European Community (EC) Number: 628-060-9
• ChEMBL ID: CHEMBL3236585
• DSSTox Substance ID: DTXSID90408874
• Nikkaji Number: J1.748.336F
• Wikidata: Q72458837
• Mol file: 458532-96-2.mol

Synonyms:458532-96-2;2-Chloropyridine-4-boronic acid;2-Chloro-4-pyridylboronic acid;(2-chloropyridin-4-yl)boronic Acid;2-Chloro-4-pyridineboronic acid;2-chloropyridin-4-ylboronic acid;2-CHLORO-4-PYRIDINYLBORONIC ACID;MFCD03788416;2-chloropyridin-4-yl boronic acid;(2-chloro-4-pyridinyl)boronic acid;2-chloropyridin-4-yl-4-boronic acid;BORONIC ACID, (2-CHLORO-4-PYRIDINYL)-;2-CHLOROPYRIDIN-4-BORONIC ACID;SCHEMBL200588;CHEMBL3236585;2-chloropyrid-4-yl boronic acid;DTXSID90408874;2-chloro-4-pyridine boronic acid;2-chloro-pyridine-4-boronic acid;WJYRVVDXJMJLTN-UHFFFAOYSA-N;2-chloro-pyridin-4-ylboronic acid;(2-chloropyridin-4-yl)boronicAcid;CS-D1048;2-chloro-pyridin-4-yl-boronic acid;RB2042;AKOS004119272;AB15988;AC-6990;GS-6579;HY-32954;SY006037;A7191;AM20070092;C2589;FT-0644701;2-Chloro-4-pyridinylboronic acid, >=95.0%;EN300-62789;J-500721;J-500723;Z985148286;2-Chloro-4-pyridylboronic Acid

Chemical Property of 2-Chloro-4-pyridylboronic acid

Chemical Property:

• Appearance/Colour: WHITE TO TAN POWDER
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 155-163 °C
• Refractive Index: 1.559
• Boiling Point: 355.186 °C at 760 mmHg
• PKA: 6.57±0.10(Predicted)
• Flash Point: 168.611 °C
• PSA: 53.35000
• Density: 1.41 g/cm³
• LogP: -0.58520
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 157.0101863
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99% ^*data from raw suppliers

2-Chloropyridine-4-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=NC=C1)Cl)(O)O
• Uses: 2-Chloropyridine-4-boronic Acid is a substrate in a peroxide mediated hydroxydeboronation providing good yields of halohydroxypyridines. It is also a reagent used to prepare IRAK-4 inhibitors. Substrate in a peroxide mediated hydroxydeboronation providing good yields of halohydroxypyridines.

Technology Process of 2-Chloro-4-pyridylboronic acid

There total 2 articles about 2-Chloro-4-pyridylboronic acid 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: 64.0%

2-chloro-4-bromopyridine (73583-37-6) → 2-chloropyridine-4-boronic acid (458532-96-2)

Guidance literature:

2-chloro-4-bromopyridine; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at -60 ℃; for 0.5h;

With Triisopropyl borate; In diethyl ether; at -70 - 20 ℃;

With sodium hydroxide; In diethyl ether; water;

DOI:10.1016/S0040-4020(02)00416-7

Reference yield:

2-chloro-4-bromopyridine (73583-37-6) + Trimethyl borate (121-43-7,63156-11-6) → 2-chloropyridine-4-boronic acid (458532-96-2)

Guidance literature:

2-chloro-4-bromopyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

Trimethyl borate; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

DOI:10.1021/acs.orglett.6b01681

Reference yield: 80.0%

3-iodo-4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (1367874-97-2) + 2-chloropyridine-4-boronic acid (458532-96-2) → 3-(2-chloropyridin-4-yl)-4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (1367874-85-8)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; acetonitrile; at 100 ℃; for 0.666667h; Inert atmosphere; Microwave irradiation;

upstream raw materials:

2-chloro-4-bromopyridine

Trimethyl borate

Downstream raw materials:

2,2'-dichloro-3,4'-bipyridine

2-chloropyridin-4-ol

1-[3-(2-Chloro-pyridin-4-yl)-phenyl]-ethanone

3-(2-chloropyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valérie,Bovy, Philippe R,Rault, Sylvain. "Synthesis of novel halopyridinylboronic acids and esters. Part 3: 2, or 3-Halopyridin-4-yl-boronic acids and esters". . p. 4369 - 4373. Retrieved 2007/10/03.