2-Chloro-6-fluorophenylboronic acid

Base Information

• Chemical Name: 2-Chloro-6-fluorophenylboronic acid
• CAS No.: 313545-32-3
• Molecular Formula: C₆H₅BClFO₂
• Molecular Weight: 174.367
• Hs Code.: 2931900090
• European Community (EC) Number: 811-891-8
• DSSTox Substance ID: DTXSID60393546
• Wikidata: Q72451144
• Mol file: 313545-32-3.mol

Synonyms:2-Chloro-6-fluorophenylboronic acid;313545-32-3;(2-chloro-6-fluorophenyl)boronic acid;2-Chloro-6-fluorobenzeneboronic acid;Boronic acid, (2-chloro-6-fluorophenyl)-;MFCD04039892;(2-chloro-6-fluoro-phenyl)boronic Acid;SCHEMBL321378;DTXSID60393546;NXSZSZJWZVLHAY-UHFFFAOYSA-N;BBL102100;CK2306;STL555899;(2-chloro-6-fluorophenyl)boronicacid;AKOS015850058;AB17456;AM86853;AS-3180;CS-W008070;SY047752;C3247;FT-0649274;A22450;EN300-203090;J-508936;Z1255431725;2-Chloro-6-fluorophenylboronic Acid (contains varying amounts of Anhydride)

Chemical Property of 2-Chloro-6-fluorophenylboronic acid

Chemical Property:

• Melting Point: 131-135 °C(lit.)
• Boiling Point: 299.8 °C at 760 mmHg
• PKA: 8.03±0.58(Predicted)
• Flash Point: 135.1 °C
• PSA: 40.46000
• Density: 1.41 g/cm³
• LogP: 0.15890
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 174.0055154
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-6-fluorophenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC=C1Cl)F)(O)O
• Uses: suzuki reaction Reactant for:Suzuki couplingPreparation of cellular checkpoint kinase Wee1 binding affectors

Technology Process of 2-Chloro-6-fluorophenylboronic acid

There total 2 articles about 2-Chloro-6-fluorophenylboronic 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: 84.0%

Trimethyl borate (121-43-7,63156-11-6) + 3-chlorofluorobenzene (625-98-9) → (2-chloro-6-fluorophenyl)boronic acid (313545-32-3)

Guidance literature:

3-chlorofluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; hexane; water; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.201703591

Reference yield: 82.0%

Triisopropyl borate (5419-55-6) + 3-chlorofluorobenzene (625-98-9) → (2-chloro-6-fluorophenyl)boronic acid (313545-32-3)

Guidance literature:

3-chlorofluorobenzene; With n-butyllithium; In tetrahydrofuran; ethanol; hexane; at -78 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; ethanol; hexane; at -78 - 0 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; ethanol; hexane; water; at 20 ℃; for 0.5h; Inert atmosphere;

Reference yield: 91.0%

naphthalene-1,8-diamine (479-27-6) + (2-chloro-6-fluorophenyl)boronic acid (313545-32-3) → C16H11BClFN2

Guidance literature:

In toluene; for 2h; Dean-Stark; Reflux;

DOI:10.1016/j.chempr.2020.11.017

upstream raw materials:

Trimethyl borate

3-chlorofluorobenzene

Triisopropyl borate

Downstream raw materials:

5-amino-N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-chloro-6-fluorophenyl)thiazole-4-carboxamide

5-amino-N-(5-((2S,5R,6R)-5-amino-6-methoxyoxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-chloro-6-fluorophenyl)thiazole-4-carboxamide

N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-chloro-6-fluorophenyl)thiazole-4-carboxamide

8-bromo-1-chlorodibenzo[b,d]furan

Refernces

• 1、 Dorkó, éva,Szabó, Márk,Kótai, Bianka,Pápai, Imre,Domján, Attila,Soós, Tibor. "Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls". supporting information. p. 9512 - 9516. Retrieved 2017/08/01.