5-Chloro-2-fluorophenylboronic acid

Base Information

• Chemical Name: 5-Chloro-2-fluorophenylboronic acid
• CAS No.: 352535-83-2
• Molecular Formula: C₆H₅BClFO₂
• Molecular Weight: 174.367
• Hs Code.: 29319090
• European Community (EC) Number: 675-613-5
• DSSTox Substance ID: DTXSID60395469
• Wikidata: Q72450511
• Mol file: 352535-83-2.mol

Synonyms:5-Chloro-2-fluorophenylboronic acid;352535-83-2;(5-chloro-2-fluorophenyl)boronic acid;5-Chloro-2-fluorobenzeneboronic acid;Boronic acid, (5-chloro-2-fluorophenyl)-;MFCD05664225;(5-chloro-2-fluoro-phenyl)boronic Acid;SCHEMBL246398;DTXSID60395469;GGTUVWGMCFXUAS-UHFFFAOYSA-N;BCP15299;NNNN-TETRAETHYLTEREPHTHALAMIDE;BBL102091;STL555890;(5-chloro-2-fluorophenyl)boronicacid;5-chloro-2-fluorophenyl boronic acid;AKOS004113770;AB22317;AM86895;CS-W003241;GS-6268;SY032671;A6191;C2645;FT-0644495;EN300-396458;J-517304;Z421825736;5-Chloro-2-FluorophenylboronicAcid;5-CHLORO-2-FLUOROPHENYLBORONIC ACID

Chemical Property of 5-Chloro-2-fluorophenylboronic acid

Chemical Property:

• Vapor Pressure: 0.000252mmHg at 25°C
• Melting Point: 122-127 °C(lit.)
• Refractive Index: 1.533
• Boiling Point: 310.8 °C at 760 mmHg
• PKA: 7.35±0.58(Predicted)
• Flash Point: 141.8 °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

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC(=C1)Cl)F)(O)O
• Uses: suzuki reaction Reactant involved in:Suzuki cross-coupling reactionsSynthesis of biaryl amides with muscarinic acetylcholine receptor subtype M1 agonistic activitySynthesis of kinesin spindle protein inhibitorsGABA α2/3 agonist preparation

Technology Process of 5-Chloro-2-fluorophenylboronic acid

There total 4 articles about 5-Chloro-2-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: 90.0%

1-Chloro-4-fluorobenzene (352-33-0) → 5-chloro-2-fluorophenylboronic acid (352535-83-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; Triisopropyl borate; n-hexyllithium; In tetrahydrofuran; hexane; at -75 - -50 ℃; for 5h; Inert atmosphere;

DOI:10.1021/op050217j

Reference yield: 78.3%

2-bromo-4-chloro-1-fluorobenzene (1996-30-1) + Trimethyl borate (121-43-7,63156-11-6) + water (7732-18-5) → 5-chloro-2-fluorophenylboronic acid (352535-83-2)

Guidance literature:

2-bromo-4-chloro-1-fluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

Trimethyl borate; In tetrahydrofuran; hexane; for 0.5h;

water; With hydrogenchloride; In tetrahydrofuran; hexane; at 20 ℃;

Reference yield: 62.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-Chloro-4-fluorobenzene (352-33-0) → 5-chloro-2-fluorophenylboronic acid (352535-83-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; cyclohexane; at -50 ℃; Flow reactor;

DOI:10.1021/op500213j

upstream raw materials:

1-Chloro-4-fluorobenzene

Trimethyl borate

2-bromo-4-chloro-1-fluorobenzene

Triisopropyl borate

Refernces

• 1、 -. "COMPOUNDS AND METHODS OF USE". Paragraph 0130. . Retrieved 2015/07/16.
• 2、 Cameron, Mark,Foster, Bruce S.,Lynch, Joseph E.,Shi, Yao-Jun,Dolling, Ulf-H.. "The expedient synthesis of 4,2′-difluoro-5′-(7- trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile, a GABA α2/3 agonist". . p. 398 - 402. Retrieved 2012/12/22.