2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1192548-08-5
• Molecular Formula: C13H18BFO2
• Molecular Weight: 236.094
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40682223
• Wikidata: Q82606530
• Mol file: 1192548-08-5.mol

Synonyms:1192548-08-5;2-(2-fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Fluoro-3-methylbenzeneboronic acid pinacol ester;2-Fluoro-3-methylphenylboronic acid, pinacol ester;2-fluoro-3-methylphenylboronic acid pinacol ester;MFCD18384075;(2-FLUORO-3-METHYLPHENYL)BORONIC ACID PINACOL ESTER;2-Fluoro-3-methylphenylboronic acid,pinacol ester;SCHEMBL13601620;DTXSID40682223;AKOS025293593;DS-10074;SY239846;CS-0041705;FT-0697397;EN300-3187727

Chemical Property of 2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Boiling Point: 308.5±35.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 2.43330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 236.1383881
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

98.5% ^*data from raw suppliers

2-Fluoro-3-methylphenylboronicAcid,PinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C(=CC=C2)C)F
• Uses: 2-Fluoro-3-methylphenylboronic Acid, Pinacol Ester acts as a reagent in the preparation of FASN inhibitors useful for the treatment of cancer and other diseases, fluorine-controlled carbon-hydrogen borylation of arenes catalyzed by phosphorus-silicon-nitrogen-pincer platinum complex.

Technology Process of 2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 5 articles about 2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 89.0%

2-(5-chloro-2-fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → C13H18BFO2 (1192548-08-5)

Guidance literature:

With potassium fluoride; palladium diacetate; In tetrahydrofuran; water; at 20 ℃; for 5h; Reagent/catalyst; Solvent; Temperature; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ol5028738

Reference yield: 50.0%

2-Fluorotoluene (95-52-3) + bis(pinacol)diborane (73183-34-3) → C13H18BFO2 (1192548-08-5)

Guidance literature:

2-Fluorotoluene; With sec.-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

bis(pinacol)diborane; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/anie.201801325

Reference yield:

5-chloro-2-fluorotoluene (452-66-4) + bis(pinacol)diborane (73183-34-3) → C13H18BFO2 (1192548-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Glovebox

2: palladium diacetate; potassium fluoride / tetrahydrofuran; water / 5 h / 20 °C / Inert atmosphere

With potassium fluoride; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; palladium diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; water;

DOI:10.1021/ol5028738

upstream raw materials:

5-chloro-2-fluorotoluene

bis(pinacol)diborane

2-Fluorotoluene

Refernces

• 1、 -. "METHODS FOR PRODUCING BORYLATED ARENES". . . Retrieved 2015/03/16.
• 2、 Jayasundara, Chathurika R. K.,Unold, Jason M.,Oppenheimer, Jossian,Smith, Milton R.,Maleczka, Robert E.. "A catalytic borylation/dehalogenation route to o -fluoro arylboronates". . p. 6072 - 6075. Retrieved 2015/01/09.