2,4-Difluorophenylboronic acid

Base Information

• Chemical Name: 2,4-Difluorophenylboronic acid
• CAS No.: 144025-03-6
• Molecular Formula: C6H5BF2O2
• Molecular Weight: 157.912
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID50370225
• Nikkaji Number: J1.349.724I
• Wikidata: Q72463762
• Mol file: 144025-03-6.mol

Synonyms:2,4-Difluorophenylboronic acid;144025-03-6;(2,4-difluorophenyl)boronic acid;2,4-Difluorobenzeneboronic Acid;MFCD01318998;Boronic acid, (2,4-difluorophenyl)-;2,4-Difluorophenylboronicacid;(2,4-Difluorophenyl)Boranediol;2,4-Difluorophenyl-boronic acid;2,4-Difluorophenyl boronic acid;BORONIC ACID, B-(2,4-DIFLUOROPHENYL)-;SCHEMBL39406;2,4-diflurophenylboronic acid;AKOS BRN-0089;2.4-difluorophenylboronic acid;2,4 difluorophenyl boronic acid;2,4-difluoro-phenylboronic acid;DTXSID50370225;2,4-di-fluoro-phenylboronic acid;2,4-Difluoro-phenyl-boronic acid;QQLRSCZSKQTFGY-UHFFFAOYSA-N;2, 4-difluorobenzene boronic acid;2,4-difluoro-benzene-boronic acid;(2,4-difluorophenyl) boronic acid;BCP22755;CS-D1002;dihydroxy(2,4-difluorophenyl)borane;STK503723;AKOS000264711;AB08813;AC-5375;BCP9000261;GS-6461;OL10075;PB40679;2,4-DIFLUOROBENZENE BORONIC ACID;NCGC00249465-01;BP-11370;SY005771;AM20060167;D3391;FT-0610085;EN300-117676;J-507219;Z381540906;2,4-Fluorobenzene boronic acid

Chemical Property of 2,4-Difluorophenylboronic acid

Chemical Property:

• Appearance/Colour: off-white to light beige or yellow powder
• Vapor Pressure: 1.14mmHg at 25°C
• Melting Point: 247-250 ºC
• Boiling Point: 251 ºC at 760 mmHg
• PKA: 8.47±0.58(Predicted)
• Flash Point: 105.6 ºC
• PSA: 40.46000
• Density: 1.35 g/cm³
• LogP: -0.35540
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 158.0350659
• Heavy Atom Count: 11
• Complexity: 134

Purity/Quality:

99% ^*data from raw suppliers

2,4-Difluorophenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=C(C=C1)F)F)(O)O
• Uses: suzuki reaction 2,4-Difluorophenylboronic Acid is used as a reagent in suzuki-miyaura coupling reactions such as in the synthesis of enantiomerically pure 3,3''-bis-arylated BINOL derivatives. Also used in the synthesis of highly efficient phospherescent iridium (III) complexes which are used for light-emiiting diodes.

Technology Process of 2,4-Difluorophenylboronic acid

There total 7 articles about 2,4-Difluorophenylboronic 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: 84.3%

Trimethyl borate (121-43-7,63156-11-6) + (2,4-difluorophenyl)magnesium bromide (144025-04-7) → 2,4-difluorophenylboronic acid (144025-03-6)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; water;

Reference yield: 77.0%

2,4-difluorobromobenzene (348-57-2) + Trimethyl borate (121-43-7,63156-11-6) → 2,4-difluorophenylboronic acid (144025-03-6)

Guidance literature:

With n-butyllithium; In diethyl ether; hexane; n-BuLi (2.5 M, hexane) was added to C6F2BrH3 in Et2O at -70 °C, 1.5 equiv. of cold soln. of B(OMe)3 was added in Et2O, stirring at -60 °C for 1 h, mixt. was allowed to warm to 15 °C within 1 h; poured into 5 % HCl, org. layer was sepd., aq. layer was twice extd. with ether, extracts were combined, dried with MgSO4, evapn., solid was stored over water at 15 °C for 1 month;

DOI:10.1002/1521-3749(200213)628:13<2827::AID-ZAAC2827>3.0.CO;2-N

Reference yield:

2-methoxy-ethanol (109-86-4,95507-80-5) → 2,4-difluorophenylboronic acid (144025-03-6)

Guidance literature:

With sodium carbonate; In water; acetylacetone;

upstream raw materials:

Trimethyl borate

(2,4-difluorophenyl)magnesium bromide

C₆H₃BF₅^(1-)

2,4-difluorobromobenzene

Downstream raw materials:

2-(3-nitro-4-methoxyphenyl)-5-(2,4-difluorophenyl)benzoxazole

C₁₁H₆F₂OS

1-benzyl-4,5-dibromo-2-(2,4-difluoro-phenyl)-imidazole

Refernces

• 1、 -. "A normal-temperature process for preparing 2, 4 - difluorobenzene boric acid (by machine translation)". Paragraph 0017-0024. . Retrieved 2018/04/01.
• 2、 -. "Synthetic method of organometallic iridium compound". Page/Page column 2-3. . Retrieved 2012/12/14.