2-Fluorophenylboronic acid

Base Information

• Chemical Name: 2-Fluorophenylboronic acid
• CAS No.: 1993-03-9
• Molecular Formula: C6H6BFO2
• Molecular Weight: 139.922
• Hs Code.: 29319090
• European Community (EC) Number: 671-858-7
• DSSTox Substance ID: DTXSID30941836
• Nikkaji Number: J1.088.588D
• Wikidata: Q72475738
• ChEMBL ID: CHEMBL505047
• Mol file: 1993-03-9.mol

Synonyms:2-Fluorophenylboronic acid;1993-03-9;(2-fluorophenyl)boronic acid;2-Fluorobenzeneboronic Acid;(2-fluorophenyl)boranediol;2-Fluorophenylboronicacid;o-fluorophenylboronic acid;MFCD00674013;BORONIC ACID, (2-FLUOROPHENYL)-;2-fluorophenyl boronic acid;34-03-7;Boronic acid, B-(2-fluorophenyl)-;O-FLUORO-BENZENEBORONIC ACID;o-fluorobenzeneboronic acid;D0U7RS;(2-fluorophenyl)boronicacid;2-fluoro phenylboronic acid;2-fluoro-phenylboronic acid;2-Fluorophenyl-boronic acid;2-fluoro benzeneboronic acid;2-fluorobenzene boronic acid;2-fluorobenzene-boronic acid;2-fluoro -phenylboronic acid;2-fluoro phenyl boronic acid;2-fluoro-phenyl boronic acid;2-fluoro-phenyl-boronic acid;SCHEMBL115327;(2-fluorophenyl) boronic acid;(2-Fluorophenyl)boronato(2-);CHEMBL505047;dihydroxy(2-fluorophenyl)borane;BDBM26135;QCSLIRFWJPOENV-UHFFFAOYSA-;DTXSID30941836;QCSLIRFWJPOENV-UHFFFAOYSA-N;STK503728;AKOS000265043;AB06918;AC-5348;AS-2595;CS-W001240;OL10073;NCGC00249458-01;BP-13022;PD180468;SY001055;AM20060159;F0407;FT-0612449;FT-0645760;FT-0686426;EN300-88718;4-Piperidinamine,1-methyl-,hydrochloride(1:2);A814085;J-500812;Z381540942;InChI=1/C6H6BFO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H

Chemical Property of 2-Fluorophenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 0.00395mmHg at 25°C
• Melting Point: 101-110 °C(lit.)
• Refractive Index: 1.508
• Boiling Point: 267.8 °C at 760 mmHg
• PKA: 8.32±0.58(Predicted)
• Flash Point: 115.8 °C
• PSA: 40.46000
• Density: 1.24 g/cm³
• LogP: -0.49450
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 140.0444878
• Heavy Atom Count: 10
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

2-Fluorophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36/37/39-27-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1F)(O)O
• Uses: suzuki reaction 2-Fluorophenylboronic Acid, is used in Rh-catalyzed enantioselective addition reactions, and Rhodium and Palladium-catalyzed substitution reactions. It can also be used in the preparation of phenylboronic catechol esters as promising anion receptors for polymer electrolytes. Used for the preparation of biologically active biphenyls and arylboron difluoride Lewis acids.

Technology Process of 2-Fluorophenylboronic acid

There total 14 articles about 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: 97.0%

o-fluorobromobenzene (1072-85-1) + Trimethyl borate (121-43-7,63156-11-6) → o-fluorophenylboronic acid (1993-03-9)

Guidance literature:

o-fluorobromobenzene; 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: 93.0%

fluorobenzene (462-06-6) + Triisopropyl borate (5419-55-6) → o-fluorophenylboronic acid (1993-03-9)

Guidance literature:

With hydrogenchloride; sec.-butyllithium; In tetrahydrofuran; BuLi add. to org. compd. soln. at -78°C (N2)=, stirring 2 h at same temp., B-compd. addn. over 5 min. mixt. stirring (-78°C/2 h, room temp./overnight, N2), acidifying (HCl), H2O addn., extn. (Et2O), extracts shaking (3 M HCl, brine); drying (Na2SO4), solvent evapn. (water bath, 35°C), air drying overnight at room temp., stirring with ice-cold pentane (washings discarding), air drying overnight;

Reference yield: 85.0%

o-fluorobromobenzene (1072-85-1) + Triisopropyl borate (5419-55-6) → o-fluorophenylboronic acid (1993-03-9)

Guidance literature:

o-fluorobromobenzene; With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 0.5h; Inert atmosphere; Autoclave; Large scale;

Triisopropyl borate; In tetrahydrofuran; at -70 ℃; Large scale;

upstream raw materials:

1-Fluoro-2-iodobenzene

o-fluorobromobenzene

n-butyllithium

Triisopropyl borate

Downstream raw materials:

2,2-dimethyl-N-(4-(2-fluorophenyl)-3-pyridyl)propanamide

8-methoxy-5-nitro-4-(2'-fluorophenyl)quinoline

2,2'-difluorobiphenyl

(R)-3-(2-fluorophenyl)cyclohexan-1-one

Refernces

• 1、 Smith, Michael J.,Lawler, Michael J.,Kopp, Nathaniel,McLeod, Douglas D.,Davulcu, Akin H.,Lin, Dong,Katipally, Kishta,Sfouggatakis, Chris. "Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure". . p. 1859 - 1863. Retrieved 2017/11/24.
• 2、 Akgun, Burcin,Hall, Dennis G.. "Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation". supporting information. p. 3909 - 3913. Retrieved 2016/03/19.