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2-Fluorophenylboronic acid

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CAS:1993-03-9
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CAS:1993-03-9
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CAS:1993-03-9
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  • CAS:1993-03-9
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2-Fluorophenylboronic acid Basic information
Product Name:2-Fluorophenylboronic acid
Synonyms:2-Fluorophenylboronic acid, May contain varying amounts of anhydride, 97%;2-Fluorophenylboroni;2-Fluorophenylboronic acid, 98% 1GR;Boronic acid, B-(2-fluorophenyl)-;BORONIC ACID, B-(2-FLUOROPHENYL)-; O-FLUORPHENYLBORSAEURE;;o-Fluorphenylborsaeure;o-fluoro-benzeneboronic acid;2-Flurorphenylboronic acid
CAS:1993-03-9
MF:C6H6BFO2
MW:139.92
EINECS:671-858-7
Product Categories:Boronate Ester;Potassium Trifluoroborate;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Substituted Boronic Acids;blocks;BoronicAcids;FluoroCompounds;Boronic Acid;Aryl;Fluorinated;Organoborons;Heterocyclic Compounds
Mol File:1993-03-9.mol
2-Fluorophenylboronic acid Structure
2-Fluorophenylboronic acid Chemical Properties
Melting point 101-110 °C (lit.)
Boiling point 267.8±42.0 °C(Predicted)
density 1.24±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility soluble in Methanol
form Crystalline Powder
pka8.32±0.58(Predicted)
color White to light yellow
BRN 3030413
InChIInChI=1S/C6H6BFO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H
InChIKeyQCSLIRFWJPOENV-UHFFFAOYSA-N
SMILESB(C1=CC=CC=C1F)(O)O
CAS DataBase Reference1993-03-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 36/37/38-22
Safety Statements 37/39-26-36/37/39-27-24/25
WGK Germany 3
HazardClass IRRITANT
HS Code 29319090
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
2-Fluorophenylboronic acid Usage And Synthesis
Chemical Propertieswhite to light yellow crystalline powder
Usessuzuki reaction
Uses2-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.
UsesUsed for the preparation of biologically active biphenyls and arylboron difluoride Lewis acids.
Synthesis
2-Bromofluorobenzene

1072-85-1

2-Fluorophenylboronic acid

1993-03-9

The general procedure for the synthesis of 2-fluorophenylboronic acid from o-bromofluorobenzene was as follows: 10.0 g (57.1 mmol) of 1-bromo-2-fluorobenzene and anhydrous tetrahydrofuran were added to a reaction flask and the mixture was subsequently cooled to -70 °C. At -70 °C, 44.2 ml (68.5 mmol) of 1.55 M n-butyllithium solution was slowly added dropwise to the reaction mixture. The temperature was maintained at -70 °C and stirring of the reaction mixture was continued for 1.5 hours. Subsequently, 21.5 g (114.2 mmol) of triisopropyl borate was added dropwise and the reaction temperature was gradually raised to room temperature and stirring was continued for 4 hours. Upon completion of the reaction, aqueous hydrochloric acid was added to the reaction mixture and extracted with dichloromethane. The organic phases were combined and the solvent was removed by distillation under reduced pressure to give the crude product of 2-fluorophenylboronic acid. The crude product was purified by column chromatography (eluent: hexane/acetone) to give 4.8 g (yield: 61%) of pure 2-fluorophenylboronic acid.

References[1] Patent: US2012/273770, 2012, A1. Location in patent: Page/Page column 24
[2] Patent: US2004/6076, 2004, A1. Location in patent: Page 15
[3] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
Tag:2-Fluorophenylboronic acid(1993-03-9) Related Product Information
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