4-Biphenylboronic acid

Bezeichnung:4-Biphenylboronic acid

CAS-Nr5122-94-1

Englisch Name:4-Biphenylboronic acid

CBNumberCB8127772

SummenformelC12H11BO2

Molgewicht198.03

MOL-Datei5122-94-1.mol

4-Biphenylboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	232-245 °C (lit.)
Siedepunkt	385.5±35.0 °C(Predicted)
Dichte	1.18±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	soluble in Acetone,Methanol
Aggregatzustand	Powder
pka	8.61±0.10(Predicted)
Farbe	White
Wasserlöslichkeit	Insoluble in water.
BRN	2937410
InChI	InChI=1S/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H
InChIKey	XPEIJWZLPWNNOK-UHFFFAOYSA-N
SMILES	B(C1=CC=C(C2=CC=CC=C2)C=C1)(O)O
CAS Datenbank	5122-94-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-20/21/22
S-Sätze:	26-37/39-36-24/25
WGK Germany	3
TSCA	No
HazardClass	IRRITANT
HS Code	29310095
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

4-Biphenylboronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
Solid
Verwenden
Used in Suzuki reactions and as intermediates of liquid crystals.
Verwenden
suzuki reaction: Suzuki coupling of 2-(4-bromophenyl)thiophene with phenylboronic acid and 4-biphenylboronic acid are used for the preparation of 4-(2-thieny)biphenyl and 4-(2-thienyl)-1,1':4,1''-biphenyl respectively. Coupling of two equivalents of 4-(2-thienyl)phenylboronic acid with 1,4-diiodobenzene gives 4,4''-bis(2-thienyl)-1,1':4,1''-terphenyl and with 2,5-diiodothiophene, 2,5-bis[4-(2-thienyl)-phenyl]-thiophene is obtained.
Synthese

92-66-0

5122-94-1

The general procedure for the synthesis of 4-biphenylboronic acid from 4-bromobiphenyl was as follows: 4-bromobiphenyl (30 g, 0.12 mol) was added to a single-neck flask and the reaction was carried out under argon protection. Tetrahydrofuran (THF) (500 mL) was added and stirred at -78 °C for 10 min. Slowly n-butyllithium (2.5 M in hexane) (77 mL, 0.19 mol) was added and the mixture was stirred at -78 °C for 1 hour. Subsequently, dimethyl borate (21.9 mL, 0.19 mol) was added at -78 °C and stirring was continued at -78 °C for 30 min, then brought to room temperature and stirred for 4 hours. After completion of the reaction, extraction was carried out with distilled water and ethyl acetate (EA) and the organic layer was dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed using a rotary evaporator. Finally, pure 4-biphenylboronic acid (21 g, 84% yield) was isolated by column chromatography using hexane and ethyl acetate (EA) as eluents.
Einzelnachweise
[1] Patent: WO2011/105700, 2011, A1. Location in patent: Page/Page column 18; 19; 21; 22
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 9, p. 1404 - 1408
[3] Tetrahedron, 2007, vol. 63, # 20, p. 4297 - 4303
[4] Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1013 - 1030
[5] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571

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