Dibenzofuran-4-boronic acid

Bezeichnung:Dibenzofuran-4-boronic acid

CAS-Nr100124-06-9

Englisch Name:Dibenzofuran-4-boronic acid

CBNumberCB1671054

SummenformelC12H9BO3

Molgewicht212.01

MOL-Datei100124-06-9.mol

Dibenzofuran-4-boronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	286-291 °C (lit.)
Siedepunkt	438.5±37.0 °C(Predicted)
Dichte	1.34±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
pka	8.04±0.30(Predicted)
Aggregatzustand	powder
Farbe	white to off-white
BRN	1645426
InChIKey	ZXHUJRZYLRVVNP-UHFFFAOYSA-N
CAS Datenbank	100124-06-9(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	37/39-26-24/25
WGK Germany	3
TSCA	No
HazardClass	IRRITANT
HS Code	29321900

Gefahreninformationscode (GHS)

Dibenzofuran-4-boronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Dibenzofuran-4-boronic acid (DBFBA) is a boronic acid that has been used as a cross-coupling agent in the Suzuki coupling reaction. It has been shown to have low efficiency, but advances in this area have been made through the use of methanol extraction and photophysical properties. DBFBA is often coupled with imidazole derivatives to form anti-inflammatory compounds. The bond cleavage and hydrogen bonding properties of DBFBA make it a good target for drug synthesis.
Chemische Eigenschaften
off-white to beige powder
Verwenden
Dibenzofuran-4-boronic acid is a water-soluble boronic acid, and the boronic acid molecule is a very useful functional group for the preparation of glycosensors. Water-soluble boronic acids that change their fluorescence properties upon binding to sugars are particularly useful as reporter units for carbohydrate fluorescence sensors. Dibenzofuran-4-boronic acid displays distinctive fluorescence changes at three wavelengths when bound to sugars under near-physiological conditions^[1].
Synthese
In a 300 ml three-necked flask, 7.2 g of 4-bromodibenzofuran was dissolved in -78° C. anhydrous tetrahydrofuran (THF) under an argon atmosphere. Then, 20 ml of an n-butyl lithium-n-hexane solution (1.6 M, 1.1 eq) was added and stirred for 1 hour. 4.23 ml (1.3 eq) of trimethoxyborane (B(OMe)3) was added and stirred for 2 hours, and the temperature of the reaction system was increased to room temperature. 200 ml of 1 N hydrochloric acid was added into the reactant and stirred for 3 hours. An organic layer was separated, and solvents were distilled off. In the crude product thus obtained, hexane was added. Precipitated product was filtered to obtain 4.94 g of dibenzofuran-4-boronic acid as a white solid (yield 80%).
Einzelnachweise
[1] JUNFENG WANG Binghe W Shan Jin. A new boronic acid fluorescent reporter that changes emission intensities at three wavelengths upon sugar binding[J]. Tetrahedron Letters, 2005. DOI:10.1016/j.tetlet.2005.08.053.

Dibenzofuran-4-boronic acid Upstream-Materialien And Downstream Produkte

Dibenzofuran-4-boronic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

100124-06-9, Dibenzofuran-4-boronic acid Verwandte Suche:

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