Quinoline-5-boronic acid

Bezeichnung:Quinoline-5-boronic acid

CAS-Nr355386-94-6

Englisch Name:Quinoline-5-boronic acid

CBNumberCB9704024

SummenformelC9H8BNO2

Molgewicht172.98

MOL-Datei355386-94-6.mol

Quinoline-5-boronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	144-148°C
Siedepunkt	400.3±37.0 °C(Predicted)
Dichte	1.28±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	powder to crystal
pka	7.46±0.30(Predicted)
Farbe	White to Light yellow to Light orange
InChI	InChI=1S/C9H8BNO2/c12-10(13)8-4-1-5-9-7(8)3-2-6-11-9/h1-6,12-13H
InChIKey	NWIJBOCPTGHGIK-UHFFFAOYSA-N
SMILES	B(C1=CC=CC2N=CC=CC1=2)(O)O
CAS Datenbank	355386-94-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-36/38
S-Sätze:	26-36-37/39-37
HazardClass	IRRITANT
HS Code	29334900

Gefahreninformationscode (GHS)

Quinoline-5-boronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R36/38:Reizt die Augen und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Verwenden
Quinoline-5-boronic acid is a fluorescent reporter compound that exhibits significant fluorescence property changes via a pKa-switching mechanism upon binding diols and carbohydrates in aqueous solutions at physiological pH[2]. Quinoline-5-boronic acid is used for monitoring sugars across a wide pH range, differentiating D-fructose from inulin, and functioning as a fluorescent probe for diols[2][3]. Quinoline-5-boronic acid is applied in fluorometric determination methods by combining with a phosphate buffer at neutral pH for selective D-fructose detection[3].
Synthese

4964-71-0

5419-55-6

355386-94-6

In a 100 mL three-necked flask, 5-bromoquinoline (10 mmol, 2.08 g) and anhydrous THF (50 mL) were added and n-butyllithium (11 mmol, 1.6 M, 6.88 mL) was added slowly and dropwise at -78 °C under nitrogen protection. After keeping the reaction at -78 °C for 2 h, a THF solution (5 mL) of triisopropyl borate (15 mmol, 3.03 g) was added slowly dropwise. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was monitored by TLC to confirm the disappearance of the feedstock, then the reaction was quenched with 20% dilute hydrochloric acid (20 mL) and stirred at room temperature for 3 hours. Subsequently, the reaction mixture was extracted with ethyl acetate (50 mL x 3), and the organic phases were combined, washed with saturated brine (100 mL x 3) and dried with anhydrous sodium sulfate. After concentrating the organic phase, it was purified by column chromatography to afford quinoline-5-boronic acid (7.6 mmol, 1.31 g, 76% yield).
Einzelnachweise
[1] Patent: CN107814795, 2018, A. Location in patent: Paragraph 0014; 0016
[2]Yang, W., Lin, L., & Wang, B. (2005). A new type of boronic acid fluorescent reporter compound for sugar recognition. Tetrahedron Letters, 46(46), 7981–7984. https://doi.org/10.1016/j.tetlet.2005.09.074
[3]Rikita, T., Egawa, Y., & Seki, T. (2012). Fluorometric determination of inulin using 5-quinolineboronic acid and inulinase. Analytical Biochemistry, 426(1), 24–26. https://doi.org/10.1016/j.ab.2012.03.029

Quinoline-5-boronic acid Upstream-Materialien And Downstream Produkte

Quinoline-5-boronic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

355386-94-6, Quinoline-5-boronic acid Verwandte Suche:

Send Inquriy