2-Cyanophenylboronic acid

Bezeichnung:2-Cyanophenylboronic acid

CAS-Nr138642-62-3

Englisch Name:2-Cyanophenylboronic acid

CBNumberCB4686341

SummenformelC7H6BNO2

Molgewicht146.94

MOL-Datei138642-62-3.mol

2-Cyanophenylboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	240 °C (dec.) (lit.)
Siedepunkt	376.4±44.0 °C(Predicted)
Dichte	1.25±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Soluble in methanol.
Aggregatzustand	Powder
pka	7.98±0.58(Predicted)
Farbe	Off-white to cream
InChI	InChI=1S/C7H6BNO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,10-11H
InChIKey	NPLZNDDFVCGRAG-UHFFFAOYSA-N
SMILES	B(C1=CC=CC=C1C#N)(O)O
CAS Datenbank	138642-62-3(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36/37/39-37/39-36
RIDADR	3439
WGK Germany	3
Hazard Note	Irritant
HS Code	29163990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

2-Cyanophenylboronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
off-white to cream powder
Verwenden
2-Cyanophenylboronic Acid is used in the synthesis of pyridine inhibitors of TAK1. Also participates in the discovery and synthesis of 1,2,4-triazoles as novel allosteric valosine containing protein (VCP) inhibitors. VCP is found highly abundant in various tumor types allowing for a potential target in cancer therapy.
Synthese

5419-55-6

7732-18-5

100-47-0

138642-62-3

Under nitrogen protection, 7.88 g (55.8 mmol) of 2,2,6,6-tetramethylpiperidine and 2.77 g (65.3 mmol) of lithium chloride (1.17:1 molar ratio to 2,2,6,6-tetramethylpiperidine) in THF were added to a 300 mL flask. A lithium 2,2,6,6-tetramethylpiperidine solution was prepared by slow dropwise addition of 24.2 g (58.2 mmol) of 15% n-butyllithium hexane solution at -10 °C. After cooling the reaction system to -50 °C, 10.93 g (58.2 mmol) of triisopropoxyborane and 4.98 g (48.3 mmol) of benzonitrile were added sequentially dropwise, and the reaction was maintained at this temperature for 3 h. HPLC analysis showed that the area percentage of 2-cyanobenzeneboronic acid in the reaction solution was 98.6%, and the by-product, 1 -phenyl-1 -(2,2,6,6-tetramethylpiperidin- 1-yl)methylimine had an area percentage of 1.38%. The reaction solution was poured into 38 mL of 3N HCl for hydrolysis and 150 mL of ethyl acetate was added for extraction to separate the aqueous phase. The organic phase was washed with 50 mL of 0.2N HCl and quantitatively analyzed by HPLC to confirm that the yield of 2-cyanophenylboronic acid was 95.0% and it contained 0.45% of 1-phenyl-(2,2,6,6-tetramethylpiperidin-1-yl)methylimine.
Einzelnachweise
[1] Patent: JP2015/160823, 2015, A. Location in patent: Paragraph 0053

2-Cyanophenylboronic acid Upstream-Materialien And Downstream Produkte

2-Cyanophenylboronic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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