Pyridine-4-boronic acid

Bezeichnung:Pyridine-4-boronic acid

CAS-Nr1692-15-5

Englisch Name:Pyridine-4-boronic acid

CBNumberCB7220144

SummenformelC5H6BNO2

Molgewicht122.92

MOL-Datei1692-15-5.mol

Pyridine-4-boronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	>300 °C (lit.)
Siedepunkt	308.8±34.0 °C(Predicted)
Dichte	1.22±0.1 g/cm3(Predicted)
storage temp.	-20°C
Löslichkeit	Aqueous Acid (Slightly), Water (Slightly)
Aggregatzustand	Solid
pka	7.59±0.10(Predicted)
Farbe	White to Off-White
BRN	471944
InChI	InChI=1S/C5H6BNO2/c8-6(9)5-1-3-7-4-2-5/h1-4,8-9H
InChIKey	QLULGIRFKAWHOJ-UHFFFAOYSA-N
SMILES	C1=NC=CC(B(O)O)=C1
CAS Datenbank	1692-15-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi,C,F
R-Sätze:	36/37/38-22-34-11
S-Sätze:	22-24/25-36/37/39-26-45-16
WGK Germany	3
Hazard Note	Irritant
HazardClass	IRRITANT, KEEP COLD
HS Code	29339900
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

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

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
R34:Verursacht Verätzungen.
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S16:Von Zündquellen fernhalten - Nicht rauchen.
Beschreibung
Pyridine-4-boronic acid is a kind of boronic acid derivative. It is useful building blocks in crystal engineering. It can also be used as a catalyst to act as a dehydrative condensation agent to synthesize amides using carboxylic acid and amines as raw materials. Its derivative, polystyrene-bound 4-pyridineboronic acid, is a useful catalyst for amidation reaction and esterification of alpha-hydrocarboxylic acids.
Chemische Eigenschaften
light orange granular powder
Verwenden
Boronic acid derivatives and their binding affinities with diols.
Verwenden
Reagent used for
- Palladium-catalyzed Suzuki-Miyaura coupling reactions
- Ligand-free palladium-catalyzed Suzuki coupling reaction under microwave irradation
Reagent used in Preparation of
- HIV-1 protease inhibitors
- Potential cancer threapeutics, such as PDK1 and protein kinase CK2 inhibitors
Verwenden
suzuki reaction
Synthese

1120-87-2

121-43-7

7732-18-5

1692-15-5

Under argon protection, 4-bromopyridine (1.5 g, 10 mmol) was placed in a 200 mL Schlenk flask and 40 mL of anhydrous deoxytetrahydrofuran was added. After cooling the reaction mixture to -78 °C, 5 mL (2.2 M, 11 mmol) of n-butyllithium solution was slowly added dropwise and the reaction was maintained at this temperature for 1 hour. Subsequently, 4 mL of trimethyl borate was added and the reaction continued at -78 °C for 1 hour. Upon completion of the reaction, the mixture was slowly warmed to room temperature and stirred overnight. The reaction was quenched with 2 mol/L hydrochloric acid solution and purified by recrystallization from hexane to give pyridine-4-boronic acid hydrochloride (0.8 g, 65% yield).
Einzelnachweise
http://www.wako-chem.co.jp/english/labchem/product/Org/pyridineboronic/
José J. CamposGaxiola et al. "Pyridineboronic Acids as Useful Building Blocks in Combination with Perchloroplatinate(II) and -(IV) Salts: 1D, 2D, and 3D Hydrogen-Bonded Networks Containing X-H•••Cl2Pt− (X = C, N+), B(OH)2•••Cl2Pt−, and B(OH)2•••(HO)2B Synthons." Crystal Growth & Design 10.7(2010).
Kara, H., A. G. Orpen, and T. J. Podesta. "Pyridine boronic acids as building blocks in crystal engineering." Acta Crystallographica 61.Suppl (2001): C357.

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

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