Pyridine-4-boronic acid Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

308.8±34.0 °C(Predicted)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Aqueous Acid (Slightly), Water (Slightly)

form 

Solid

pka

7.59±0.10(Predicted)

color 

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 DataBase Reference

1692-15-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,C,F

Risk Statements 

36/37/38-22-34-11

Safety Statements 

22-24/25-36/37/39-26-45-16

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Pyridine-4-boronic acid Usage And Synthesis

Uses

Pyridine-4-boronic acid can be used as a candidate for Suzuki-Miyaura coupling reaction. Especially, as a N-containing building blocks, pyridine-4-boronic acid was employed to construct some heterocyclic compounds with superior biological activities.

Description

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.

Chemical Properties

light orange granular powder

Uses

suzuki reaction

Uses

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

Uses

Boronic acid derivatives and their binding affinities with diols.

Synthesis

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).

References

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(1692-15-5)Related Product Information

• 4-Pyridineboronic acid pinacol ester
• 4-Methylpyridine
• Chromium picolinate
• Zinc borate
• 3-Pyridylboronic acid
• Sulfasalazine
• Methyl propyl carbonate
• (+/-)-NICOTINE
• 3-Pyridylacetic acid hydrochloride
• 2-Pyridinecarboxaldehyde
• Pyridine-2-carbonyl chloride hydrochloride
• 2-(Hydroxymethyl)pyridine
• ISONICOTINOYL CHLORIDE HYDROCHLORIDE
• 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• Boric acid
• 2-PYRIDINEMETHANOL HYDROCHLORIDE
• Pyridine hydrochloride
• Pyridine hydrobromide