5-Pyrimidinylboronic acid Chemical Properties

Melting point:

110-114 °C

Boiling point:

334.7±34.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Soluble in Ether, MeOH, DMSO, THF.

form 

powder to crystal

pka

5.23±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C4H5BN2O2/c8-5(9)4-1-6-3-7-2-4/h1-3,8-9H

InChIKey

HZFPPBMKGYINDF-UHFFFAOYSA-N

SMILES

B(C1=CN=CN=C1)(O)O

CAS DataBase Reference

109299-78-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39-36

HazardClass 

IRRITANT

HS Code 

29335990

5-Pyrimidinylboronic acid Usage And Synthesis

Chemical Properties

Off-white powder

Uses

suzuki reaction

Uses

5-Pyrimidylboronic Acid, is one of the new heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions.

Synthesis

General procedure for the synthesis of 5-pyrimidinylboronic acid from 5-bromopyrimidine: BuLi (3.02 mL, 2M hexane solution, 7.55 mmol) was slowly added dropwise to a stirring anhydrous toluene (16 mL) and anhydrous THF (4 mL) in a mixed solution of 5-bromopyrimidine (1 g, 6.29 mmol) and triisopropyl borate (1.46 mL, 7.55 mmol), under nitrogen protection. mL) in a mixed solution at a reaction temperature of -70 °C. The reaction mixture was continuously stirred at -70 °C for 30 min and then removed from the cold bath. When the internal temperature rose to -20 °C, the reaction was quenched by dropwise addition of 2M HCl (10 mL). Phase separation was carried out after gradually warming the mixture to room temperature. The aqueous phase was adjusted to pH 5.5 with 2M KOH and extracted with THF (3 x 25 mL). The organic phases were combined, dried with MgSO4, filtered and concentrated under reduced pressure to give a colorless solid. The solid was slurried in acetonitrile (2 mL), collected by filtration and dried over a sintered mass to give the final target product 5-pyrimidinylboronic acid as a bright white solid (340 mg, 44% yield).8H (MeOD; 250 MHz) 8.98 (2H, s), 9.14 (1H, s).

References

[1] Synthetic Communications, 2003, vol. 33, # 5, p. 795 - 800
[2] Organic and Biomolecular Chemistry, 2004, vol. 2, # 6, p. 852 - 857
[3] Patent: WO2005/103019, 2005, A1. Location in patent: Page/Page column 16
[4] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[5] Patent: US2006/111394, 2006, A1. Location in patent: Page/Page column 17

5-Pyrimidinylboronic acid(109299-78-7)Related Product Information

• Pyrimidine-5-boronic acid pinacol ester
• Ethyl 2-(Chlorosulfonyl)acetate
• Fluoroboric acid
• Pyrimidine
• Zinc borate
• Folic acid
• Boric acid
• Sulfadiazine
• Citric acid
• Ascoric Acid
• 4-BENZYLOXY-2-CHLOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER
• 2-Aminopyrimidine-5-boronic Acid Pinacol Ester
• 2,4-DI(TERT-BUTOXY)PYRIMIDIN-5-YLBORONIC ACID HYDRATE
• N-Phenyldiethanolamine 2-pyridylboronate
• 2,4-DICHLORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)PYRIMIDINE
• 2,4-BIS(BENZYLOXY)PYRIMIDINE-5-BORONIC ACID
• 2-Methoxypyrimidine-5-boronic acid
• 2,4-Dimethoxyprimidine-5-boronic acid