|
|
| | 5-Pyrimidinylboronic acid Basic information |
| | 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) |
| Hazard Codes | Xi,Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 22-26-36/37/39-36 | | WGK Germany | WGK 3 | | HazardClass | IRRITANT | | HS Code | 29335990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| | 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 Preparation Products And Raw materials |
|