| Identification | More | [Name]
1-Benzyl-1H-pyrazole-4-boronic acid pinacol ester | [CAS]
761446-45-1 | [Synonyms]
1-BENZYL-1H-PYRAZOLE-4-BORONIC ACID, PINACOL ESTER
1-BENZYL-4-1H-PYRAZOLEBORONIC ACID, PINACOL ESTER
1-BENZYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE
1-Benzyl-1H-pyrazol-4-ylboronic acid, pinacol ester
1-BENZYLPYRAZOLE-4-BORONIC ACID PINACOL ESTER, 95%
1-BENZYL-4-PYRAZOLEBORONIC ACID PINACOL ESTER
1-Benzyl-4-pyrazole boronic acid pinacol ester, 1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | [EINECS(EC#)]
671-685-7 | [Molecular Formula]
C16H23BN2O3 | [MDL Number]
MFCD03789252 | [Molecular Weight]
302.18 | [MOL File]
761446-45-1.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light yellow crystals or | [Melting point ]
86-90 °C(lit.) | [Boiling point ]
427.9±28.0 °C(Predicted) | [density ]
1.07±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
solid | [pka]
1.85±0.10(Predicted) | [color ]
white to yellow | [Water Solubility ]
Insoluble | [InChI]
1S/C16H21BN2O2/c1-15(2)16(3,4)21-17(20-15)14-10-18-19(12-14)11-13-8-6-5-7-9-13/h5-10,12H,11H2,1-4H3 | [InChIKey]
ZVPORPUUZXIPEF-UHFFFAOYSA-N | [SMILES]
CC1(C)OB(OC1(C)C)c2cnn(Cc3ccccc3)c2 | [CAS DataBase Reference]
761446-45-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
No | [HS Code ]
29331990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light yellow crystals or | [Uses]
1-Benzylpyrazole-4-boronic acid pinacol ester can be used:
- As a model compound in the study of the stability of boronate esters in different alcohols using the LCMS technique.
- As a substrate in the study of palladium-catalyzed methylation of heteroaryl boronate esters using iodomethane.
- As a substrate in the preparation of bromodifluoromethylthiolated arenes, applicable in the radiosynthesis of [18F]ArylSCF3 compounds.
| [Synthesis]
GENERAL STEPS: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (3.0 g, 15.5 mmol) was mixed with bromomethylbenzene (3.2 g, 18.7 mmol) in a solution of DMF (30 mL) containing K2CO3 (4.3 g, 31.2 mmol) and stirred at room temperature overnight. After completion of the reaction, the reaction mixture was diluted with EtOAc (50 mL) and H2O (50 mL), the organic layer was separated and washed with brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography using PE/EtOAc (5:1) as eluent to afford the target compound 1-benzyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (3.5 g, 12.3 mmol) as a light yellow solid in 79% yield.1H NMR (400 MHz. CDCl3): δ 7.81 (s, 1H), 7.66 (s, 1H), 7.37-7.29 (m, 3H), 7.24-7.22 (m, 2H), 5.30 (s, 2H), 1.29 (s, 12H). lcms (M + H) + 285. | [References]
[1] Patent: US2018/296543, 2018, A1. Location in patent: Paragraph 0573; 0574; 0600
[2] Patent: WO2015/95767, 2015, A1. Location in patent: Page/Page column 284; 285
[3] Patent: WO2016/124508, 2016, A1. Location in patent: Page/Page column 55
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1370 - 1387
[5] Patent: WO2014/60395, 2014, A1. Location in patent: Page/Page column 35 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Felongchem Co., Ltd.
|
| Telephone: |
021-68735616 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList12653/0_EN.htm |
| Company Name: |
T&W GROUP
|
| Telephone: |
021-61551611 13296011611 |
| Website: |
www.trustwe.com/ |
|