| Identification | Back Directory | [Name]
1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE | [CAS]
827614-66-4 | [Synonyms]
827614-66-4
1-Isobutyl-4-(4
2-dioxaborolan-2-yl)-1H-pyrazole
1-ISOBUTYL-PYRAZOLE-4-BORONIC ACID PINACOL ESTER
1-Isobutylpyrazole-4-boronic acid pinacol ester 95%
1-ISOBUTYL-1H-PYRAZOLE-4-BORONIC ACID, PINACOL ESTER
1-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
N-Isobutyltetrahydrothiophene-3-amine-1,1-dioxidehydrochloride
1-(2-methylpropyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1...
1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE
1-(2-methylpropyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
1-(2-methylpropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole
1-(2-Methylpropyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
1H-Pyrazole, 1-(2-Methylpropyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
1-Isobutyl-pyrazole-4-boronic acid pinacol ester, 1-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | [Molecular Formula]
C13H23BN2O2 | [MDL Number]
MFCD05663857 | [MOL File]
827614-66-4.mol | [Molecular Weight]
250.14 |
| Chemical Properties | Back Directory | [Boiling point ]
248-249 °C(lit.)
| [density ]
1.003 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4740(lit.)
| [Fp ]
118 °F
| [storage temp. ]
2-8°C | [form ]
Liquid | [pka]
2.07±0.10(Predicted) | [color ]
Colorless to yellow | [InChI]
1S/C13H23BN2O2/c1-10(2)8-16-9-11(7-15-16)14-17-12(3,4)13(5,6)18-14/h7,9-10H,8H2,1-6H3 | [InChIKey]
YMEBZRNYQBODKB-UHFFFAOYSA-N | [SMILES]
CC(C)Cn1cc(cn1)B2OC(C)(C)C(C)(C)O2 | [CAS DataBase Reference]
827614-66-4 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
10-36/38 | [Safety Statements ]
16-26-36 | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [HazardClass ]
3 | [HS Code ]
2933199090 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Uses]
1-Isobutylpyrazole-4-boronic acid pinacol ester can be used:
- In the synthesis of 7-azaindole derivatives as potent PDK1 inhibitors.
- As a reactant in the synthesis of imidazo[1,2-a]pyrazine derivatives as potent phosphodiesterase 10A inhibitors.
- To prepare 2-substituted-3-aroyl-benzo[b]furan derivatives.
| [Uses]
1-Isobutylpyrazole-4-boronic acid, pinacol ester | [Synthesis]
To 4-pyrazoleboronic acid pinacol ester (1 g, 5.15 mmol, 1.00 eq.) and isobutyl bromide (1.05 g, 7.66 mmol, 1.49 eq.) in ethyl acetate (60 mL), Cs2CO3 (3.36 g, 10.31 mmol, 2.00 eq.) was added. The reaction mixture was stirred at 80 °C for 4 hours. After completion of the reaction, it was cooled to room temperature and filtered to remove insoluble solids. The filtrate was diluted with ethyl acetate (30 mL) and subsequently washed with brine (40 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum to afford 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.14 g, 88% yield) as a colorless oil.1H-NMR (300 MHz, CDCl3): δ 7.78 (s, 1H), 7.65 (s, 1H), and 3.91 (d, J=7.2Hz, 2H), 2.24-2.19 (m, 1H), 1.32 (s, 12H), 0.90 (d, J=7.2Hz, 6H) ppm. lcms (method D, ESI): rt=1.51min, m/z=251.0[M+H]+. | [References]
[1] Patent: US2014/288105, 2014, A1. Location in patent: Paragraph 0216-0217
[2] Patent: EP3042907, 2016, A1. Location in patent: Paragraph 0277; 0278
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 24, p. 7934 - 7937 |
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