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| | 1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE Basic information |
| Product Name: | 1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE | | Synonyms: | 1-Isobutylpyrazole-4-boronic acid pinacol ester 95%;1-(2-methylpropyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);1-ISOBUTYL-1H-PYRAZOLE-4-BORONIC ACID, PINACOL ESTER;1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE;1-ISOBUTYL-PYRAZOLE-4-BORONIC ACID PINACOL ESTER;1-Isobutyl-4-(4;2-dioxaborolan-2-yl)-1H-pyrazole | | CAS: | 827614-66-4 | | MF: | C13H23BN2O2 | | MW: | 250.14 | | EINECS: | | | Product Categories: | Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronate Esters;Organometallic Reagents | | Mol File: | 827614-66-4.mol |  |
| | 1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE Chemical Properties |
| 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 |
| 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 |
| | 1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE Usage And Synthesis |
| Uses | 1-Isobutylpyrazole-4-boronic acid, pinacol ester | | 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.
| | 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 |
| | 1-ISOBUTYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE Preparation Products And Raw materials |
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