1-Methyl-4-pyrazole boronic acid pinacol ester
Synonym(s):1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;1-Methyl-4-pyrazoleboronic acid pinacol ester;2-(1-Methylpyrazol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-methylpyrazole
- CAS NO.:761446-44-0
- Empirical Formula: C10H17BN2O2
- Molecular Weight: 208.07
- MDL number: MFCD03789259
- EINECS: 616-293-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-28 13:16:12
What is 1-Methyl-4-pyrazole boronic acid pinacol ester?
Chemical properties
White to light yellow crystal powde
The Uses of 1-Methyl-4-pyrazole boronic acid pinacol ester
1-Methyl-4-pyrazole boronic acid pinacol ester is a reagent used for:Suzuki-Miyaura cross-coupling reactions1,2,3• ;Transesterification reactions4Reagent used for preparation of• ;Aminothiazoles as γ-secretase modulators5• ;Amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy6• ;Pyridine derivatives as TGF-β1 and activin A signalling inhibitors7• ;MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer8.
The Uses of 1-Methyl-4-pyrazole boronic acid pinacol ester
suzuki reaction
The Uses of 1-Methyl-4-pyrazole boronic acid pinacol ester
1-Methyl-4-pyrazole boronic acid pinacol ester is a reagent used for Suzuki-Miyaura cross-coupling reactions, transesterification reactions. It is involved in several reactions as a reagent for the preparation of aminothiazoles as γ-secretase modulators,amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy, pyridine derivatives as TGF-β1 and active A signaling inhibitors and MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer.
Synthesis
To the solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.40 g, 2.06 mmol) in THF (10 mL) was added NaH (0.1.00 g, 4.12 mmol) followed by methyl iodide (0.25 mL, 4.12 mmol) at 0° C and the reaction mixture was stirred at ambient temperature for 4 hr. The reaction was quenched with saturated NH4Cl solution (20 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate, and distilled under reduced pressure to obtain 1-Methyl-4-pyrazole boronic acid pinacol ester.
Properties of 1-Methyl-4-pyrazole boronic acid pinacol ester
Melting point: | 59-64 °C(lit.) |
Boiling point: | 308.3±15.0 °C(Predicted) |
Density | 1.05±0.1 g/cm3(Predicted) |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | Chloroform (slightly), Methanol (Slightly) |
form | Crystals |
pka | 2.09±0.10(Predicted) |
color | Off-white to yellow |
Water Solubility | Slightly soluble in water. |
InChI | InChI=1S/C10H17BN2O2/c1-9(2)10(3,4)15-11(14-9)8-6-12-13(5)7-8/h6-7H,1-5H3 |
CAS DataBase Reference | 761446-44-0(CAS DataBase Reference) |
Safety information for 1-Methyl-4-pyrazole boronic acid pinacol ester
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for 1-Methyl-4-pyrazole boronic acid pinacol ester
InChIKey | UCNGGGYMLHAMJG-UHFFFAOYSA-N |
SMILES | N1(C)C=C(B2OC(C)(C)C(C)(C)O2)C=N1 |
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