1-Methyl-4-pyrazole boronic acid pinacol ester CAS 761446-44-0

Introduction：Basic information about 1-Methyl-4-pyrazole boronic acid pinacol ester CAS 761446-44-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

1-Methyl-4-pyrazole boronic acid pinacol ester Basic information

• Product Name: 1-Methyl-4-pyrazole boronic acid pinacol ester
• Synonyms: 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-;1-METHYL- 4-PYRAZOLEBORONIC ACID PINACOL ESTER;1-METHYL-4-(4,4,5,5-TERAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE;1-methyl-4-(4，4，5，5-tetramethyl-1，3，2-dioxaborolan-2-yl)-1H-;1-Methyl-4-pyrazoleboronic acid pinacol ester, 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Methyl-4-(4,4,5-trimethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, 97+%;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole
• CAS: 761446-44-0
• MF: C10H17BN2O2
• MW: 208.07
• EINECS: 616-293-9
• Product Categories: Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronate Esters;Organometallic Reagents;Heterocyclic Building Blocks;Organoborons;Pyrazole;Boronic acid
• Mol File: 761446-44-0.mol

1-Methyl-4-pyrazole boronic acid pinacol ester Chemical Properties

• 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
• InChIKey: UCNGGGYMLHAMJG-UHFFFAOYSA-N
• SMILES: N1(C)C=C(B2OC(C)(C)C(C)(C)O2)C=N1
• CAS DataBase Reference: 761446-44-0(CAS DataBase Reference)

Safety Information

• Hazard Codes: Xn,F,Xi
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazard Note: Irritant/Flammable
• TSCA: No
• HazardClass: IRRITANT
• HS Code: 29349990
• Storage Class: 11 - Combustible Solids

1-Methyl-4-pyrazole boronic acid pinacol ester Usage And Synthesis

Chemical Properties

White to light yellow crystal powde

Uses

suzuki reaction

Uses

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.

References

[1] Patent: WO2018/93569, 2018, A1. Location in patent: Page/Page column 189
[2] Patent: WO2009/155527, 2009, A2. Location in patent: Page/Page column 137-138
[3] Patent: WO2005/85227, 2005, A1. Location in patent: Page/Page column 90-91

1-Methyl-4-pyrazole boronic acid pinacol ester Preparation Products And Raw materials

• Raw materials: Tetrahydrofuran-->Potassium hydroxide-->n-Butyllithium-->Iodomethane-->Trimethyl borate-->Methyl bromide-->Pinacol-->5A molecular sieve-->4-Bromopyrazole-->4-Iodo-1-methyl-1H-pyrazole-->4-Bromo-1-methylpyrazole-->4-Chloro-1-methylpyrazole-->1-Methyl-1H-pyrazole-4-boronic acid-->2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-->4-Pyrazoleboronic acid pinacol ester
• Preparation Products: 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester-->7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline-->1-(2,2-difluoroethyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole