1-Methyl-4-pyrazole boronic acid pinacol ester
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1-Methyl-4-pyrazole boronic acid pinacol ester
structure -
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CAS No:
761446-44-0
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Formula:
C10H17BN2O2
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Chemical Name:
1-Methyl-4-pyrazole boronic acid pinacol ester
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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+%;2-(1-Methylpyrazol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- Categories:
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CAS No:
1-Methyl-4-pyrazole boronic acid pinacol ester Basic Attributes
208.07
208.07
616-293-9
No
DTXSID40378816
Off-white to yellow
29349990
Characteristics
36.3
0.71930
Off-white to yellow Crystals
1.05±0.1 g/cm3(Predicted)
59-64 °C(lit.)
308.3±15.0 °C(Predicted)
140.3±20.4 °C
1.505
Slightly soluble in water.
Refrigerator (+4°C)
2.09±0.10(Predicted)
Keep in dark place,Sealed in dry,Room Temperature
Safety Information
IRRITANT
3
Xn,F,Xi
26-36-37/39
Xn,F,Xi
Irritant/Flammable
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
22-36/37/38
|Warning|H302 (98.18%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 55 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
1-Methyl-4-pyrazole boronic acid pinacol ester Use and Manufacturing
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 NHTo the solution of 4-pinacolatoboron-lH-pyrazole (1.0 g, 5.0 mmol) in THF (30 mL) was added NaH (0.4 g, 10 mmol). After addition of NaH was completed, to the reaction mixture was added CHTo a solution of 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1H- pyrazole (0. 19g, 1.0 mmol) in 4 ml DMF was added Mel (0. 067 ml, 1.1 eq) and Cs2C03 (0.39g, 1.2 eq). The reaction mixture was stirred at RT for 3h. The solution was taken up into EtOAc, washed with water, brine, dried over Na2SO4 and concentrated. 150mg crude product was obtained (yield 72percent).A suspension of 4-bromo-l -methyl- lH-pyrazole (2 g, 12.42 mmol), 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl- 2, 2'-bi(l, 3, 2-dioxaborolane) (3.47 g, 13.66 mmol), KOAc (2.438 g, 24.84 mmol), PdClTo 1-methyl-4-iodopyrazole (1.0 g) and 10 mL of THF, Under the protection of nitrogen, slowly add isopropylmagnesium chloride/lithium chloride solution (3.97mL), the temperature during the dropwise addition does not exceed 0 °C, After the addition, stir for 1 h, then at 0 ° C, Slowly add isopropyl pinacol borate (1.11g) to control the temperature not to exceed 0 ° C, and then stir at room temperature for 1.5 h after the addition.After the reaction was completed, 10 mL of a saturated ammonium chloride solution was added dropwise.Quenched.Then add 50 mL of ethyl acetate and 10 mL of saturated ammonium chloride solution.The organic layer was separated, and the aqueous layer was extracted twice with 50 mL of ethyl acetate. The organic layer was combined and dried over anhydrous Na2SO'Dry under reduced pressure, The title product (1 g) was obtained.
suzuki reaction
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.
Computed Properties
Molecular Weight:208.07
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:208.1383080
Monoisotopic Mass:208.1383080
Topological Polar Surface Area:36.3
Heavy Atom Count:15
Complexity:242
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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1-Methyl-4-pyrazole boronic acid pinacol ester
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