1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
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1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
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CAS No:
761446-44-0
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Formula:
C10H17BN2O2
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Chemical Name:
1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
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Synonyms:
1H-Pyrazole,1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;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-Methylpyrazole-4-boronic 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-methyl-1H-pyrazole;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-methylpyrazole;1-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;(1-Methyl-1H-pyrazol-4-yl)boronic acid pinacol ester;1-Methyl-1H-pyrazole-4-boronic acid pinacol ester;1-Methyl-4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
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CAS No:
1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Basic Attributes
208.07
208.07
1312995-182-4
DTXSID40378816
2933199090
Characteristics
36.3
0.71930
Off-white to yellow Crystals
1.1±0.1 g/cm3
67-69 °C
308.3°C at 760 mmHg
140.3±20.4 °C
1.505
Slightly soluble in water.
Refrigerator (+4°C)
Safety Information
IRRITANT
3
22-36/37/38
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
H302
|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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 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
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-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
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