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761446-44-0

Basic Information
CAS No.: 761446-44-0
Name: 1-Methyl-4-pyrazole boronic acid pinacol ester
Article Data: 22
Molecular Structure:
Molecular Structure of 761446-44-0 (1-Methyl-4-pyrazole boronic acid pinacol ester)
Formula: C10H17BN2O2
Molecular Weight: 208.068
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)pyrazole;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;
EINECS: 616-293-9
Density: 1.05 g/cm3
Melting Point: 59-64 °C(lit.)
Boiling Point: 308.3 °C at 760 mmHg
Flash Point: 140.3 °C
Solubility: Slightly soluble in water.
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn, FlammableF, IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36-37/39
PSA: 36.28000
LogP: 0.71930
Synthetic route
269410-08-4

pyrazole-4-boronic acid pinacol ester

74-88-4

methyl iodide

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 4h;93%
With sodium hydride In tetrahydrofuran at 20℃;90%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 3h;72%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 60℃; for 8h; Inert atmosphere;63%
76-09-5

2,3-dimethyl-2,3-butane diol

847818-55-7

(1-methyl-1H-pyrazol-4-yl)boronic acid

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With 4 A molecular sieve In tetrahydrofuran at 20℃; for 2h;80%
With alkaline lipase In tetrahydrofuran; ethanol at -15 - -10℃; for 12h; Concentration; Reagent/catalyst; Molecular sieve; Large scale; Enzymatic reaction;92.5 kg
930-36-9

1-methyl-1H-pyrazole

76-09-5

2,3-dimethyl-2,3-butane diol

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium
Stage #2: With Trimethyl borate In tetrahydrofuran at -90℃;
Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran
80%
15803-02-8

4-bromo-1-methyl-1H-pyrazole

73183-34-3

bis(pinacol)diborane

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 5h; Inert atmosphere;27.1%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Suzuki-Miyaura Coupling;
269410-08-4

pyrazole-4-boronic acid pinacol ester

74-83-9

methyl bromide

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With caesium carbonate In acetonitrile Inert atmosphere;
76-09-5

2,3-dimethyl-2,3-butane diol

C19H43BN2O4

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Reflux;
35852-81-4

4-chloro-1-methyl-1H-pyrazole

73183-34-3

bis(pinacol)diborane

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos In ethanol at 20℃; for 2h;
39806-90-1

4-iodo-1-methyl-1H-pyrazole

61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 4-iodo-1-methyl-1H-pyrazole With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; for 1.5h;
1 g
930-36-9

1-methyl-1H-pyrazole

25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

847818-74-0

1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

B

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In hexane at 20℃; Glovebox; Inert atmosphere;
Stage #2: With 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; Glovebox; Inert atmosphere;
Stage #3: 1-methyl-1H-pyrazole In hexane at 20℃; for 5h; Reagent/catalyst; Solvent; Glovebox; Inert atmosphere; Overall yield = 67 percent; regioselective reaction;
269410-08-4

pyrazole-4-boronic acid pinacol ester

methyl halide

methyl halide

761446-44-0

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With potassium carbonate In acetonitrile
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Chemistry

Molecule structure of 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0):

IUPAC Name: 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole 
Molecular Weight: 208.06518 g/mol
Molecular Formula: C10H17BN2O2 
Density: 1.05 g/cm3 
Melting Point: 59-64 °C(lit.)
Boiling Point: 308.3 °C at 760 mmHg 
Flash Point: 140.3 °C
Index of Refraction: 1.505
Molar Refractivity: 58.29 cm3
Molar Volume: 196.4 cm3
Surface Tension: 32.1 dyne/cm
Enthalpy of Vaporization: 52.71 kJ/mol
Vapour Pressure: 0.00125 mmHg at 25 °C 
Storage Temp.: refrigerator (+4 °C) 
H-Bond Acceptor: 3
Rotatable Bond Count: 1
Exact Mass: 208.138308
MonoIsotopic Mass: 208.138308
Topological Polar Surface Area: 36.3
Heavy Atom Count: 15
Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)C
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
Product Categories of 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0): Organoborons;Pyrazole;Boronic acid;Heterocyclic Building Blocks

Safety Profile

Hazard Codes: HarmfulXn, FlammableF, IrritantXi
Risk Statements: 22-36/37/38 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant/Flammable
HazardClass: IRRITANT

Specification

 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0) is also named as 1H-pyrazole, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- ; 1-Methyl-1H-pyrazole-4-boronic acid, pinacol ester ; 1-Methyl-4-pyrazoleboronic acid pinacol ester ; 1-Methylpyrazole-4-Boronic Acid Pinacol Ester . 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS NO.761446-44-0) is white to light yellow crystal powder.