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Pyrazole-4-boronic acid pinacol ester
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Name

Pyrazole-4-boronic acid pinacol ester

 EINECS -0
CAS No. 269410-08-4 Density 1.091 g/cm3
PSA 47.14000 LogP 0.70890
Solubility insoluble in water Melting Point 142-146 °C(lit.)
Formula C9H15BN2O2 Boiling Point 335.373 °C at 760 mmHg
Molecular Weight 194.041 Flash Point 156.628 °C
Transport Information N/A Appearance Off-white to tan powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 269410-08-4 (Pyrazole-4-boronic acid pinacol ester) Hazard Symbols IrritantXi, FlammableF
Synonyms

1H-Pyrazole-4-boronicacid pinacol ester;4,4,5,5-Tetramethyl-2-(1H-pyrazol-2-yl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(pyrazol-4-yl)-1,3,2-dioxaborolane;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)pyrazole;Pyrazol-4-ylboronicacid pinacol ester;

Article Data 25

Pyrazole-4-boronic acid pinacol ester Synthetic route

1029716-44-6

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

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In water at 10 - 25℃; for 4.083h;94%
With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In tert-butyl methyl ether; 1,2-dichloro-ethane at 0 - 20℃; Large scale;77.3%
With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In tert-butyl methyl ether; 1,2-dichloro-ethane at 0 - 20℃; Large scale;77.3%
2075-45-8

4-bromo-1H-pyrazole

73183-34-3

bis(pinacol)diborane

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane for 12h; Inert atmosphere; Reflux;94%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃;25%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Miyaura Borylation Reaction; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Miyaura Borylation Reaction; Inert atmosphere;
288-13-1

NH-pyrazole

25015-63-8

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

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; Glovebox; regioselective reaction;88%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 4h; Schlenk technique; Inert atmosphere;67%
15878-00-9

4-chloro-1H-pyrazole

73183-34-3

bis(pinacol)diborane

269410-08-4

pyrazole-4-boronic acid pinacol ester

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 0.5h;88%
552846-17-0

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
at 180℃;80.2%
at 180℃; for 0.0833333h;72%
121669-70-3

4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester

557087-01-1

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

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
With iPrBu2MgLi In 2-methyltetrahydrofuran at -20 - -10℃; Large scale;79%
557087-01-1

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

1150271-23-0

4-bromopyrazole-1-carboxylic acid tert-butyl ester

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
With n-Bu3MgLi In tetrahydrofuran at -20 - -10℃; Large scale;76%
288-13-1

NH-pyrazole

73183-34-3

bis(pinacol)diborane

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 21h; Inert atmosphere; Glovebox;56%
61676-62-8

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

1-trimethylsilyl-4-iodopyrazole

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
Stage #1: 4-iodo-1-trimethylsilylpyrazole With isopropylmagnesium chloride In tetrahydrofuran at -6 - 0℃; Inert atmosphere;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; Inert atmosphere;		54.8%
Stage #1: 4-iodo-1-trimethylsilylpyrazole With isopropylmagnesium chloride In tetrahydrofuran at -6 - 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran at -6 - 0℃;		54.8%
Stage #1: 4-iodo-1-trimethylsilylpyrazole With isopropylmagnesium chloride In tetrahydrofuran at -6 - 0℃; for 0.166667h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; for 2.17h;		54.8%
3469-69-0

4-iodopyrazole

25015-63-8

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

269410-08-4

pyrazole-4-boronic acid pinacol ester

Conditions
ConditionsYield
Stage #1: With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 80℃; for 18h;
Stage #2: 4-iodopyrazole; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In 1,4-dioxane at 80℃; for 18h;

Pyrazole-4-boronic acid pinacol ester Specification

The IUPAC name of 1H-Pyrazole,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- is 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. With the CAS registry number 269410-08-4, it is also named as 1H-Pyrazole-4-boronic acid, pinacol ester. The product's categories are Pyrazole Series; API Intermediates; Boronic acid. It is off-white to tan powder which is insoluble in water. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)#H bond acceptors: 4; (2)#H bond donors: 1; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 47.14 Å2; (5)Index of Refraction: 1.487; (6)Molar Refractivity: 51.18 cm3; (7)Molar Volume: 177.841 cm3; (8)Polarizability: 20.29×10-24 cm3; (9)Surface Tension: 37.054 dyne/cm; (10)Flash Point: 156.628 °C; (11)Enthalpy of Vaporization: 55.549 kJ/mol; (12)Boiling Point: 335.373 °C at 760 mmHg; (13)Vapour Pressure: 0 mmHg at 25°C; (14)Rotatable Bond Count: 1; (15)Exact Mass: 194.122658; (16)MonoIsotopic Mass: 194.122658; (17)Topological Polar Surface Area: 47.1; (18)Heavy Atom Count: 14; (19)Complexity: 217.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:B1(OC(C(O1)(C)C)(C)C)c2c[nH]nc2
2. InChI:InChI=1/C9H15BN2O2/c1-8(2)9(3,4)14-10(13-8)7-5-11-12-6-7/h5-6H,1-4H3,(H,11,12)

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