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4-Pyrazoleboronic acid pinacol ester

Product Name
4-Pyrazoleboronic acid pinacol ester
CAS No.
269410-08-4
Chemical Name
4-Pyrazoleboronic acid pinacol ester
Synonyms
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE;PYRAZOLE-4-BORONIC ACID PINACOL ESTER;4-Pyrazoleboronic acid pinaol ester;4,4,5,5-TETRAMETHYL-2-(1H-PYRAZOL-4-YL)-1,3,2-DIOXABOROLANE;Baricitinib-005;Triazolam Impurity 6;eboronic acid pinacoL;Crizotinib Intermediates 4;Pinacol Pyrazol-4-ylboronate;4-Pyrazoleboronic acid pinacol
CBNumber
CB6449821
Molecular Formula
C9H15BN2O2
Formula Weight
194.04
MOL File
269410-08-4.mol
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4-Pyrazoleboronic acid pinacol ester Property

Melting point:
142-146 °C (lit.)
Boiling point:
335.4±15.0 °C(Predicted)
Density 
1.09±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
DMSO, Ethyl Acetate, Methanol
pka
13.36±0.50(Predicted)
form 
Powder
color 
Off-white to tan
Water Solubility 
insoluble
InChI
InChI=1S/C9H15BN2O2/c1-8(2)9(3,4)14-10(13-8)7-5-11-12-6-7/h5-6H,1-4H3,(H,11,12)
InChIKey
TVOJIBGZFYMWDT-UHFFFAOYSA-N
SMILES
N1C=C(B2OC(C)(C)C(C)(C)O2)C=N1
CAS DataBase Reference
269410-08-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi,F
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
Hazard Note 
Irritant/Flammable
TSCA 
No
HS Code 
29331990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
525057
Product name
4-Pyrazoleboronic acid pinacol ester
Purity
97%
Packaging
1g
Price
$43.44
Updated
2025/07/31
Sigma-Aldrich
Product number
525057
Product name
4-Pyrazoleboronic acid pinacol ester
Purity
97%
Packaging
5g
Price
$55.23
Updated
2025/07/31
TCI Chemical
Product number
T2756
Product name
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole
Purity
>97.0%(GC)
Packaging
1g
Price
$38
Updated
2025/07/31
TCI Chemical
Product number
T2756
Product name
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole
Purity
>97.0%(GC)
Packaging
5g
Price
$126
Updated
2025/07/31
Strem Chemicals
Product number
05-1048
Product name
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, min. 97%
Packaging
1g
Price
$94
Updated
2024/03/01
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4-Pyrazoleboronic acid pinacol ester Chemical Properties,Usage,Production

Chemical Properties

Off-white to tan powder

Uses

4-Pyrazoleboronic Acid Pinacol Ester is used in the preparation of Rho kinase (ROCK) inhibitors as wella s other biologically active compounds.

Uses

1H-Pyrazole-4-boronic acid pinacol ester is a useful reagent for Suzuki-Miyaura cross-couplings as well as Ruthenium-catalyzed asymmetric hydrogenation. It is also used as reagent for preparing VEGF, Aurora, RHO (ROCK), Janus Kinase 2, c-MET, ALK, S-nitrsoflutathione reductase, CDC7, Acetyl-CoA carboxylase inhibitors as well as other biologically active compounds.

Uses

Reagent used for

  • Suzuki-Miyaura cross-couplings
  • Ruthenium-catalyzed asymmetric hydrogenation

Reagent used in preparation of inhibitors of many highly significant therapeutic enzymes and kinases containing the privileged scaffold pyrazole, including
  • VEGF
  • Aurora
  • Rho (ROCK)
  • Janus Kinase 2 (JAK)
  • c-MET
  • ALK
  • S-nitrosoglutathione reductase
  • CDC7
  • Acetyl-CoA carboxylase
  • Prosurvival Bcl-2 protein
  • Viral RNA-Dependent RNA polymerase
  • Long Chain Fatty Acid Elongase 6
  • PI3
  • AKT
  • Chk1
  • Protein Kinase B

Synthesis

1029716-44-6

269410-08-4

General procedure for the synthesis of 4-pyrazole boronic acid pinacol ester from 1-(1-ethoxyethyl)-4-pyrazoleboronic acid pinacol ester: 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (60.00 g, 224 mmol) was mixed with cyclopentyl methyl ether (CPME. 120 mL) and 2,3-dimethyl-2,3-butanediol (26.49 g, 224 mmol) were mixed. The reaction mixture was cooled to 5-10 °C, then a solution of anhydrous hydroquinone (HQ) in CPME (3.1 M, 86.8 mL, 269 mmol) was slowly added over 15 min, followed by additional CPME (15 mL). The reaction mixture was stirred at 20-25 °C and the progress of the reaction was monitored by TLC.After 7 h, additional hydrochloric acid solution (3 mL, 9.3 mmol) was added to the reaction mixture and stirring was continued for 15 h to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole hydrochloride, which did not require isolation. The temperature of the reaction mixture was raised to 20°C after addition of additional hydrochloric acid solution within 10 min. Additional CPME (10 mL) was added and the reaction mixture was stirred for 15 min and then cooled in an ice bath.After 3 h, the reaction mixture was filtered and the solid (triethylamine hydrochloride) was washed with cold CPME (3 x 60 mL). The filtrate and washings were combined to give 426 g of a solution containing 102.3 mg of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole. The solution (8.15 g in total, 94% yield) was used directly in the next step.

References

[1] Patent: WO2016/205487, 2016, A1. Location in patent: Page/Page column 27-28
[2] Patent: US2014/256941, 2014, A1. Location in patent: Paragraph 0166

4-Pyrazoleboronic acid pinacol ester Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 4-Pyrazoleboronic acid pinacol ester manufacturers

Shaanxi Xianhe Biotech Co., Ltd
Product
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 269410-08-4
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
1000kg
Release date
2025-04-17
Hubei Lidu New Material Technology Co., Ltd
Product
4-Pyrazoleboronic acid pinacol 269410-08-4
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
20TON
Release date
2024-12-11
Hubei Lidu New Material Technology Co., Ltd
Product
4-Pyrazoleboronic acid pinacol ester 269410-08-4
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
20TON
Release date
2024-12-11

269410-08-4, 4-Pyrazoleboronic acid pinacol esterRelated Search:

Tris(trimethylsilyl)phosphate Pyraclostrobin Pinacol 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Pyrazole Zolpidem tartrate PROPARGYL BENZOATE 98 Propyl 4-bromo-3-methylbenzoate Propyl 3-bromo-2-chloroisonicotinate 4,4,5,5-Tetramethyl-2-(prop-1-enyl)-1,3,2-dioxaborolane Pyrazolo[1,5-a]pyridine-3-carbonitrile PYRROLO[2,1-F][1,2,4]TRIAZINE-2,4-DIAMINE Pyrido[3,4-b]pyrazine (6CI,7CI,8CI,9CI) 4-Pyridineboronic acid pinacol ester Pyridine, 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)- 5-Methyl-1-phenyl-1H-pyrazole-4-boronic acid pinacol ester 97%,5-METHYL-1-PHENYL-1H-PYRAZOLE-4-BORONIC ACID PINACOL ESTER Zolpidem 1-Methyl-4-pyrazole boronic acid pinacol ester

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  • 3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 1H-pyrazol-4-ylboronate
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  • 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORLAN-2-YL)-1H-PYRAZOLE
  • Crizotinib Intermediates 4
  • Triazolam Impurity 6
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  • 4-Pyrazoleboronic acid pinacol
  • 4,4,5,5-Tetramethyl-2-(1H-Pyrazol-4-Yl)-1,3,2-Diox
  • 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole - [T8901]
  • 4-Pyrazoleboronic acid pinacol este
  • 269410-08-4
  • CH34C2O2BC3N2H3
  • C9H15BN2O2
  • Heteroaryl
  • Organometallic Reagents
  • Boronic Acids and Derivatives
  • Boronate Esters
  • organic or inorganic borate
  • Pyrazole series
  • API intermediates
  • Boronic acid
  • OLED materials,pharm chemical,electronic
  • 269410-08-4