1-Boc-pyrazole-4-boronic acid pinacol ester CAS 552846-17-0

Introduction：Basic information about 1-Boc-pyrazole-4-boronic acid pinacol ester CAS 552846-17-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

1-Boc-pyrazole-4-boronic acid pinacol ester Basic information

• Product Name: 1-Boc-pyrazole-4-boronic acid pinacol ester
• Synonyms: 1-Boc-4-pyrazoleboronic acid pinacol ester, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-Boc-pyrazole, tert-Butyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pyrazolecarboxylate;TERT-BUTYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE CARBOX., 97%;1-tert-Butoxycarbonyl-4-1H-pyrazoleboronic acid;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylic acid tert-butyl e;1-BOC-PYRAZOLE-4-BORONIC ACID PINACOL ESTER, 97%;1-TERT-BUTOXYCARBONYL-4-1H-PYRAZOLBORONIC ACID PINACOL ESTER;N-Boc-pyrazole-4-boronic acid pinaxcol ester;1-BOC- 4-PYRAZOLEBORONIC ACID PINACOL ESTER
• CAS: 552846-17-0
• MF: C14H23BN2O4
• MW: 294.15
• Product Categories: Boric Acid| Boric Acid Ester|Potassium Trifluoroborate
• Mol File: 552846-17-0.mol

1-Boc-pyrazole-4-boronic acid pinacol ester Chemical Properties

• Melting point: 82-86 °C (lit.)
• Boiling point: 387.9±34.0 °C(Predicted)
• density: 1.09±0.1 g/cm3(Predicted)
• storage temp.: 2-8°C
• solubility: soluble in Methanol
• form: Crystalline Powder
• pka: -1.20±0.12(Predicted)
• color: White to beige
• Water Solubility: insoluble
• InChI: InChI=1S/C14H23BN2O4/c1-12(2,3)19-11(18)17-9-10(8-16-17)15-20-13(4,5)14(6,7)21-15/h8-9H,1-7H3
• InChIKey: IPISOFJLWYBCAV-UHFFFAOYSA-N
• SMILES: N1(C(OC(C)(C)C)=O)C=C(B2OC(C)(C)C(C)(C)O2)C=N1

Safety Information

• Hazard Codes: Xn
• Risk Statements: 36/37/38-22
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• HS Code: 29339900
• Storage Class: 11 - Combustible Solids

1-Boc-pyrazole-4-boronic acid pinacol ester Usage And Synthesis

Chemical Properties

white to beige crystalline powder

Uses

1-Boc-pyrazole-4-boronic Acid Pinacol Ester is used as a reagent in the synthesis of several inhibitors including thieno[3,2-c]pyridin-4-amines which are a novel series of Bruton’s tyrosine kinase (BTK) inhibitors which can be used in drug design.

Synthesis

269410-08-4

24424-99-5

552846-17-0

4-Pyrazoleboronic acid pinacol ester (1.16 g, 6.0 mmol) and di-tert-butyl dicarbonate (1.58 g, 7.2 mmol) were used as raw materials and dissolved in dichloromethane (40 mL). A catalytic amount of 4-dimethylaminopyridine (102 mg, 0.84 mmol) was added and the reaction was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction system and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride solution and then the solvent was removed by rotary evaporation to give the crude product 1-Boc-pyrazole-4-boronic acid pinacol ester (1.5 g, 85% yield).

References

[1] Patent: CN103936728, 2016, B. Location in patent: Paragraph 0177; 0203; 0204; 0205
[2] Patent: US2006/46991, 2006, A1. Location in patent: Page/Page column 68
[3] Patent: WO2018/154466, 2018, A1. Location in patent: Paragraph 001162; 001164; 001165
[4] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 58
[5] Patent: WO2004/56727, 2004, A2. Location in patent: Page 97

1-Boc-pyrazole-4-boronic acid pinacol ester Preparation Products And Raw materials

• Raw materials: tert-Butyl 4-iodopyrazole-1-carboxylate-->1-Boc-4-bromopyrazole-->tert-Butyl 1H-pyrazole-1-carboxylate-->Di-tert-butyl dicarbonate-->4-Pyrazoleboronic acid pinacol ester-->Dichloromethane-->Pinacolborane-->4-Dimethylaminopyridine-->Bis(pinacolato)diboron
• Preparation Products: LMI070-->1H-Pyrazole-1-carboxylic acid, 4-(3-bromophenyl)-, 1,1-dimethylethyl ester-->1H-Pyrrolo[2,3-b]pyridine, 1-(phenylsulfonyl)-5-(1H-pyrazol-4-yl)--->Pyrido[2,3-d]pyrimidin-7(8H)-one, 2-amino-8-cyclopentyl-4-methyl-6-(1H-pyrazol-4-yl)-