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

Base Information

• Chemical Name: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate
• CAS No.: 552846-17-0
• Molecular Formula: C14H23BN2O4
• Molecular Weight: 294.159
• Hs Code.: 29339900
• European Community (EC) Number: 676-377-6
• DSSTox Substance ID: DTXSID80584474
• Wikidata: Q72450575
• Mol file: 552846-17-0.mol

Synonyms:552846-17-0;1-Boc-pyrazole-4-boronic acid pinacol ester;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate;1-Boc-4-pyrazoleboronic acid pinacol ester;n-boc-pyrazole-4-boronic acid pinacol ester;1-Boc-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate;MFCD05663873;tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate;1-tert-butoxycarbonyl-1h-pyrazole-4-boronic acid pinacol ester;tert-Butyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate;(1-(TERT-BUTOXYCARBONYL)-1H-PYRAZOL-4-YL)BORONIC ACID PINACOL ESTER;[1-(TERT-BUTOXYCARBONYL)-1H-PYRAZOL-4-YL]BORONIC ACID PINACOL ESTER;1-(tert-Butoxycarbonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;1-tert-Butoxycarbonyl-4-1H-pyrazoleboronic acid;2-(1-Boc;SCHEMBL141413;DTXSID80584474;IPISOFJLWYBCAV-UHFFFAOYSA-N;1-tert-butoxycarbonyl-1h-pyrazole-4-boronic acid, pinacol ester;BCP22825;AKOS005258263;AB21992;AM85816;AS-2962;BCP9000048;CS-W003233;HY-W003233;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole-1-carboxylic acid tert-butyl ester;SY006077;1-Boc-pyrazol-4-boronic acid pinacol ester;n-boc-4-pyrazole boronic acid pinacol ester;1-boc-4-pyrazole boronic acid pinacol ester;1-Boc-Pyrazole-4-Boronicacid Pinacoal Ester;B5203;1-Boc-pyrazolyl-4-boronic Acid Pinacol Ester;EN300-92083;N-Boc-pyrazole-4-boronic acid pinaxcol ester;A830571;1-Boc-pyrazole-4-boronic acid pinacol ester, 97%;J-524619;PipClU?Chloro-dipiperidinocarbenium hexafluorophosphate;Z1263597321;1-(tert-Butoxycarbonyl)pyrazolyl-4-boronic Acid Pinacol Ester;1-Tert-butoxycarbonyl-4-1H-pyrazoleboronic acid pinacol ester;N1-BOC-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-(t-butoxycarbonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole;2-(1-tert-Butoxycarbonyl-4-pyrazolyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;t-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate;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-pyrazol-1-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxy late;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-1-carboxylate;tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-carboxylate;tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate;TERT-BUTYL4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRAZOLE-1-CARBOXYLATE;1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate;1H-PYRAZOLE-1-CARBOXYLIC ACID, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL ESTER;2-Methyl-2-propanyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)-1h-pyrazole-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE-1-CARBOXYLICACID TERT-BUTYL ESTER;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylic acid-tert-butyl ester;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)-pyrazole-1-carboxylic acid tert-butyl ester

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

Chemical Property:

• Appearance/Colour: white to beige crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 82-86 °C(lit.)
• Refractive Index: 1.502
• Boiling Point: 387.895 °C at 760 mmHg
• PKA: -1.20±0.12(Predicted)
• Flash Point: 188.393 °C
• PSA: 62.58000
• Density: 1.097 g/cm³
• LogP: 1.96550
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: soluble in Methanol
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 294.1750874
• Heavy Atom Count: 21
• Complexity: 404

Purity/Quality:

98% ^*data from raw suppliers

1-Boc-pyrazole-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)C(=O)OC(C)(C)C
• 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.

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

There total 8 articles about tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.68%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate (552846-17-0)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield: 85.7%

4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester (121669-70-3) + bis(pinacol)diborane (73183-34-3) → tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate (552846-17-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate; In isopropyl alcohol; for 16h; Inert atmosphere; Reflux;

Reference yield: 83.0%

bis(pinacol)diborane (73183-34-3) + tert-butyl 1H-pyrazole-1-carboxylate (219580-32-2) → tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate (552846-17-0)

Guidance literature:

bis(pinacol)diborane; With C₂₄H₂₈ClIrN₂O; In tetrahydrofuran; at 65 ℃; for 1h; Sealed tube; Inert atmosphere;

tert-butyl 1H-pyrazole-1-carboxylate; In tetrahydrofuran; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04210

upstream raw materials:

pyrazole-4-boronic acid pinacol ester

di-tert-butyl dicarbonate

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

tert-butyl 1H-pyrazole-1-carboxylate

Downstream raw materials:

4-(1H-pyrazol-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

tert-butyl 4-(4-(2-fluoro-4-(2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamido)phenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrazole-1-carboxylate

Tert-butyl 4-(4-(2-(2-(4-benzhydrylpiperazin-1-yl)-2-oxoethoxy)acetamido)-3-(methoxycarbonyl)phenyl)-1H-pyrazole-1-carboxylate

N₂-(4-{[2-(diethylamino)ethyl]oxy}phenyl)-N₄-[2-(methyloxy)phenyl]-5-(1H-pyrazol-4-yl)-2,4-pyrimidinediamine

Refernces

• 1、 -. "Synthesis method of pyrazole-4-pinacolato diboron". Paragraph 0020-0023. . Retrieved 2020/02/14.
• 2、 -. "RHO-ASSOCIATED PROTEIN KINASE INHIBITOR, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, AS WELL AS PREPARATION METHOD AND USE THEREOF". Paragraph 0111; 0112; 0233; 0234. . Retrieved 2019/01/11.