1H-Indazole-5-boronic acid

Base Information

• Chemical Name: 1H-Indazole-5-boronic acid
• CAS No.: 338454-14-1
• Molecular Formula: C7H7BN2O2
• Molecular Weight: 161.956
• Hs Code.: 29339980
• European Community (EC) Number: 683-693-8
• ChEMBL ID: CHEMBL3236907
• DSSTox Substance ID: DTXSID40590551
• Wikidata: Q72482756
• Mol file: 338454-14-1.mol

Synonyms:1H-Indazole-5-boronic acid;338454-14-1;(1H-indazol-5-yl)boronic acid;1H-indazol-5-ylboronic acid;Indazole-5-boronic acid;C7H7BN2O2;MFCD06739151;B-1H-INDAZOL-5-YL-BORONIC ACID;Boronic acid, B-1H-indazol-5-yl-;1H-Indazol-5-yl-5-boronic acid;1H-INDAZOLE-5-BORONICACID;5-indazolylboronic acid;SCHEMBL23786;1361253-30-6;(2H-Indazol-5-yl)boronic acid;CHEMBL3236907;DTXSID40590551;CLVPGJWAMIADSY-UHFFFAOYSA-N;CS-D0077;AKOS005255244;1H-Indazole-5-boronic acid, >=95%;AM81174;PB30851;PS-9449;NCGC00249487-01;SY020865;A25134;EN300-212656;J-500185

Chemical Property of 1H-Indazole-5-boronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 175-180°C
• Refractive Index: 1.671
• Boiling Point: 457.012 °C at 760 mmHg
• Flash Point: 230.193 °C
• PSA: 69.14000
• Density: 1.423 g/cm³
• LogP: -0.75730
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 162.0600576
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

1H-Indazole-5-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)NN=C2)(O)O
• Uses: Reactant for:Preparation of thieno[3,2-d]pyrimidines as Tpl2 kinase inhibitorsSynthesis of pyridinyl benzonaphthyridinones as mTOR inhibitors for the treatment of cancerNovel bisphosphonate inhibitors of human farnesyl pyrophosphate synthasePreparation of diazabicycloheptanes as α7 neurinal nicotinic receptor affectorsPreparation of pyrazolopyrimidinamine derivatives with tyrosine and phosphinositide kinase inhibitory activity

Technology Process of 1H-Indazole-5-boronic acid

There total 2 articles about 1H-Indazole-5-boronic acid 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: 72.0%

boric acid tributyl ester (688-74-4) + 5-bromo-1-(triisopropylsilyl)-1H-indazole (1033818-69-7) → 1H-indazol-5-ylboronic acid (338454-14-1)

Guidance literature:

With n-butyllithium; at -78 - 20 ℃; for 0.5h; Inert atmosphere;

Reference yield: 19.0%

5-bromo-1H-indazole (53857-57-1) → 1H-indazol-5-ylboronic acid (338454-14-1)

Guidance literature:

5-bromo-1H-indazole; With n-butyllithium; In diethyl ether; hexane; at -20 - 30 ℃; for 3h;

With Trimethyl borate; In diethyl ether; hexane; at -70 - 20 ℃; for 15h;

With hydrogenchloride; water;

Reference yield: 77.0%

1H-indazol-5-ylboronic acid (338454-14-1) + 2-(4-fluorophenyl)-3-iodo-N,N-dimethylimidazo[1,2-a]pyrazin-8-amine → 2-(4-fluorophenyl)-3-(1H-indazol-5-yl)-N,N-dimethylimidazo[1,2-a]pyrazin-8-amine

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 100 ℃; Sealed tube;

DOI:10.1016/j.ejmech.2020.112956

upstream raw materials:

5-bromo-1H-indazole

boric acid tributyl ester

5-bromo-1-(triisopropylsilyl)-1H-indazole

Downstream raw materials:

1-(cyclohexylmethyl)-6-(1H-indazol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

C₁₇H₁₉N₅O

C₁₈H₂₁N₅O

N-(3,4-dichlorobenzyl)-4-(1H-indazol-5-yl)pyrimidin-2-amine

Refernces

• 1、 -. "Substituted 5-benzyl-2,4-diaminopyrimidines". Page column 24. . Retrieved 2010/02/09.