6-INDAZOLYBORONIC ACID

Base Information

• Chemical Name: 6-INDAZOLYBORONIC ACID
• CAS No.: 885068-10-0
• Molecular Formula: C7H7BN2O2
• Molecular Weight: 161.956
• Hs Code.: 29339980
• Mol file: 885068-10-0.mol

Synonyms:Boronicacid, 1H-indazol-6-yl- (9CI);1H-Indazol-6-ylboronic acid;

Chemical Property of 6-INDAZOLYBORONIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 112-117°C
• Refractive Index: 1.671
• Boiling Point: 457.012 °C at 760 mmHg
• PKA: 8.15±0.30(Predicted)
• Flash Point: 230.193 °C
• PSA: 69.14000
• Density: 1.423 g/cm³
• LogP: -0.75730
• Storage Temp.: 2-8°C

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

Indazole-6-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant for preparation of:Bicyclic hydroxyphenylmethanone derivatives as hydroxysteroid dehydrogenase inhibitorsBisphosphonate inhibitors of human farnesyl pyrophosphate synthaseIndazolyl benzoimidazoles as PKC-ζ inhibitorsPyrazolopyrimidinamine derivatives and their tyrosine and phosphinositide kinase inhibitory activity

Technology Process of 6-INDAZOLYBORONIC ACID

There total 1 articles about 6-INDAZOLYBORONIC 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: 52.0%

6-bromo-1H-indazole (79762-54-2) + boric acid tributyl ester (688-74-4) → (1H-indazol-6-yl)boronic acid (885068-10-0)

Guidance literature:

6-bromo-1H-indazole; With n-butyllithium; In tetrahydrofuran; pentane; at -78 ℃; for 3h; Inert atmosphere;

boric acid tributyl ester; In tetrahydrofuran; pentane; at 20 ℃; Inert atmosphere;

Reference yield: 96.0%

(1H-indazol-6-yl)boronic acid (885068-10-0) → 1H-indazol-6-ol (23244-88-4)

Guidance literature:

With water; caesium carbonate; hydrazine hydrate; at 80 ℃; for 12h;

DOI:10.1039/c4ra05589f

Reference yield: 66.0%

(1H-indazol-6-yl)boronic acid (885068-10-0) + tert-butyl (S)-4-(3-((1-(3-bromo-4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)oxy)benzoyl)piperidin-4-yl)oxy)-5-fluorophenyl)piperazine-1-carboxylate → tert-butyl (S)-4-(3-((1-(4-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)oxy)-3-(1H-indazol-6-yl)benzoyl)piperidin-4-yl)oxy)-5-fluorophenyl)piperazine-1-carboxylate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 90 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00596

upstream raw materials:

6-bromo-1H-indazole

boric acid tributyl ester

Downstream raw materials:

1H-indazol-6-ol

Refernces

• 1、 Yao, Xia,Sun, Xiuyun,Jin, Shuyu,Yang, Ling,Xu, Hongjiang,Rao, Yu. "Discovery of 4-Aminoquinoline-3-carboxamide derivatives as potent reversible Bruton's tyrosine kinase inhibitors for the treatment of rheumatoid arthritis". . p. 6561 - 6574. Retrieved 2019/08/20.