4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-QUINOLINE

Base Information

• Chemical Name: 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-QUINOLINE
• CAS No.: 1035458-54-8
• Molecular Formula: C15H18BNO2
• Molecular Weight: 255.124
• Hs Code.: 2934999090
• Mol file: 1035458-54-8.mol

Synonyms:1H-Imidazo[4,5-c]quinoline, 4-chloro-1-(2-methylpropyl)-

Chemical Property of 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-QUINOLINE

Chemical Property:

• Appearance/Colour: Almost crystalline powder
• Boiling Point: 386.5±15.0 °C(Predicted)
• PKA: 4.16±0.46(Predicted)
• PSA: 31.35000
• Density: 1.10
• LogP: 2.53400
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Quinoline-4-boronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Use Description: 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline, a complex chemical compound, has diverse applications across various fields. In the field of organic chemistry, it is often employed as a ligand in coordination chemistry and catalysis, facilitating various chemical reactions and enabling the synthesis of complex organic molecules. In the pharmaceutical industry, this compound may serve as a key intermediate in the development of novel drug compounds due to its unique structural properties. Additionally, in materials science and the production of advanced materials, it can be used as a building block for creating specialized materials, potentially finding application in the development of organic electronics and optoelectronic devices. Its versatility as a catalyst, intermediate, and materials precursor highlights its significance in advancing chemical research, drug discovery, and materials innovation in different fields.

Technology Process of 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-QUINOLINE

There total 3 articles about 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-QUINOLINE 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: 32.0%

4-chloroquinoline (611-35-8) + bis(pinacol)diborane (73183-34-3) → quinoline (91-22-5) + 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinoline (1035458-54-8)

Guidance literature:

With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel⁽⁰⁾; potassium methanolate; In hexane; at 25 ℃; for 6h; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.0c08834

Reference yield: 30.0%

→ 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinoline (1035458-54-8)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 4h; Inert atmosphere;

Reference yield:

bis(pinacol)diborane (73183-34-3) + 4-bromoquinoline (3964-04-3,850917-90-7) → 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinoline (1035458-54-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 20 - 100 ℃; for 2h; Inert atmosphere;

upstream raw materials:

bis(pinacol)diborane

4-bromoquinoline

4-chloroquinoline

Downstream raw materials:

4-phenylquinoline

phenyl-quinolin-4-yl-amine

Refernces

• 1、 Wang, Xin,Liu, Wei-Gang,Tung, Chen-Ho,Wu, Li-Zhu,Cong, Huan. "A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions". supporting information. p. 8158 - 8163. Retrieved 2019/09/07.
• 2、 -. "2-PYRIDYL SUBSTITUTED IMIDAZOLES AS ALK5 AND/OR ALK4 INHIBITORS". Page/Page column 27; 28. . Retrieved 2013/03/26.