2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 922718-57-8
• Molecular Formula: C16H24 B N O2
• Molecular Weight: 273.183
• DSSTox Substance ID: DTXSID40582875
• Wikidata: Q82474377
• Mol file: 922718-57-8.mol

Synonyms:922718-57-8;2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline;2-Methyl-1,2,3,4-tetrahydro-isoquinoline-6-boronic acid pinacol ester;2-Methyl-1,2,3,4-tetrahydroisoquinoline-6-boronic acid pinacol ester;2-METHYL-6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDRO-1H-ISOQUINOLINE;1,2,3,4-TETRAHYDRO-2-METHYL-6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-ISOQUINOLINE;SCHEMBL586404;DTXSID40582875;XLB71857;MFCD11044665;SB39952;BS-24799;SY040981;CS-0131457;G18852

Chemical Property of 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

• Vapor Pressure: 1.1E-05mmHg at 25°C
• Boiling Point: 370.5oC at 760 mmHg
• Flash Point: 177.9oC
• PSA: 21.70000
• Density: 1.06g/cm3
• LogP: 1.91160
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 273.1900092
• Heavy Atom Count: 20
• Complexity: 356

Purity/Quality:

97% ^*data from raw suppliers

2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(CN(CC3)C)C=C2

Technology Process of 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline

There total 10 articles about 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline 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: 49.0%

→ 2-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (922718-57-8)

Guidance literature:

Reference yield: 42.0%

2-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl trifluoromethanesulfonate + bis(pinacol)diborane (73183-34-3) → 2-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (922718-57-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 ℃; for 18h; Inert atmosphere;

DOI:10.1039/c4md00280f

Reference yield:

6-bromo-2-methyl-1,2,3,4-tetrahydroisoquinoline (59961-00-1) + bis(pinacol)diborane (73183-34-3) → 2-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (922718-57-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 25 - 90 ℃; for 14h; Inert atmosphere;

upstream raw materials:

2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinolinium; iodide

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline

6-bromo-isoquinoline

bis(pinacol)diborane

Downstream raw materials:

C₃₃H₃₅N₅O₄