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

Base Information

• Chemical Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 922718-55-6
• Molecular Formula: C₁₅H₂₂BNO₂
• Molecular Weight: 259.156
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80582874
• Wikidata: Q82474375
• Mol file: 922718-55-6.mol

Synonyms:922718-55-6;6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline;1,2,3,4-TETRAHYDRO-6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-ISOQUINOLINE;DTXSID80582874;1,2,3,4-Tetrahydro-isoquinoline-6-boronic acid pinacol ester;MFCD11044666;AS-83359;CS-0175649;1-(di(aziridin-1-yl)phosphoryl)-3-phenylurea;EN300-1609398;1,2,3,4-Tetrahydroisoquinoline-6-boronic acid pinacol ester;6-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,2,3,4-TETRAHYDROISOQUINOLINE

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

Chemical Property:

• Vapor Pressure: 5.37E-06mmHg at 25°C
• Boiling Point: 380.6oC at 760 mmHg
• Flash Point: 184oC
• PSA: 30.49000
• Density: 1.07g/cm3
• LogP: 1.96030
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 259.1743591
• Heavy Atom Count: 19
• Complexity: 329

Purity/Quality:

98.5% ^*data from raw suppliers

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride 95+% ^*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(CNCC3)C=C2

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

There total 4 articles about 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:

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline (675576-26-8) → 6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (922718-55-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; at 20 ℃; for 24h;

DOI:10.1021/jm060844e

Reference yield:

6-bromo-isoquinoline (34784-05-9) → 6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (922718-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / KOAc / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide / 17 h / 80 °C

2: H₂ / PtO₂ / ethanol / 24 h / 20 °C

With hydrogen; potassium acetate; platinum(IV) oxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm060844e

Reference yield:

bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (922718-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / KOAc / PdCl₂(dppf)*CH₂Cl₂ / dimethylformamide / 17 h / 80 °C

2: H₂ / PtO₂ / ethanol / 24 h / 20 °C

With hydrogen; potassium acetate; platinum(IV) oxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm060844e

upstream raw materials:

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

6-bromo-isoquinoline

bis(pinacol)diborane

Refernces

• 1、 Wang, Qiuping,Lucien, Edlaine,Hashimoto, Akihiro,Pais, Godwin C. G.,Nelson, David M.,Song, Yongsheng,Thanassi, Jane A.,Marlor, Christopher W.,Thoma, Christy L.,Cheng, Jijun,Podos, Steven D.,Ou, Yangsi,Deshpande, Milind,Pucci, Michael J.,Buechter, Douglas D.,Bradbury, Barton J.,Wiles, Jason A.. "Isothiazoloquinolones with enhanced antistaphylococcal activities against multidrug-resistant strains: Effects of structural modifications at the 6-, 7-, and 8-positions". . p. 199 - 210. Retrieved 2007/10/03.