9-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Base Information

• Chemical Name: 9-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
• CAS No.: 1217891-71-8
• Molecular Formula: C19H22BNO2
• Molecular Weight: 307.19448
• Hs Code.: 2933990090
• Mol file: 1217891-71-8.mol

Synonyms:9-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole;N-Methylcarbazole-3-boronic acid pinacol ester;9-Methyl-9H-carbazole-3-boronic acid pinacol ester

Chemical Property of 9-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Chemical Property:

• Melting Point: 146-151°C
• PSA: 23.39000
• LogP: 3.63070

Purity/Quality:

97% ^*data from raw suppliers

9-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 52/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

There total 12 articles about 9-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 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: 76.0%

N-methylcarbazole (1484-12-4) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 9-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole (1217891-71-8)

Guidance literature:

N-methylcarbazole; With boron trichloride; Dimethyl-p-toluidine; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With triethylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

Reference yield: 76.0%

N-methylcarbazole (1484-12-4) + 2,3-dimethyl-2,3-butane diol (76-09-5) + boron trichloride (10294-34-5) → 9-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole (1217891-71-8)

Guidance literature:

With AlCl₃; 2,6-lutidine; In dichloromethane; 1:1 mixt. of BCl3 and AlCl, pinacol (2.3-3.0 equiv.) and lutidine (15 equiv.) for 14 h;

DOI:10.1039/c1cc14226g

Reference yield: 71.0%

N-methylcarbazole (1484-12-4) + 2,3-dimethyl-2,3-butane diol (76-09-5) + C6Cl4O2BN(C2H5)3(1+)*AlCl4(1-)=C6Cl4O2BN(C2H5)3[AlCl4] → 9-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole (1217891-71-8)

Guidance literature:

With Et₃N; In dichloromethane; byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added Cl4CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excessEt3N added; pinacol added; stirred for 24 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;;

DOI:10.1002/anie.201006196

upstream raw materials:

2,3-dimethyl-2,3-butane diol

N-methylcarbazole

boron trichloride

9H-carbazole