1-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

Base Information

• Chemical Name: 1-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE
• CAS No.: 683229-61-0
• Molecular Formula: C15H20BNO2
• Molecular Weight: 257.14
• Hs Code.: 2934999090
• Mol file: 683229-61-0.mol

Synonyms:N-Methylindole-3-boronic acid pinacol ester;

Chemical Property of 1-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

Chemical Property:

• Boiling Point: 391.324 °C at 760 mmHg
• Flash Point: 190.466 °C
• PSA: 23.39000
• Density: 1.055 g/cm³
• LogP: 2.47750
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

There total 20 articles about 1-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE 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: 99.0%

1-methylindole (603-76-9) + C6H13BO2*C6H15N → 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (683229-61-0)

Guidance literature:

With 1-(trifluoroborato)-2-piperidinyl benzene; In neat (no solvent); at 80 ℃; for 6h; regioselective reaction; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.8b00248

Reference yield: 92.0%

1-methylindole (603-76-9) + 2,3-dimethyl-2,3-butane diol (76-09-5) + C6H4O2BN(C2H5)3(1+)*AlCl4(1-)=C6H4O2BN(C2H5)3[AlCl4] → 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (683229-61-0)

Guidance literature:

With Et₃N; In dichloromethane; byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excess Et3N added; pinacol added; stirred for 4 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;;

DOI:10.1002/anie.201006196

Reference yield: 87.0%

1-methylindole (603-76-9) + 2,3-dimethyl-2,3-butane diol (76-09-5) + 2-chloro-1,3,2-benzodioxaborole (55718-76-8) → 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (683229-61-0)

Guidance literature:

1-methylindole; 2-chloro-1,3,2-benzodioxaborole; With aluminum (III) chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With triethylamine; In dichloromethane; Irradiation;

upstream raw materials:

1-methylindole

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

boron trichloride

aluminium trichloride

Downstream raw materials:

9-methyl-9H-dibenzo[a,c]carbazole

1-methyl-1H-indole-3-carbonitrile

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