1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Base Information

• Chemical Name: 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 837392-62-8
• Molecular Formula: C15H20BNO2
• Molecular Weight: 257.14
• Hs Code.: 2934999090
• European Community (EC) Number: 894-053-4
• DSSTox Substance ID: DTXSID80584555
• Nikkaji Number: J2.334.418A
• Wikidata: Q72491883
• Mol file: 837392-62-8.mol

Synonyms:837392-62-8;1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1-Methylindole-5-boronic acid pinacol ester;1-Methylindole-5-boronic acid, pinacol ester;1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole;MFCD05663865;1-Methyl-5-indoleboronic acid pinacol ester;N-methylindole-5-boronic acid pinacol ester;SCHEMBL484221;DTXSID80584555;JQLYKUPEQYNDFF-UHFFFAOYSA-N;BCP32947;AKOS004114854;AB21975;AM87226;CS-W021356;DS-13512;SY014930;1-Methyl-5-indolylboronic acid, pinacol ester;EN300-212562;1-Methyl-1H-indole-5-boronic acid pinacol ester;1-Methylindole-5-boronic acid pinacol ester, 97%;A849892;1-METHYLINDOLE-5-BORONIC ACID,PINACOL ESTER;J-504961;Z2044774134;(1-METHYL-1H-INDOL-5-YL)BORONIC ACID PINACOL ESTER;1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1-Methyl-5-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)-1H-indole

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 110-114 °C(lit.)
• Refractive Index: 1.534
• 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.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 257.1587090
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N(C=C3)C

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

There total 21 articles about 1-Methyl-5-(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: 80.0%

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline (934570-43-1) → 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (837392-62-8)

Guidance literature:

With N,N'-bis(salicylidene)-1,2-phenylene diaminocobalt(II); [Ru(1,10-phenanthroline-5,6-dione)₃](PF₆)₂; oxygen; In methanol; at 65 ℃; for 6h; under 760.051 Torr; Reagent/catalyst; Temperature; Solvent; Catalytic behavior;

DOI:10.1021/acs.orglett.9b00111

Reference yield: 78.0%

5-bromo-1-methyl-H-indole (10075-52-2) + 4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (837392-62-8)

Guidance literature:

With triethylamine; palladium diacetate; CyJohnPhos; In 1,4-dioxane; at 80 ℃;

DOI:10.1002/hlca.200690097

Reference yield: 78.0%

5-bromo-1-methyl-H-indole (10075-52-2) + dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8) → 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (837392-62-8)

Guidance literature:

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane; With potassium methanolate; In 1,2-dimethoxyethane; at 30 ℃; for 0.166667h; Inert atmosphere;

5-bromo-1-methyl-H-indole; In 1,2-dimethoxyethane; at 30 ℃; for 1h;

DOI:10.1021/ja309578k

upstream raw materials:

5-bromo-1-methyl-H-indole

5-bromo-1H-indole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

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

Downstream raw materials:

1-methyl-5-(trifluoromethyl)-1H-indole

1,5-dimethyl-1H-indole

(1-methyl-1H-indol-5-yl)boronic acid

Refernces

• 1、 Cid, M. B.,Díaz, Cristina,Franco, Mario,Lamsabhi, Al Mokhtar,Sainz, Raquel,Tortosa, Mariola. "Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions". . p. 3501 - 3513. Retrieved 2021/06/06.
• 2、 Niu, Yi-Jie,Sui, Guo-Hui,Zheng, Hong-Xing,Shan, Xiang-Huan,Tie, Lin,Fu, Jia-Le,Qu, Jian-Ping,Kang, Yan-Biao. "Competing dehalogenation versus borylation of aryl iodides and bromides under transition-metal-free basic conditions". . p. 10805 - 10813. Retrieved 2019/09/30.