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

Base Information

• Chemical Name: 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 898289-06-0
• Molecular Formula: C₁₅H₂₀BNO₂
• Molecular Weight: 257.14
• Hs Code.: 2934999090
• European Community (EC) Number: 893-880-8
• DSSTox Substance ID: DTXSID10594541
• Nikkaji Number: J2.334.415G
• Wikidata: Q82489414
• Mol file: 898289-06-0.mol

Synonyms:898289-06-0;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1-Methy-1H-indol-4-ylboronic acid pinacol ester;1-Methylindol-4-boronic acid, pinacol ester;1-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)INDOLE;1H-Indole, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;1-methylindol-4-boronic acid pinacol ester;SCHEMBL2216834;DTXSID10594541;CBEYYYCGOCYJIK-UHFFFAOYSA-N;(1-METHYL-1H-INDOL-4-YL)BORONIC ACID PINACOL ESTER;MFCD08690266;1H-Indole,1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;AKOS016000327;FS-6016;SB39701;DB-078500;CS-0138029;EN300-6739225;1-Methyl-1H-indole-4-boronic acid, pinacol ester;A861048;J-504938;Z2050045918;1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole;1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, AldrichCPR

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

Chemical Property:

• Vapor Pressure: 5.6E-06mmHg at 25°C
• Melting Point: 94.5-96.5
• Boiling Point: 391.3°C at 760 mmHg
• Flash Point: 190.5°C
• PSA: 23.39000
• Density: 1.05g/cm³
• LogP: 2.47750
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°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:

98%min ^*data from raw suppliers

1-Methylindol-4-boronic acid pinacol ester ^*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=C3C=CN(C3=CC=C2)C

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

There total 10 articles about 1-Methyl-4-(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: 87.0%

C20H29BN2O4 (1379516-33-2) → 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (898289-06-0)

Guidance literature:

With bis(tricyclohexylphosphine)nickel(II) dichloride; 1,1,3,3-Tetramethyldisiloxane; K₃PO₄; In toluene; at 120 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ol301275u

Reference yield: 79.0%

4-bromo-1-methyl-1H-indole (590417-55-3) + 4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (898289-06-0)

Guidance literature:

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

DOI:10.1002/hlca.200690097

Reference yield: 79.0%

4-bromo-1-methyl-1H-indole (590417-55-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (898289-06-0)

Guidance literature:

With palladium diacetate; triethylamine; In 1,4-dioxane; under Ar atm.; Schlenk flask charged with Pd(CH3COO)2 and P(C6H11)2(C6H4C6H5); evapd.; filled (Ar); 1,4-dioxane added; stirred for 30 min at room temp.; Et3N added; soln. of bromoindole in dioxane added; neat pinacolborane added; stirred at 80°C; cooled to room temp.; Celite and activated charcoal added; stirred for 15 min; filtered; solvent removed (vac.); residue diluted (cyclohexane); filtered through a short pad of neutral alumina; purified by column chromy (SiO2, cyclohexane/ethyl acetate);

DOI:10.1002/hlca.200690097

upstream raw materials:

4-bromo-1-methyl-1H-indole

4-bromo-1H-indole

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

diethyl-carbamic acid 1-methyl-1H-indol-5-yl ester

Refernces

• 1、 -. "SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE". . . Retrieved 2019/01/21.
• 2、 -. "SUBSTITUTED QUINOXALINE DERIVATIVES". Page/Page column 196; 212. . Retrieved 2016/12/01.