N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Base Information

• Chemical Name: N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
• CAS No.: 214360-57-3
• Molecular Formula: C14H20 B N O3
• Molecular Weight: 261.129
• Hs Code.: 2931900090
• European Community (EC) Number: 805-088-1
• DSSTox Substance ID: DTXSID80590398
• Wikidata: Q82484102
• Mol file: 214360-57-3.mol

Synonyms:214360-57-3;N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide;4-(N-Methylaminocarbonyl)phenylboronic acid, pinacol ester;4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER;4-(N-Methylaminocarbonyl)phenylboronic acid pinacol ester;BENZAMIDE, N-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;4-N-Methylcarboxamidophenylboronic acid, pinacol ester, AldrichCPR;SCHEMBL419695;DTXSID80590398;AICMMMQOGJNFFG-UHFFFAOYSA-N;(4-(METHYLCARBAMOYL)PHENYL)BORONIC ACID PINACOL ESTER;MFCD06795690;AKOS015960119;AB29269;AS-2476;SY006671;CS-0041345;EN300-6740656;A879101;4-(Methylcarbamoyl)benzeneboronic Acid Pinacol Ester;J-014063;4-N-Methylcarboxamidophenylboronic acid,pinacol ester;Z2050052869;N-METHYL-4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZAMIDE;N-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 407.6°Cat760mmHg
• Flash Point: 200.3°C
• PSA: 47.56000
• Density: 1.07g/cm³
• LogP: 1.73630
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 261.1536237
• Heavy Atom Count: 19
• Complexity: 333

Purity/Quality:

97% ^*data from raw suppliers

4-N-Methylcarboxamidophenylboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C(=O)NC

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

There total 16 articles about N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide 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: 94.0%

N-methylbenzamide (88070-48-8) + bis(pinacol)diborane (73183-34-3) → N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzamide (214360-57-3) + N-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (1197171-76-8) + N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N-(2,3-dimethyl-1H-indol-7-yl)-[2,2'-bipyridine]-5-carboxamide; In tetrahydrofuran; at 50 ℃; for 24h; regioselective reaction; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201907366

Reference yield: 91.0%

4-bromo-N-methylbenzamide (27466-83-7) + bis(pinacol)diborane (73183-34-3) → N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzamide (214360-57-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃;

Reference yield: 80.0%

bis(pinacol)diborane (73183-34-3) → N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzamide (214360-57-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

DOI:10.1002/anie.201907366

upstream raw materials:

methylamine

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid chloride

4-bromo-N-methylbenzamide

bis(pinacol)diborane

Downstream raw materials:

4-{6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl}-N-methyl-benzamide

C₃₆H₂₃F₃N₄O₂

2'-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-N-methylbiphenyl-4-carboxamide

C₂₅H₂₅N₃OS

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