4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

Base Information

• Chemical Name: 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone
• CAS No.: 1360607-18-6
• Molecular Formula: C₁₆H₂₅BN₂O₃
• Molecular Weight: 304.197
• Mol file: 1360607-18-6.mol

Synonyms:4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

Chemical Property of 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone

There total 3 articles about 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone 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: 77.0%

4-methoxybenzaldehyde dimethylhydrazone (14371-13-2) + bis(pinacol)diborane (73183-34-3) → 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone (1360607-18-6)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N,N-dibenzyl-N'-(pyridin-2-ylmethylene)hydrazine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 80 ℃; for 10h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201104544

Reference yield: 77.0%

4-methoxybenzaldehyde dimethylhydrazone (14371-13-2) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone (1360607-18-6)

Guidance literature:

With cat. [Ir(μ-OCH3)(C8H12)]2/2-C5H4NCHNN(CH2C6H5)2; In tetrahydrofuran; Sonication; dried Schlenk tube charged with dimethylhydrazone and diboron compd., added catalyst stock soln. (prepd. by sonication for 1 h) and pinacolborane, stirred at 80°C for 10 h; cooled to room temp., concd. to dryness, purified by column chromy. on neutral alumina (n-hexane/CH3COOC2H5);

DOI:10.1002/anie.201104544

Reference yield:

4-methoxybenzaldehyde dimethylhydrazone (14371-13-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde N,N-dimethylhydrazone (1360607-18-6)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4-(dimethylamino)picolinaldehyde N,N-dibenzylhydrazone; In tetrahydrofuran; at 80 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo301965v

upstream raw materials:

4-methoxybenzaldehyde dimethylhydrazone

bis(pinacol)diborane

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