3-methyl-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Base Information

• Chemical Name: 3-methyl-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 651014-84-5
• Molecular Formula: C19H24BNO2
• Molecular Weight: 309.216
• DSSTox Substance ID: DTXSID90438696
• Nikkaji Number: J2.304.925B
• Wikidata: Q82254508
• Mol file: 651014-84-5.mol

Synonyms:651014-84-5;3-methyl-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;3-Methyl-N-phenyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline;starbld0019393;DTXSID90438696;2-[3-(Phenylamino)-5-methylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 3-methyl-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 309.1900092
• Heavy Atom Count: 23
• Complexity: 390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)NC3=CC=CC=C3)C

Technology Process of 3-methyl-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

There total 8 articles about 3-methyl-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 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: 79.0%

aniline (62-53-3) + 2-(3-chloro-5-methylphenyl)-4,4,5,5-tetra methyl-1,3,2-dioxaborolane (502630-89-9) → N-phenyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (651014-84-5)

Guidance literature:

With potassium phosphate; tri-tert-butyl phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,2-dimethoxyethane; at 100 ℃; for 18h;

DOI:10.1021/ol060205y

Reference yield: 75.0%

1-chloro-3-methylbenzene (108-41-8) + aniline (62-53-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → N-phenyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (651014-84-5)

Guidance literature:

1-chloro-3-methylbenzene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With 1,2-bis(dimethylphosphanyl)ethane; (η⁵-indenyl)(η⁴-1,5-cyclooctadiene)iridium(I); at 150 ℃; for 8h;

aniline; With potassium phosphate; tri-tert-butyl phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,2-dimethoxyethane; at 100 ℃; for 19h;

DOI:10.1021/ol060205y

Reference yield: 74.8%

meta-bromotoluene (591-17-3) + aniline (62-53-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → N-phenyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (651014-84-5)

Guidance literature:

meta-bromotoluene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; (η⁵-indenyl)(η⁴-1,5-cyclooctadiene)iridium(I); 1,2-bis(dimethylphosphanyl)ethane; at 150 ℃; for 17h;

aniline; With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; In 1,2-dimethoxyethane; at 100 ℃; for 19h;

upstream raw materials:

1-chloro-3-methylbenzene

aniline

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

meta-bromotoluene