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

Base Information

• Chemical Name: 5-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 863578-36-3
• Molecular Formula: C13H20BNO2
• Molecular Weight: 233.118
• Hs Code.: 2934999090
• European Community (EC) Number: 690-888-1
• DSSTox Substance ID: DTXSID20590352
• Wikidata: Q82484070
• Mol file: 863578-36-3.mol

Synonyms:863578-36-3;2-AMINO-4-METHYLPHENYLBORONIC ACID, PINACOL ESTER;5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;2-Amino-4-methylphenylboronic acid pinacol ester;SCHEMBL771975;DTXSID20590352;PEXRISJTWBBZRY-UHFFFAOYSA-N;5-METHYL-2-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ANILINE;MFCD06795679;AKOS015960096;AB29240;AS-47849;CS-0140970;F16360;EN300-7390325;2-Amino-4-methylphenylboronic acid pinacol ester, AldrichCPR;1-NAPHTHALENECARBOXYLICACID,1,2,3,4-TETRAHYDRO-6-HYDROXY-;2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-methylphenylamine;5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine

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

Chemical Property:

• Vapor Pressure: 5.47E-05mmHg at 25°C
• Melting Point: 68 °C(Solv: hexane (110-54-3))
• Refractive Index: 1.515
• Boiling Point: 347.2 °C at 760 mmHg
• PKA: 4.02±0.11(Predicted)
• Flash Point: 163.8 °C
• PSA: 44.48000
• Density: 1.03 g/cm³
• LogP: 2.45760
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 233.1587090
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

2-Amino-4-methylphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=C(C=C2)C)N
• Uses: 2-Amino-4-methylphenylboronic acid, pinacol ester

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

There total 3 articles about 5-Methyl-2-(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: 84.0%

2-bromo-5-methylaniline (53078-85-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 5-methyl-2-(4,4,5,5-tetramethyl)(1,3,2-dioxaborolan-2-yl)phenylamine (863578-36-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In 1,4-dioxane; at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol5010615

Reference yield: 17.0%

2-bromo-5-methylaniline (53078-85-6) + bis(pinacol)diborane (73183-34-3) → 5-methyl-2-(4,4,5,5-tetramethyl)(1,3,2-dioxaborolan-2-yl)phenylamine (863578-36-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 110 ℃; for 6h;

Reference yield:

4-Bromo-3-nitrotoluene (5326-34-1) → 5-methyl-2-(4,4,5,5-tetramethyl)(1,3,2-dioxaborolan-2-yl)phenylamine (863578-36-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium chloride; zinc / 1,4-dioxane; water / 3 h / 20 °C

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 6 h / 110 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; ammonium chloride; zinc; In 1,4-dioxane; water; dimethyl sulfoxide;

upstream raw materials:

2-bromo-5-methylaniline

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

bis(pinacol)diborane

4-Bromo-3-nitrotoluene

Downstream raw materials:

4'-[3-(2-chloro-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-4-methyl-biphenyl-2-ylamine trifluoroacetic acid

5-methyl-2-(pyridin-2-yl)benzenamine

methyl 2,6-dimethylindole-3-carboxylate

2-azido-4-methylphenylboronic acid pinacolate ester