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

Base Information

• Chemical Name: 4-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 948592-80-1
• Molecular Formula: C13H20BNO2
• Molecular Weight: 233.118
• Hs Code.: 2931900090
• European Community (EC) Number: 689-858-0
• DSSTox Substance ID: DTXSID60590351
• Wikidata: Q82484068
• Mol file: 948592-80-1.mol

Synonyms:948592-80-1;2-AMINO-5-METHYLPHENYBORONIC ACID, PINACOL ESTER;4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;2-Amino-5-methylphenyboronic acid pinacol ester;4-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine;2-Amino-5-methylphenyboronic acid, pinacol ester, AldrichCPR;4-methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;SCHEMBL3191098;DTXSID60590351;LOOBNTHIWCHTCR-UHFFFAOYSA-N;MFCD06795664;AKOS015893487;AB29207;AS-55680;4-Methylaniline-2-boronic acid pinacol ester;CS-0037883;W16868;EN300-7390340;2-Amino-5-methylbenzeneboronic acid, pinacol ester;A845116

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

Chemical Property:

• Vapor Pressure: 3.08E-05mmHg at 25°C
• Boiling Point: 355.7°C at 760 mmHg
• PKA: 4.33±0.10(Predicted)
• Flash Point: 168.9°C
• PSA: 44.48000
• Density: 1.03g/cm³
• LogP: 2.45760
• Storage Temp.: under inert gas (nitrogen or Argon) at 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-5-methylphenyboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CC(=C2)C)N
• Uses: 2-Amino-5-methylphenyboronic acid, pinacol ester

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

There total 3 articles about 4-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: 94.0%

2-bromo-p-toluidine (583-68-6) + bis(pinacol)diborane (73183-34-3) → 4‐methyl‐2‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)aniline (948592-80-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 80 ℃; Inert atmosphere;

Reference yield: 89.0%

2-bromo-p-toluidine (583-68-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4‐methyl‐2‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)aniline (948592-80-1)

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: 63.0%

2-iodo-4-methylaniline (29289-13-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4‐methyl‐2‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)aniline (948592-80-1)

Guidance literature:

With N(CH₂CH₃)3; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; (Ar); addn. of triethylamine, palladium compd. and borane deriv. to dioxane soln. of aniline deriv., heating at 100°C for 5 h; cooling to room temp., filtration through celite with eluting by ethyl acetate, evapn., chromy. (silica gel, hexane/ethyl acetate (9/1 to 6/4)),NMR and MS;

DOI:10.1039/c2ob06695e

upstream raw materials:

2-bromo-p-toluidine

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

bis(pinacol)diborane

2-iodo-4-methylaniline

Downstream raw materials:

6-methyl-2-(1-methyl-pyrrol-2-yl)-4-(4-nitrophenyl)quinoline

2,4-diphenyl-6-methylquinoline

6-(2-amino-5-methylphenyl)-N,N-diethylpyridin-2-amine

2-(6-methoxypyridin-2-yl)-4-methylaniline