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

Base Information

• Chemical Name: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 191171-55-8
• Molecular Formula: C12H18BNO2
• Molecular Weight: 219.091
• Hs Code.: 29310099
• European Community (EC) Number: 626-344-7
• DSSTox Substance ID: DTXSID50370422
• Nikkaji Number: J1.486.110F
• Wikidata: Q72440503
• Mol file: 191171-55-8.mol

Synonyms:191171-55-8;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;2-Aminophenylboronic acid pinacol ester;2-aminophenylboronic acid, pinacol ester;MFCD02179448;2-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;(2-aminophenyl)boronic acid pinacol ester;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine;Benzenamine, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-aminobenzeneboronic acid pinacol ester;2-(2-AMINOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;SCHEMBL168780;DTXSID50370422;ZCJRWQDZPIIYLM-UHFFFAOYSA-N;2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine;BCP14683;CS-D0918;AKOS005256282;AB11148;AM62751;AS-3013;2-amino-phenylboronic acid pinacol ester;2-aminophenyl boronic acid pinacol ester;AC-33505;SY008061;(2-aminophenyl)boronic acid, pinacol ester;A4219;FT-0643806;T3543;EN300-195188;J-505874;2-(2-aminophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline;2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-aniline;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)aniline;2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine;2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-BENZENAMINE

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

Chemical Property:

• Appearance/Colour: cream crystalline powder
• Vapor Pressure: 0.000118mmHg at 25°C
• Melting Point: 63-68 °C(lit.)
• Refractive Index: 1.516
• Boiling Point: 335.6 °C at 760 mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: 156.8 °C
• PSA: 44.48000
• Density: 1.05 g/cm³
• LogP: 2.14920
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 219.1430590
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

99% ^*data from raw suppliers

2-Aminophenylboronic acid pinacol cyclic ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2N
• Uses: Reactant involved in synthesis of: Indolo[3,4-cd]benzazepines via Pictet-Spengler-type cyclizations Antimicrobial amphiphilic aryl peptideomimetics Pyridoquinazolines and benzo[h] naphthyridines via intramolecular electrophilic substitution reaction Reactant involved in synthesis of:Indolo[3,4-cd][1]benzazepines via Pictet-Spengler-type cyclizationsAntimicrobial amphiphilic aryl peptideomimeticsPyridoquinazolines and benzo[h][1,6]naphthyridines via intramolecular electrophilic substitution reactionsThienopyridine derivativesDihydroquinolonesMethacrylamidophenylboronic acids

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

There total 30 articles about 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: 98.0%

2-bromoaniline (615-36-1) + bis(pinacol)diborane (73183-34-3) → 2-anilineboronic acid pinacol ester (191171-55-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; for 12h; Reflux;

Reference yield: 95.8%

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (190788-59-1) → 2-anilineboronic acid pinacol ester (191171-55-8)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 80 ℃; for 4h; Temperature; Solvent; Inert atmosphere;

Reference yield: 95.0%

2-iodophenylamine (615-43-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-anilineboronic acid pinacol ester (191171-55-8)

Guidance literature:

With dichlorobis(chlorodi-tert-butylphosphine) palladium(II); triethylamine; In toluene; for 2h; Inert atmosphere; Reflux;

DOI:10.2478/s11532-010-0076-1

upstream raw materials:

o-chloroaniline

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

2-bromoaniline

2,3-dimethyl-2,3-butane diol

Downstream raw materials:

methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-acetate

2-N-acryloylaminophenylboronic acid pinacol ester

methyl (+/-)-1-(2-aminophenyl)-8-ethyl-3-formyl-5,6,7,8-tetrahydroindolizin-8-propionate

2-(2-pyridyl)aniline