2-(Dimethylamino)phenylboronic acid

Base Information

• Chemical Name: 2-(Dimethylamino)phenylboronic acid
• CAS No.: 89291-23-6
• Molecular Formula: C8H12 B N O2
• Molecular Weight: 165
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID60402561
• Nikkaji Number: J3.406.237D
• Wikidata: Q82205987
• Mol file: 89291-23-6.mol

Synonyms:89291-23-6;2-(DIMETHYLAMINO)PHENYLBORONIC ACID;2-(Dimethylamine)phenylboronic acid;[2-(dimethylamino)phenyl]boronic acid;2-Dimethylaminophenylboronic acid;2-(Dimethylamino)phenylboronicAcid;(2-(Dimethylamino)phenyl)boronic acid;MFCD01318997;Boronic acid, [2-(dimethylamino)phenyl]-;SCHEMBL27870;DTXSID60402561;NLTUDNKQUJVGKP-UHFFFAOYSA-N;AMY32842;N,N-dimethylaminobenzeneboronic acid;(2-(Dimethylamino)phenyl)boronicacid;AC1046;AKOS003585311;AB08809;GS-6183;NCGC00249505-01;CS-0176064;FT-0750565;EN300-251015;A857408;J-506384

Chemical Property of 2-(Dimethylamino)phenylboronic acid

Chemical Property:

• Vapor Pressure: 0.000166mmHg at 25°C
• Melting Point: 70 °C
• Refractive Index: 1.547
• Boiling Point: 317°C at 760 mmHg
• PKA: 8.86±0.58(Predicted)
• Flash Point: 145.5°C
• PSA: 43.70000
• Density: 1.12g/cm³
• LogP: -0.56760
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.0961088
• Heavy Atom Count: 12
• Complexity: 141

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(Dimethylamino)phenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1N(C)C)(O)O
• Uses: 2-(Dimethylamino)phenylboronic acid

Technology Process of 2-(Dimethylamino)phenylboronic acid

There total 6 articles about 2-(Dimethylamino)phenylboronic acid 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: 91.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-bromo-N,N-dimethylaniline (698-00-0) → 2-(N,N-dimethylamino)phenylboronic acid (89291-23-6)

Guidance literature:

2-bromo-N,N-dimethylaniline; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h;

Trimethyl borate; In tetrahydrofuran; for 2h;

Reference yield: 77.0%

Triisopropyl borate (5419-55-6) + 2-bromo-N,N-dimethylaniline (698-00-0) + water (7732-18-5) → 2-(N,N-dimethylamino)phenylboronic acid (89291-23-6)

Guidance literature:

2-bromo-N,N-dimethylaniline; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

water;

DOI:10.1002/anie.201708578

Reference yield: 45.0%

Trimethyl borate (121-43-7,63156-11-6) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → 2-(N,N-dimethylamino)phenylboronic acid (89291-23-6)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; hexane; addn. of 2 equiv. BuLi (in hexane) to amine and TMEDA (1 equiv.) in Et2O, stirring and refluxing (2 h), slow mixing with B(OMe)3 in Et2O (<-60°C, <1 h), slow warming to room temp. (during 24 h); water addn., pH-adjustment to 11, sepn. of aq. layer, pH-adjustment to 8, extn. (CHCl3), drying of extract, concn., recrystn. (hexane); elem. anal.;

DOI:10.1016/S0022-328X(00)99290-8

upstream raw materials:

Trimethyl borate

N,N-dimethyl-aniline

2-bromo-N,N-dimethylaniline

2-(N,N-dimethylamino)phenylboronic acid dimethyl ester

Downstream raw materials:

2'-bromo-N,N-dimethyl-[1,1'-biphenyl]-2-amine

1-(4-(2-(dimethylamino)phenyl)thiazol-2-yl)piperidine-4-carboxamide trifluoroacetate

C₂₈H₂₅N₃O₄

Refernces

• 1、 Jayaraman, Arumugam,Misal Castro, Luis C.,Fontaine, Frédéric-Georges. "Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts". supporting information. p. 1489 - 1499. Retrieved 2018/10/26.
• 2、 Colobert, Francoise,Valdivia, Victoria,Choppin, Sabine,Leroux, Frederic R.,Fernandez, Inmaculada,Alvarez, Eleuterio,Khiar, Noureddine. "Axial chirality control during suzuki-miyaura cross-coupling reactions: The tert-Butylsulfinyl group as an efficient chiral auxiliary". supporting information; experimental part. p. 5130 - 5133. Retrieved 2009/12/28.