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

Base Information

• Chemical Name: N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 171364-78-6
• Molecular Formula: C14H22BNO2
• Molecular Weight: 247.145
• Hs Code.: 2934999090
• European Community (EC) Number: 675-013-3
• DSSTox Substance ID: DTXSID60374436
• Nikkaji Number: J902.926E
• Wikidata: Q82163031
• Mol file: 171364-78-6.mol

Synonyms:171364-78-6;N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;4-(n,n-dimethylamino)phenylboronic acid, pinacol ester;4-(n,n-dimethylamino)phenylboronic acid pinacol ester;4-(Dimethylamino)phenylboronic Acid Pinacol Ester;dimethyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine;MFCD05663854;4-(N,N-Dimethylamino)phenylboronic acid, pinacol ester, AldrichCPR;4-(n,n-dimethylamino)phenylboronic acid,pinacol ester;HEXOXYETHYLACRYLATE;SCHEMBL30520;(4-(DIMETHYLAMINO)PHENYL)BORONIC ACID PINACOL ESTER;DTXSID60374436;DGMLJJIUOFKPKB-UHFFFAOYSA-N;2-[4-(Dimethylamino)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;AKOS015950766;AB21959;CS-W000881;DS-14796;SY026623;D3832;EN300-1425786;A811321;J-010714;Z1336745082;N,N-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;2-[4-(Dimethylamino)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborole;Dimethyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl)phenyl]amine

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

Chemical Property:

• Vapor Pressure: 5.49E-05mmHg at 25°C
• Melting Point: 122-123 °C
• Refractive Index: 1.506
• Boiling Point: 347.1 °C at 760 mmHg
• PKA: 4.66±0.24(Predicted)
• Flash Point: 163.7 °C
• PSA: 21.70000
• Density: 1.01 g/cm³
• LogP: 2.05180
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 247.1743591
• Heavy Atom Count: 18
• Complexity: 280

Purity/Quality:

98% ^*data from raw suppliers

4-(N,N-Dimethylamino)phenylboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

Useful:

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

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

There total 47 articles about N,N-dimethyl-4-(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: 99.7%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-(dimethylamino)benzene-boronic acid (28611-39-4) → (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-78-6)

Guidance literature:

In dichloromethane; for 15h;

DOI:10.1016/j.tetlet.2012.11.001

Reference yield: 96.0%

4-bromo-N,N-dimethylaniline (586-77-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-78-6)

Guidance literature:

With palladium diacetate; triethylamine; bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; 1,4-dioxane; at 100 ℃; for 3h;

DOI:10.1021/ol048303b

Reference yield: 91.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4-bromo-N,N-dimethylaniline (586-77-6) → (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-78-6)

Guidance literature:

4-bromo-N,N-dimethylaniline; With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; for 0.75h;

DOI:10.1021/ja513027s

upstream raw materials:

4-bromo-N,N-dimethylaniline

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

4-chloro-N,N-dimethylaniline

bis(pinacol)diborane

Downstream raw materials:

Zn(C₂₀H₈N₄(C₆H₄N(CH₃)2)2(C₆H₃(C(CH₃)3)2)2)

C₂₅H₂₄N₄O₂S

7-(4-N,N-dimethylaminophenyl)-2-(4-cyanophenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile

4’-(dimethylamino)-[1,1’-biphenyl]-4-carbaldehyde

Refernces

• 1、 Broutin, Pierre-Emmanuel,Cerna, Igor,Campaniello, Maria,Leroux, Frederic,Colobert, Francoise. "Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis". . p. 4419 - 4422. Retrieved 2004.
• 2、 Appukkuttan, Prasad,Van Der Eycken, Erik,Dehaen, Wim. "Microwave enhanced formation of electron rich arylboronates". . p. 1204 - 1206. Retrieved 2003.
• 3、 Barroso, Santiago,Joksch, Markus,Puylaert, Pim,Tin, Sergey,Bell, Stephen J.,Donnellan, Luke,Duguid, Stewart,Muir, Colin,Zhao, Peichao,Farina, Vittorio,Tran, Duc N.,De Vries, Johannes G.. "Improvement in the Palladium-Catalyzed Miyaura Borylation Reaction by Optimization of the Base: Scope and Mechanistic Study". . p. 103 - 109. Retrieved 2021.
• 4、 Deng, Xi,Guo, Jiandong,Su, Weiping,Wang, Xiaotai,Zhang, Xiaofeng. "Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel-Catalyzed Direct Decarbonylative Borylation". . p. 24510 - 24518. Retrieved 2021/08/12.
• 5、 Pein, Wesley L.,Wiensch, Eric M.,Montgomery, John. "Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation". supporting information. . Retrieved 2021/06/28.