4-(Dimethylamino)phenylboronic acid

Base Information

• Chemical Name: 4-(Dimethylamino)phenylboronic acid
• CAS No.: 28611-39-4
• Molecular Formula: C8H12BNO2
• Molecular Weight: 165
• Hs Code.: 29319090
• European Community (EC) Number: 628-766-7
• DSSTox Substance ID: DTXSID00370235
• Nikkaji Number: J995.315I
• Wikidata: Q72469133
• Mol file: 28611-39-4.mol

Synonyms:4-(Dimethylamino)phenylboronic acid;28611-39-4;(4-(Dimethylamino)phenyl)boronic acid;4-(N,N-Dimethylamino)phenylboronic acid;[4-(dimethylamino)phenyl]boronic acid;4-Dimethylaminophenylboronic acid;4-(Dimethylamino)benzeneboronic acid;BORONIC ACID, B-[4-(DIMETHYLAMINO)PHENYL]-;MFCD01074642;4-Dimethylaminophenylboronic acid HCl;(4-dimethylaminophenyl)boronic Acid;4-dimethylaminophenyl boronic acid;[4-(dimethylamino)phenyl]boranediol;4-DIMETHYLAMINOBENZENEBORONIC ACID;Boronic acid, [4-(dimethylamino)phenyl]-;SCHEMBL9369;DTXSID00370235;4-dimethylamino-phenylboronic acid;4-dimethylaminophenyl-boronic acid;RIIPFHVHLXPMHQ-UHFFFAOYSA-N;4-(Dimethylamino)phenylboronicacid;4-dimethylaminobenzene boronic acid;4-dimethylamino-phenyl boronic acid;4-dimethylamino-phenyl-boronic acid;4-(dimethylamino)-phenylboronic acid;4-(dimethylamino)phenyl boronic acid;(4-dimethylamino-phenyl)-boronic acid;4-(dimethylamino)-phenyl boronic acid;AKOS004116213;AB08086;AM86834;PS-9486;4-N,N-DIMETHYLPHENYLBORONIC ACID;(4-(dimethylamino)-phenyl)-boronic acid;4-(n,n-dimethylamino)benzeneboronic acid;NCGC00249469-01;NCGC00249469-02;4-(n,n-dimethylamino) phenylboronic acid;4-(N,N-dimethylamino)phenyl boronic acid;AC-16575;AC-33457;BP-11353;N,N-dimethyl-4-amino-phenyl boronic acid;SY020954;A5411;CS-0007624;D4428;FT-0616828;4-(Dimethylamino)phenylboronic acid, >=95.0%;EN300-310445;[2-(4-Aminophenyl)ethyl]carbamicacidtert-butylester;J-017157;F8882-1126

Chemical Property of 4-(Dimethylamino)phenylboronic acid

Chemical Property:

• Appearance/Colour: white to green-grey or blue-grey crystalline
• Vapor Pressure: 6.92E-05mmHg at 25°C
• Melting Point: 227 °C(lit.)
• Refractive Index: 1.547
• Boiling Point: 329.9 °C at 760 mmHg
• PKA: 8.78±0.10(Predicted)
• Flash Point: 153.3 °C
• PSA: 43.70000
• Density: 1.12 g/cm³
• LogP: -0.56760
• Storage Temp.: 0-6°C
• Water Solubility.: Sparingly soluble in water. (~2.5%)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.0961088
• Heavy Atom Count: 12
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

4-(Dimethylamino)phenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)N(C)C)(O)O
• Uses: suzuki reaction 4-(Dimethylamino)phenylboronic Acid can be used as reactant/reagent in preparation of biaryls via palladium-catalyzed Suzuki-Miyaura coupling of nitroarenes with boronic acids.

Technology Process of 4-(Dimethylamino)phenylboronic acid

There total 11 articles about 4-(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: 90.0%

triethyl borate (150-46-9) + 4-bromo-N,N-dimethylaniline (586-77-6) → 4-(dimethylamino)benzene-boronic acid (28611-39-4)

Guidance literature:

4-bromo-N,N-dimethylaniline; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique;

triethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1441h; Inert atmosphere; Schlenk technique;

With hydrogenchloride; In tetrahydrofuran; hexane; water; for 2h;

DOI:10.1002/chem.202003391

Reference yield: 85.0%

boric acid tributyl ester (688-74-4) + water (7732-18-5) + 4-dimethylaminophenylmagnesium bromide (7353-91-5) → 4-(dimethylamino)benzene-boronic acid (28611-39-4)

Guidance literature:

In tetrahydrofuran; react. at -65°C, 12h at room temp., hydrolysis with H2O, addn. of dild. H2So4 until pH 3-4, extractn. with ether, neutralization of aq. and organic phase with NH3;; extractn. of impurities with petroleum ether;;

Reference yield: 82.0%

4-bromo-N,N-dimethylaniline (586-77-6) → 4-(dimethylamino)benzene-boronic acid (28611-39-4)

Guidance literature:

4-bromo-N,N-dimethylaniline; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; toluene; at 20 ℃; for 15h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol2016252

upstream raw materials:

boric acid tributyl ester

4-dimethylaminophenyllithium

4-bromo-N,N-dimethylaniline

water

Downstream raw materials:

5-(4-Dimethylamino-phenyl)-1-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione

4’-(4-N,N-dimethylaminophenyl)-2,2’:6’,2’’-terpyridine

Refernces

• 1、 Abe, Manabu,Chitose, Youhei,Lin, Tzu-Chau,Pham, Thuy Thi Thu,Tam, Tran Thi Thanh,Tseng, Wei-Lun. "Impact of Five-membered Heterocyclic Rings on Photophysical Properties including Two-photon Absorption Character". supporting information. p. 1810 - 1813. Retrieved 2021/10/27.
• 2、 -. "Benzacridine derivatives and organic light-emitting device (OLED) thereof". Paragraph 0057; 0058; 0059. . Retrieved 2018/07/30.