171364-78-6

Basic information

• Product Name: 4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: N,N-DIMETHYL[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]AMINE;DIMETHYL[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]AMINE;4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER;N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;2-[4-(Dimethylamino)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(Dimethylamino)phenylboronic Acid Pinacol Ester;N,N-DiMethyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)anil;2-[4-(Dimethylamino)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4-(Dimethylamino)phenylboronic Acid Pinacol Ester
• CAS NO: 171364-78-6
• Molecular Formula: C₁₄H₂₂BNO₂
• Molecular Weight: 247.14
• Mol File: 171364-78-6.mol
• Article Data: 71

Chemical Properties

• Melting Point: 122-123°C
• Boiling Point: 347.1 °C at 760 mmHg
• Flash Point: 163.7 °C
• Appearance: /
• Density: 1.01 g/cm³
• Vapor Pressure: 5.49E-05mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 4.66±0.24(Predicted)
• CAS DataBase Reference: 4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER(171364-78-6)
• EPA Substance Registry System: 4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER(171364-78-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37/39-36/37
• RIDADR: UN2811
• Hazardous Substances Data: 171364-78-6(Hazardous Substances Data)

Usage

General Description

4-(N,N-dimethylamino)phenylboronic acid, pinacol ester is a boronic acid derivative that is commonly used in organic synthesis as a reagent and building block. It contains a boronic acid functional group, which is known for its ability to form stable complexes with diols and other Lewis bases. The pinacol ester moiety provides increased stability and solubility in organic solvents, making it a versatile reagent for reactions such as Suzuki coupling, cross-coupling, and C-H bond activation. 4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER has found applications in the synthesis of pharmaceuticals, agrochemicals, and materials science, making it a valuable tool for chemists in various fields of research and development.

InChI:InChI=1/C14H22BNO2/c1-13(2)14(3,4)18-15(17-13)11-7-9-12(10-8-11)16(5)6/h7-10H,1-6H3

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 121-43-7 Trimethyl borate 
• 1369365-75-2 4-((tert-butyldimethylsilyl)oxy)-N,N-dimethylaniline 
• 73183-34-3 bis(pinacol)diborane 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 50-00-0 formaldehyd 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 108168-59-8 4-(dimethylamino)benzoyl fluoride 
• 403-46-3 4-fluoro-N,N-dimethylaniline 

Downstream Products

• 27104-67-2 4-(N,N-dimethylamino)-2'-carbonitrile-1,1'-biphenyl 
• 1187951-66-1 C₂₅H₂₄N₄O₂S 
• 112209-11-7 C₁₄H₈(C₆H₄N(CH₃)2)Br 
• 1448895-29-1 7-(4-N,N-dimethylaminophenyl)-2-(4-cyanophenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile 
• 173991-06-5 4’-(dimethylamino)-[1,1’-biphenyl]-4-carbaldehyde 
• 476004-80-5 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylthiophene 
• 214360-65-3 4-trifluoromethylphenylboronic acid pinacol ester 
• 2115706-15-3 C₃₇H₃₅N₃O₃ 

Relevant articles and documents

Novel Palladium(0)-Catalyzed Coupling Reaction of Dialkoxyborane with Aryl Halides: Convenient Synthetic Route to Arylboronates

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Electrochemical Radical Borylation of Aryl Iodides

Herein, we report the first electrochemical strategy for the borylation of aryl iodides via a radical pathway using current as a driving force. A mild reaction condition allows an assorted range of readily available aryl iodides to be proficiently converted into synthetically valuable arylboronic esters under transition metal catalyst-free conditions. Moreover, this method also shows good functional group tolerance. Initial control mechanistic experiments reveal the formation of aryl radical as a key intermediate and the current plays an important role in the generation of radical intermediate.

Cesium carbonate mediated borylation of aryl iodides with diboron in methanol

Herein we describe the unexpected borylation of aryl iodides promoted by a Cs2CO3 and MeOH system. This formal nucleophilic boryl substitution could be applied to a wide range of functionalized aryl iodide compounds. The preliminary results indicate that this process is neither copper catalyzed nor radical mediated. Copyright

Remote steric control for undirected meta-selective C-H activation of arenes

Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation

The conversion of silyloxyarenes to boronic acid pinacol esters via nickel catalysis is described. In contrast to other borylation protocols of inert C-O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Sequential cross-coupling reactions were achieved by leveraging the orthogonal reactivity of silyloxyarenes, which could then be functionalized subsequently.