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

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 73183-34-3 bis(pinacol)diborane 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 403-46-3 4-fluoro-N,N-dimethylaniline 
• 2388-51-4 p-dimethylaminoselenoanisole 

Downstream Products

• 27104-67-2 4-(N,N-dimethylamino)-2'-carbonitrile-1,1'-biphenyl 
• 2143-87-5 N,N-dimethyl-4-(4-nitrophenyl)aniline 
• 1008756-41-9 4-(1-(4-(dimethylamino)phenyl)-2-(thiophen-2-yl)vinyl)-N,N-dimethylbenzenamine 
• 1033592-52-7 p-trimethylammoniophenylboronylpinacolate iodide 
• 1025065-93-3 [4-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-phenyl]-dimethylamine 
• 1130489-34-7 C₂₃H₂₂N₄ 
• 1173167-27-5 Zn(C₂₀H₈N₄(C₆H₄N(CH₃)2)2(C₆H₃(C(CH₃)3)2)2) 
• 366-29-0 N,N,N',N'-tetramethylbenzidine 
• 1187951-66-1 C₂₅H₂₄N₄O₂S 
• 112209-11-7 C₁₄H₈(C₆H₄N(CH₃)2)Br 
• 92194-03-1 4′-bromo-N,N-dimethyl[1,1′-biphenyl]-4-amine 
• 1202-25-1 methyl 4-(N,N-dimethylamino)benzoate 
• 18523-44-9 p-(dimethylamino)phenyl azide 
• 5085-71-2 4-dimethylaminophenylcycloheptane 

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

Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel-Catalyzed Direct Decarbonylative Borylation

The Ni-catalyzed decarbonylative borylation of (hetero)aryl carboxylic acids with B2cat2 has been achieved without recourse to any additives. This Ni-catalyzed method exhibits a broad substrate scope covering poorly reactive non-ortho-substituted (hetero)aryl carboxylic acids, and tolerates diverse functional groups including some of the groups active to Ni0 catalysts. The key to achieve this decarbonylative borylation reaction is the choice of B2cat2 as a coupling partner that not only acts as a borylating reagent, but also chemoselectively activates aryl carboxylic acids towards oxidative addition of their C(acyl)?O bond to Ni0 catalyst via the formation of acyloxyboron compounds. A combination of experimental and computational studies reveals a detailed plausible mechanism for this reaction system, which involves a hitherto unknown concerted decarbonylation and reductive elimination step that generates the aryl boronic ester product. This mode of boron-promoted carboxylic acid activation is also applicable to other types of reactions.