949115-04-2

Basic information

• Product Name: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrrole
• CAS NO: 949115-04-2
• Molecular Weight: 269.151
• Mol File: 949115-04-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrrole(949115-04-2)
• EPA Substance Registry System: 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrrole(949115-04-2)

Safety Data

• Hazardous Substances Data: 949115-04-2(Hazardous Substances Data)

Usage

Chemical class

Pyrrole derivative
This compound belongs to the class of pyrrole derivatives, which are heterocyclic compounds containing a nitrogen atom in the ring.

Structure

Contains a boron atom
The presence of a boron atom in its structure gives this compound unique properties and potential applications in various fields.

Functional groups

4,4,5,5-tetramethyl-1,3,2-dioxaborolane moiety
This moiety is a boron-containing group that can be used for further functionalization and cross-coupling reactions.

Potential applications

Organic synthesis, medicinal chemistry, and materials science
Due to its interesting structure and boron-containing moiety, this compound may have uses in these fields.

Reactivity

Subject to further study and research
The precise uses and applications of this chemical may vary depending on its specific properties and reactivity, making it an interesting subject for further study and research.

Stability

Unknown
The stability of this compound under various conditions is not provided in the material and would require further investigation.

Solubility

Unknown
The solubility of this compound in different solvents is not mentioned in the material and would need to be determined experimentally.

Physical state

Unknown
The physical state (solid, liquid, or gas) of this compound at room temperature is not provided in the material and would need to be determined.

Molecular weight

Unknown
The molecular weight of this compound can be calculated from its molecular formula but is not provided in the material.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 92636-36-7 1-(4-iodophenyl)pyrrole 
• 81329-31-9 1-(4-fluorophenyl)-1H-pyrrole 
• 73183-34-3 bis(pinacol)diborane 
• 5044-38-2 1-(4-chlorophenyl)-1H-pyrrole 
• 352-34-1 4-fluoro-1-iodobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 5044-39-3 1-(4-bromophenyl)-1H-pyrrole 

Relevant articles and documents

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Copper-catalysed borylation of aryl chlorides

We report herein the first Cu-catalysed borylation of a wide range of aryl chlorides with different electronic and steric properties using a readily prepared NHC-stabilised Cu catalyst and KOtBu as the base with B2pin2 (pin = pinacolato) as the boron reagent. The aryl chlorides are converted into their corresponding arylboronic esters in good yields. The new procedure shows broad functional group tolerance, and B2neop2 (neop = neopentyl glycolato) can also be applied as the boron reagent.

Efficient Synthesis of Aryl Boronates via Cobalt-Catalyzed Borylation of Aryl Chlorides and Bromides

An efficient catalytic system based on a Co(II)-NHC precursor has been developed for the cross coupling of bis(pinacolato)diboron with aryl halides including aryl chlorides, affording the aryl boronates in good to excellent yields. A wide range of functional groups are tolerated under mild reaction conditions. The reaction shows excellent chemoselectivity for bromide over chloride. Preliminary mechanistic investigations show that the catalytic cycle may rely on a cobalt(I)-(III) redox couple.