459409-74-6

Basic information

• Product Name: 2-PHENYLTHIOPHENE-5-BORONIC ACID PINACOL ESTER
• Synonyms: 2-PHENYLTHIOPHENE-5-BORONIC ACID PINACOL ESTER;5-PHENYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER;4,4,5,5-TetraMethyl-2-(5-phenylthiophen-2-yl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(5-phenylthiophene-2-yl)-1,3,2-dioxaborola;5-Phenyl-2-thienylboronic acid, pinacol ester
• CAS NO: 459409-74-6
• Molecular Formula: C₁₆H₁₉BO₂S
• Molecular Weight: 286.2
• Mol File: 459409-74-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 409.3±33.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 2-PHENYLTHIOPHENE-5-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLTHIOPHENE-5-BORONIC ACID PINACOL ESTER(459409-74-6)
• EPA Substance Registry System: 2-PHENYLTHIOPHENE-5-BORONIC ACID PINACOL ESTER(459409-74-6)

Safety Data

• Hazardous Substances Data: 459409-74-6(Hazardous Substances Data)

Usage

General Description

2-Phenylthiophene-5-boronic acid pinacol ester is a chemical compound that belongs to the family of boronic acids, which are widely used in organic synthesis and pharmaceutical research. This particular compound is derived from thiophene, a heterocyclic compound widely studied for its various potential applications in materials science and medicinal chemistry. The pinacol ester group enhances the stability and reactivity of the boronic acid, making it a versatile building block for the synthesis of complex organic molecules. 2-Phenylthiophene-5-boronic acid pinacol ester may be used as a reactant in chemical reactions to form new carbon-carbon and carbon-heteroatom bonds, making it a valuable tool in the development of new drugs, agrochemicals, and materials.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 306934-95-2 2-phenylthiophen-5-ylboronic acid 
• 29488-24-2 2-Bromo-5-phenyl-thiophene 
• 825-55-8 2-phenylthiophene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 108-86-1 bromobenzene 
• 1408285-51-7 4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane 
• 591-50-4 iodobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1408285-70-0 5-(5-(4-nitrophenyl)thiophen-2-yl)furan-2-carbaldehyde 
• 5069-26-1 2-methyl-5-phenylthiophene 
• 1445-78-9 2,5-Diphenyl-thiophene 
• 825-55-8 2-phenylthiophene 

Relevant articles and documents

Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives

Aryl boronic esters are bench-stable, platform building-blocks that can be accessed through metal-catalyzed aryl C(sp2)-H borylation reactions. C(sp2)-H bond functionalization reactions using rare- and precious-metal catalysts are well established, and while examples utilizing Earth-abundant alternatives have emerged, manganese catalysis remains lacking. The manganese-catalyzed C-H borylation of furan and thiophene derivatives is reported alongside an in situ activation method providing facile access to the active manganese hydride species. Mechanistic investigations showed that blue light irradiation directly affected catalysis by action at the metal center, that C(sp2)-H bond borylation occurs through a C-H metallation pathway, and that the reversible coordination of pinacolborane to the catalyst gave a manganese borohydride complex, which was as an off-cycle resting state.

Dual selectivity: Electrophile and nucleophile selective cross-coupling reactions on a single aromatic substrate

The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.

C-H bond activation/borylation of furans and thiophenes catalyzed by a half-sandwich iron N-heterocyclic carbene complex

A coordinatively unsaturated iron-methyl complex having an N-heterocyclic carbene ligand, [Cp*Fe-(LMe)Me] (1; Cp *=η5-C5Me5, L Me=1,3,4,5-tetramethyl-imidazol-2-ylidene), is synthesized from the reaction of [Cp*Fe(TMEDA)Cl] (TMEDA=N,N,N',N'- tetramethylethylenediamine) with methyllithium and LMe. Complex 1 is found to activate the C-H bonds of furan, thiophene, and benzene, giving rise to aryl complexes, [Cp*Fe(LMe)-(aryl)] (aryl=2-furyl (2), 2-thienyl (3), phenyl (4)). The C-H bond cleavage reactions are applied to the dehydrogenative coupling of furans or thiophenes with pinacolborane (HBpin) in the presence of tert-butylethylene and a catalytic amount of 1 (10 mol% to HBpin). The borylation of the furan/thiophene or 2-substituted furans/thiophenes occurs exclusively at the 2-or 5-positions, respectively, whereas that of 3-substituted furans/thiophenes takes place mainly at the 5-position and gives a mixture of regioisomers. Treatment of 2 with 2 equiv of HBpin results in the quantitative formation of 2-boryl-furan and the borohydride complex [Cp *Fe(LMe)(H2Bpin)] (5). Heating a solution of 5 in the presence of tert-butylethylene led to the formation of an alkyl complex [Cp*Fe-(LMe)CH2CH2tBu] (6), which was found to cleave the C-H bond of furan to produce 2. On the basis of these results, a possible catalytic cycle is proposed.