625458-85-7

Basic information

• Product Name: 4-Butylphenylboronic acid pinacol ester
• Synonyms: 4-Butylphenylboronic acid pinacol ester;2-(4-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 625458-85-7
• Molecular Formula: C₁₆H₂₅BO₂
• Molecular Weight: 260.1795
• Mol File: 625458-85-7.mol

Chemical Properties

• Boiling Point: 345.2±21.0 °C(Predicted)
• Appearance: /
• Density: 0.96±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-Butylphenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Butylphenylboronic acid pinacol ester(625458-85-7)
• EPA Substance Registry System: 4-Butylphenylboronic acid pinacol ester(625458-85-7)

Safety Data

• Hazardous Substances Data: 625458-85-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Butylphenylboronic acid pinacol ester is used as a reagent in Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds to create new organic molecules. This is crucial in the development of new pharmaceuticals with improved efficacy and safety profiles.
Used in Agrochemical Industry:
4-Butylphenylboronic acid pinacol ester is used as a reagent in Suzuki-Miyaura cross-coupling reactions to synthesize agrochemicals with enhanced properties, such as increased effectiveness and reduced environmental impact.
Used in Organic Synthesis:
4-Butylphenylboronic acid pinacol ester is used as a versatile intermediate in the synthesis of various organic compounds, including those with potential applications in materials science, fragrances, and dyes. Its reactivity in cross-coupling reactions allows for the creation of complex molecular structures with diverse functional groups.

Upstream product

• 41492-05-1 p-bromobutylbenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 15499-27-1 4-n-butylchlorobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 73183-34-3 bis(pinacol)diborane 
• 28788-62-7 4-butylbenzoyl chloride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 121-43-7 Trimethyl borate 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 
• 104-51-8 1-butylbenzene 

Downstream Products

• 60040-13-3 4-Amino-4'-butoxybiphenyl 
• 1088098-16-1 2,7-bis(4-n-butyphenyl)-N-methylcarbazole 
• 61342-04-9 1-butyl-4-(trifluoromethyl)benzene 
• 1360760-94-6 1-butyl-4-(perfluoropropyl)benzene 
• 104-51-8 1-butylbenzene 
• 20651-65-4 4-(n-butyl)fluorobenzene 
• 72302-30-8 1-butyl-4-deuteriobenzene 
• 1429377-93-4 2,6-di(4-butylphenyl)dithieno[3,2-b:2′,3′-d]thiophene 
• 1451206-55-5 C₁₄H₁₅NO₂S 
• 334988-37-3 2-(4-n-butylphenyl)pyridine 

Relevant articles and documents

Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents

A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.

Azo bond formation on metal surfaces

The formation of azo compounds via redox cross-coupling of nitroarenes and arylamines, challenging in solution phase chemistry, is achieved by on-surface chemistry. Reaction products are analyzed with a cryogenic scanning tunneling microscope (STM) and X-ray photoelectron spectroscopy (XPS). By using well-designed precursors containing both an amino and a nitro functionality, azo polymers are prepared on surface via highly efficient nitro-amino cross-coupling. Experiments conducted on other substrates and surface orientations reveal that the metal surface has a significant effect on the reaction efficiency. The reaction was further found to proceed from partially oxidized/reduced precursors in dimerization reactions, shedding light on the mechanism that was studied by DFT calculations.

Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes

A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.

Nickel-Catalyzed C(sp2)-H Borylation of Arenes

In this study, C(sp2)-H borylation of arenes was accomplished by a nickel catalyst, resulting in good yield. Alkyl and alkoxy arenes were successfully functionalized, affording C(sp2)-H borylated compounds. It was unraveled that the well-defined abnormal N-heterocyclic carbene based Ni(II) complex breaks into Ni nanoparticles (Ni-NPs), which act as catalytically active species. A series of controlled reactions under stoichiometric conditions along with spectroscopic studies and single-crystal X-ray crystallographic study helped us to understand the formation of Ni-NPs along with formation of a boron(III) compound during this reaction.

Nickel-catalysed decarbonylative borylation of aroyl fluorides

The first Ni(cod)2/PPh3 catalyst system has been established for decarbonylative borylation of aroyl fluorides with bis(pinacolato)diboron. A wide range of functional groups in the substrates were well tolerated. The ease of access of the starting aroyl fluorides indicates that these results might become an alternative to the existing decarbonylation events.

Highly Soluble p-Terphenyl and Fluorene Derivatives as Efficient Dopants in Plastic Scintillators for Sensitive Nuclear Material Detection

Plastic scintillators are commonly used as first-line detectors for special nuclear materials. Current state-of-the-art plastic scintillators based on poly(vinyltoluene) (PVT) matrices containing high loadings (>15.0 wt %) of 2,5-diphenyloxazole (PPO) off

2-Aryl-indenylphosphine ligands: Design, synthesis and application in Pd-catalyzed Suzuki-Miyaura coupling reactions

A focused library of phosphine ligands was constructed for structural optimization. The catalyst can be used to perform the Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl chlorides.

MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS

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2,6-Dialkylphenyldithieno[3,2-b:2',3'-d]thiophene derivatives (DPCn-DTT) were synthesized and characterized. Effect of alkyl groups on optical characteristics, electrochemical properties, film-forming ability, and field-effect performance was studied. The

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A liquid crystal compound with high optical anisotropy is provided. The liquid crystal compound is represented by formula (I), wherein each of R1 and R2 represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;