69190-62-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a synthetic intermediate for the preparation of fusaric acid and its analogs. These compounds have potential applications as inhibitors of quorum sensing in bacteria, which is an important mechanism for bacterial communication and coordination. By inhibiting quorum sensing, fusaric acid and its analogs can help control bacterial infections and prevent the development of antibiotic resistance.
Additionally, 2-butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used in the synthesis of various pharmaceutical compounds due to its reactivity and stability. Its ability to participate in various types of chemical reactions, such as Suzuki-Miyaura cross-coupling reactions, makes it a valuable building block for the development of new drugs and therapeutic agents.

InChI:InChI=1/C10H21BO2/c1-6-7-8-11-12-9(2,3)10(4,5)13-11/h6-8H2,1-5H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 2117-94-4 butylboronic acid dimethyl ester 
• 4426-47-5 butylboronic acid 
• 590-18-1 (Z)-2-Butene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 109-65-9 1-bromo-butane 
• 73183-34-3 bis(pinacol)diborane 
• 109-69-3 n-Butyl chloride 
• 542-69-8 1-iodo-butane 
• 1191-47-5 dibutylmagnesium 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 200432-99-1 2-(2-bromohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 109-72-8 n-butyllithium 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 18272-84-9 4-n-butylanisole 
• 37920-25-5 1-(4-butylphenyl)ethanone 
• 62702-03-8 1-n-butyl-4-tert-butyl-1-cyclohexene 
• 159656-91-4 -2-methyl-4,5-dicyclohexyl-1,3,2-dioxaborolane 
• 1136153-73-5 N-((2S)-2-hydroxy-2-phenylhex-1-yl)-2-methylpropane-2-sulfonamide 
• 1136153-63-3 N-((1S,2S)-2-hydroxy-1-phenylhex-1-yl)-2-methylpropane-2-sulfonamide 
• 4938-52-7 1-hepten-3-ol 
• 1009-14-9 phenyl butyl ketone 
• 5041-39-4 (E)-hex-1-en-1,2-diyldibenzen 
• 5041-40-7 (Z)-hex-1-en-1,2-diyldibenzen 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 444343-55-9 butyltrifluoro-λ⁴-borane potassium salt 

Relevant academic research and scientific papers

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

A highly efficient photocatalytic protocol for borylation of alkyl bromides and chlorides with graphene supported Cu/Pd alloy nanoparticles as a heterogeneous catalyst is reported. This photocatalytic system operates with visible light in air, providing a wide range of primary and secondary alkyl halides with B2pin2 or B2neop2 in high yields at low temperatures, thereby demonstrating its broad utility and functional group tolerance. The high performance is attributed to a synergistic effect of localized surface plasmon resonance (LSPR) of Cu and charge transfer from Cu to Pd due to the alloy surface charge heterogeneity. Transfer of energetic electrons from Pd to electrophilic alkyl halides lead to the formation of the alkyl radicals, which quickly react with a nucleophilic adduct of a diboron compound with base adsorbed on the positively charged Cu sites to form the corresponding borylation product.

Light-Mediated Sulfur-Boron Exchange

Interaction of sulfides bearing a tetrafluoropyridinyl group with bis(catecholato)diboron followed by treatment with pinacol and triethylamine affording pinacol boronic esters is described. The reaction is promoted by an organic photocatalyst (3DPA2FBN) u

Efficient synthesis of alkylboronic esters: Via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

We report a magnetically separable Cu nanocatalyst (Fe-DOPA-Cu) for the borylation of alkyl halides with alkoxy diboron reagents, providing alkylboronic esters in high yields, with broad functional group tolerance under mild reaction conditions. The procedure is also applicable to the borylation of benzyl chlorides and bromides. Radical clock experiments support a radical-mediated process. Easy recycling of the catalyst resulted in no significant loss of activity up to ten runs.

N-Methylation and Trideuteromethylation of Amines via Magnesium-Catalyzed Reduction of Cyclic and Linear Carbamates

A new reduction of carbamates to N-methyl amines is presented. The magnesium-catalyzed reduction reaction allows the conversion of cyclic and linear carbamates, including N-Boc protected amines, into the corresponding N-methyl amines and amino alcohols which are of significant interest due to their presence in many biologically active molecules. Furthermore, the reduction can be extended to the formation of N-trideuteromethyl labeled amines.

Magnesium-Catalyzed Hydroboration of Terminal and Internal Alkynes

A magnesium-catalyzed hydroboration of alkynes providing good yields and selectivities for a wide range of terminal and symmetrical and unsymmetrical internal alkynes has been developed. The compatibility with many functional groups makes this magnesium c

Chemoselective Luche-Type Reduction of α,β-Unsaturated Ketones by Magnesium Catalysis

The chemoselective reduction of α,β-unsaturated ketones by use of an economic and readily available Mg catalyst has been developed. Excellent yields for a wide range of ketones have been achieved under mild reaction conditions, short times, and low catalyst loadings (0.2-0.5 mol %).

Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron “Ate” Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger

Catalytic enantioselective conjunctive cross-couplings that employ Grignard reagents are shown to furnish an array of nonracemic chiral organoboronic esters in an efficient and highly selective fashion. The utility of sodium triflate in facilitating this reaction is two-fold: it enables “ate” complex formation and overcomes catalytic inhibition by halide ions.

Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki-Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.