1360914-08-4

Basic information

• Product Name: Cyclobutylboronic acid pinacol ester
• Synonyms: Cyclobutylboronic acid pinacol ester;2-cyclobutyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 1360914-08-4
• Molecular Formula: C10H21BO3
• Molecular Weight: 200.08294
• Mol File: 1360914-08-4.mol

Chemical Properties

• Boiling Point: 200.8±9.0 °C(Predicted)
• Appearance: /
• Density: 0.94±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: Cyclobutylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutylboronic acid pinacol ester(1360914-08-4)
• EPA Substance Registry System: Cyclobutylboronic acid pinacol ester(1360914-08-4)

Safety Data

• Hazardous Substances Data: 1360914-08-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Cyclobutylboronic acid pinacol ester is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds. Its unique reactivity and stability make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, Cyclobutylboronic acid pinacol ester is used as a key intermediate in the synthesis of various drugs. Its ability to form carbon-carbon and carbon-heteroatom bonds facilitates the creation of diverse molecular structures with potential therapeutic applications.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, Cyclobutylboronic acid pinacol ester is utilized as a building block for the development of new agrochemicals. Its versatility in forming different types of chemical bonds contributes to the design of innovative and effective products for agricultural use.
Used in Cross-Coupling Reactions:
Cyclobutylboronic acid pinacol ester is employed as a reagent in cross-coupling reactions, a widely used method in organic chemistry for the formation of carbon-carbon bonds. The pinacol ester group enhances the reactivity of the boronic acid, making it a preferred choice for such transformations.
Overall, Cyclobutylboronic acid pinacol ester's unique properties and reactivity make it a valuable asset in various applications across different industries, particularly in the synthesis of complex organic molecules for pharmaceuticals, agrochemicals, and other chemical research areas.

Upstream product

• 4399-47-7 Bromocyclobutane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 849052-26-2 cyclobutyl boronic acid 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1120-57-6 chlorocyclobutane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 

Downstream Products

• 1065010-88-9 potassium cyclobutyltrifluoroboranuide 

Relevant articles and documents

Borylation of primary and secondary alkyl bromides catalyzed by Cu2O nanoparticles

A Cu2O nanoparticle catalyzed borylation of activated and unactivated alkyl bromides is developed, using bis(pinacolato)diboron as a boron source. To the best of our knowledge this is the first report of a heterogeneous Cu2O nanocata

Ring-Opening Lithiation–Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

Stereogenic trifluoromethyl-substituted carbon centers are highly sought-after moieties in pharmaceutical and agrochemical discovery. Here, we show that lithiation–borylation reactions of 2-trifluoromethyl oxirane give densely functionalized and highly versatile trifluoromethyl-substituted α-tertiary boronic esters. The intermediate boronate complexes undergo the desired 1,2-rearrangement of the carbon-based group with complete retentive stereospecificity, a process that was only observed in non-polar solvents in the presence of TESOTf. Although the trifluoromethyl group adversely affects subsequent transformations of the α-boryl group, Zweifel olefinations provide trifluoromethyl-bearing quaternary stereocenters substituted with alkenes, alkynes and ketones.

Electrochemically promoted decarboxylative borylation of alkyl N-hydroxyphthalimide esters

An electrochemically promoted decarboxylative borylation reaction is reported. The reaction proceeds under mild conditions in an undivided cell without use of transition metal- or photo-catalysts. The key feature of the reaction is the compatibility of di

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.).

Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions

Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.

Method for directly preparing alkyl borate compound from alkyl halide

The invention relates to a method for directly preparing an alkyl borate compound from an alkyl halide, which comprises the following steps: in a protective atmosphere, mixing a titanium metal catalyst, an alkali compound, a borate compound and an alkyl halide or sulfonate compound, reacting at 35-100 DEG C for 8-24 hours, so that the alkyl halide or sulfonate compound is directly converted into the alkyl boronic acid pinacol ester compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate application range.

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

An unprecedented and general titanium-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X=I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of titanium catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. A series of synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of our strategy to aryl bromides is also demonstrated.

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.

Decarboxylative Borylation of Stabilized and Activated Carbon Radicals

Redox-active esters (RAEs) as active radical precursors have been extensively studied for C?B bond formations. However, the analogous transformations of stabilized radicals from the corresponding acid precursors remain challenging owing to the strong preference towards single-electron oxidation to the stable carbocations. This work describes a general strategy for rapid access to various aliphatic and aromatic boronic esters by mild photoinduced decarboxylative borylation. Both aryl and alkyl radicals could be generated from the leaving group-assisted N-hydroxybenzimidoyl chloride esters, even α-CF3 substituted substrates could be activated for further elaboration.

Hydrogen Atom Transfer Induced Boron Retaining Coupling of Organoboronic Esters and Organolithium Reagents

α-Functionalization of alkyl boronic esters and homologation of aryl boronic esters by regioselective radical C(sp3)-H activation in boron-ate complexes is reported. Reaction of commercial or readily accessed aryl boronic acid pinacol esters with alkyl lithium reagents provides boron-ate complexes. Selective α-C-H abstraction by in situ generated trifluoromethyl radicals leads to radical anions that undergo electron transfer oxidation followed by 1,2-aryl/alkyl migration from boron to carbon to give the α-arylated/alkylated alkyl boronic esters. The valuable boronic ester functionality remains in the products and the cheap trifluoromethyl iodide acts as the oxidant in these C-C couplings. The 1,2-alkyl migration from boron to carbon is highly stereospecific allowing access to stereoisomerically pure boronic esters.