87100-15-0

Basic information

• Product Name: Cyclohexylboronic acid pinacol ester
• Synonyms: CYCLOHEXYLBORONIC ACID ACID PINACOL ESTER;2-Cyclohexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;REF DUPL: Cyclohexylboronic acid pinacol ester;Cyclohexylboronic acid pinacol este;(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane;1,3,2-Dioxaborolane, 2-cyclohexyl-4,4,5,5-tetraMethyl-;Cyclohexane acid pinacol ester;CYCLOHEXYLBORONIC ACID PINACOL ESTER
• CAS NO: 87100-15-0
• Molecular Formula: C₁₂H₂₃BO₂
• Molecular Weight: 210.12
• Product Categories: Alkyl;Organoborons
• Mol File: 87100-15-0.mol

Chemical Properties

• Boiling Point: 244.7 °C at 760 mmHg
• Flash Point: 101.8 °C
• Appearance: Colorless/Liquid
• Density: 0.93 g/cm³
• Vapor Pressure: 0.0469mmHg at 25°C
• Refractive Index: 1.4460 to 1.4500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Cyclohexylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexylboronic acid pinacol ester(87100-15-0)
• EPA Substance Registry System: Cyclohexylboronic acid pinacol ester(87100-15-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 87100-15-0(Hazardous Substances Data)

Usage

Uses

Cyclohexylboronic acid, pinacol ester

InChI:InChI=1/C12H23BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h10H,5-9H2,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 110-83-8 cyclohexene 
• 1350934-26-7 5-cyclohexyl-5,6-dihydrobenzo[e]pyrazolo[1,5-c][1,3,2]diazaborinine 
• 766-77-8 Dimethylphenylsilane 
• 542-18-7 cyclohexyl chloride 
• 626-62-0 Cyclohexyl iodide 
• 108-93-0 cyclohexanol 
• 74-84-0 ethane 
• 110-82-7 cyclohexane 
• 73183-34-3 bis(pinacol)diborane 
• 34557-54-5 methane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 32999-09-0 2-cyclohexylbenzo-[d][1,3,2]dioxaborole 
• 1088-01-3 tricyclohexylborane 

Downstream Products

• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 4352-44-7 1-cyclohexylprop-2-en-1-ol 
• 120850-91-1 (S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol 
• 613-36-5 4-cyclohexylanisole 
• 4441-56-9 cyclohexylboronic acid 

Relevant articles and documents

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.).

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.

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.

Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C?Br bond in the brominated product could be readily transformed to a series of C?C, C?O, C?N, C?S, C?P, and C?I bonds, some of which are difficult to forge with α-halo sp2-B boronate esters. An activation effect of B(MIDA) moiety was found.

Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX3/iPr2NEt**

An unprecedented and general hydroboration of alkenes with BX3 (X=Br, Cl) as the boration reagent in the presence of iPr2NEt is reported. The addition of iPr2NEt not only suppresses alkene polymerizat

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

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is

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

Chromium-Catalyzed Borylative Coupling of Aliphatic Bromides with Pinacolborane by Hydrogen Evolution

The chromium-catalyzed borylative coupling between aliphatic bromides and pinacolborane (HBpin) is described. This reaction was promoted by low-cost and bench-stable CrCl3as a precatalyst combined with 4,4′-di-tert-butyl-2,2′-dipyridyl and aluminum, presenting a rare example of using HBpin as a borane reagent by coupling with alkyl bromides in forming borylated alkanes. Mechanistic studies indicate that aluminum plays important roles in the formation of reactive Cr species and aliphatic radicals, which lead to (alkyl)Cr by reaction with HBpin to give the products.

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.