849061-99-0

Basic information

• Product Name: trans-2-Cyclopropylvinylboronic acid pinacol ester, 96%
• Synonyms: trans-2-Cyclopropylvinylboronic acid pinacol ester, 96%;(E)-2-Cyclopropylethene-1-boronic acid, pinacol ester, trans-2-Cyclopropylvinylboronic acid, pinacol ester;(E)-2-Cyclopropylethylene-1-boronic acid, pinacol ester;(E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;(trans)-2-Cyclopropylvinylboronic acid pinacol ester 96%
• CAS NO: 849061-99-0
• Molecular Formula: C₁₁H₁₉BO₂
• Molecular Weight: 194.08
• Product Categories: Alkenyl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 849061-99-0.mol

Chemical Properties

• Boiling Point: 90-95 °C/3-4 mmHg(lit.)
• Flash Point: 93 °C
• Appearance: /
• Density: 0.937 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.434mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: trans-2-Cyclopropylvinylboronic acid pinacol ester, 96%(CAS DataBase Reference)
• NIST Chemistry Reference: trans-2-Cyclopropylvinylboronic acid pinacol ester, 96%(849061-99-0)
• EPA Substance Registry System: trans-2-Cyclopropylvinylboronic acid pinacol ester, 96%(849061-99-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 849061-99-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Trans-2-Cyclopropylvinylboronic acid pinacol ester, 96% is used as a reagent for facilitating the Suzuki-Miyaura coupling reaction, which is a cross-coupling process for the formation of carbon-carbon bonds. This reaction is crucial in the synthesis of complex organic molecules and plays a significant role in the development of new pharmaceuticals and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trans-2-Cyclopropylvinylboronic acid pinacol ester, 96% is used as a key intermediate in the synthesis of various drug molecules. Its unique structure and reactivity allow for the creation of novel compounds with potential therapeutic applications, contributing to the advancement of drug discovery and development.
Used in Research and Development:
Trans-2-Cyclopropylvinylboronic acid pinacol ester, 96% is employed as a research tool in academic and industrial laboratories. Its high purity and reactivity make it an ideal candidate for exploring new reaction pathways, understanding reaction mechanisms, and optimizing synthetic processes. trans-2-Cyclopropylvinylboronic acid pinacol ester, 96%'s versatility in organic synthesis and its potential applications in drug discovery make it a valuable asset for researchers in the field of chemistry and related disciplines.

InChI:InChI=1/C11H19BO2/c1-10(2)11(3,4)14-12(13-10)8-7-9-5-6-9/h7-9H,5-6H2,1-4H3/b8-7+

Upstream product

• 6746-94-7 Cyclopropylacetylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1034669-87-8 2-[(E)-2-cyclopropylvinyl]-1,3,2-benzodioxaborole 

Downstream Products

• 1441367-71-0 [2-((E)-2-cyclopropylvinyl)-phenyl]phosphonic acid diethyl ester 
• 1441367-94-7 [5-chloro-2-((E)-2-cyclopropylvinyl)phenyl]phosphonic acid diethyl ester 
• 1441368-20-2 [2-((E)-2-cyclopropylvinyl)-5-methoxyphenyl]phosphonic acid diethyl ester 
• 903510-64-5 trans-2-cyclopropylvinylboronic acid 
• 1453804-79-9 C₁₈H₁₇NO 
• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 1401802-42-3 methyl (2E,4E)-5-cyclopropylpenta-2,4-dienoate 

Relevant articles and documents

Hexamethyldisilazane Lithium (LiHMDS)-Promoted Hydroboration of Alkynes and Alkenes with Pinacolborane

Lithium-promoted hydroboration of alkynes and alkenes using commercially available hexamethyldisilazane lithium as a precatalyst and HBpin as a hydride source has been developed. This method will be appealing for organic synthesis because of its remarkable substrate tolerance and good yields. Mechanistic studies revealed that the hydroboration proceeds through the in situ-formed BH3species, which acts to drive the turnover of the hydroboration of alkynes and alkenes.

Creating High Regioselectivity by Electronic Metal-Support Interaction of a Single-Atomic-Site Catalyst

Ligands are the most commonly used means to control the regioselectivity of organic reactions. It is very important to develop new regioselective control methods for organic synthesis. In this study, we designed and synthesized a single-atomic-site catalyst (SAC), namely, Cu1-TiC, with strong electronic metal-support interaction (EMSI) effects by studying various reaction mechanisms. π cloud back-donation to the alkyne on the metal catalytic intermediate was enhanced during the reaction by using transient electron-rich characteristics. In this way, the reaction achieved highly linear-E-type regioselective conversion of electronically unbiased alkynes and completely avoided the formation of branched isomers (ln:br >100:1, TON up to 612, 3 times higher than previously recorded). The structural elements of the SACs were designed following the requirements of the synthesis mechanism. Every element in the catalyst played an important role in the synthesis mechanism. This demonstrated that the EMSI, which is normally thought to be responsible for the improvement in catalytic efficiency and durability in heterogeneous catalysis, now first shows exciting potential for regulating the regioselectivity in homogeneous catalysis.

Electrochemical Hydroboration of Alkynes

Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.

Cs4B4O3F10: First Fluorooxoborate with [BF4] Involving Heteroanionic Units and Extremely Low Melting Point

Herein, a new congruently melting mixed-anion compound Cs4B4O3F10 has been characterized as the first fluorooxoborate with [BF4] involving heteroanionic units. Compound Cs4B4O3F10 possesses two highly fluorinated anionic clusters and therefore its formula can be expressed as Cs3(B3O3F6) ? Cs(BF4). The influence of [BF4] units on micro-symmetry and structural evolution was discussed based on the parent compound. More importantly, Cs4B4O3F10 shows the lowest melting point among all the available borates and thus sets a new record for such system. This work is of great significance to enrich and tailor the structure of borates using perfluorinated [BF4] units.

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3. (Figure presented.).

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.

Aluminum-Catalyzed Selective Hydroboration of Nitriles and Alkynes: A Multifunctional Catalyst

The reaction of LH [L = {(ArNH)(ArN)-C=N-C=(NAr)(NHAr)}; Ar =2,6-Et2-C6H3] with a commercially available alane amine adduct (H3Al·NMe2Et) in toluene resulted in the formation of a conjugated bis-guanidinate (CBG)-supported aluminum dihydride complex, i.e., LAlH2 (1), in good yield. The new complex has been thoroughly characterized by multinuclear magnetic resonance, IR, mass, and elemental analyses, including single-crystal structural studies. Further, we have demonstrated the aluminum-catalyzed hydroboration of a variety of nitriles and alkynes. Moreover, aluminum-catalyzed hydroboration is expanded to more challenging substrates such as alkene, pyridine, imine, carbodiimide, and isocyanides. More importantly, we have shown that the aluminum dihydride catalyzed both intra- A nd intermolecular chemoselective hydroboration of nitriles and alkynes over other reducible functionalities for the first time.

Practical Solvent-Free Microwave-Assisted Hydroboration of Alkynes

A simple and rapid protocol for the anti-Markovnikov hydroboration of alkynes assisted by microwave irradiation has been developed. Pinacolborane smoothly reacts with terminal alkynes to obtain (E)-alkenyl boronates in good yields and short reactions times in the absence of solvent. Further transformations on the carbon-boron bond of the adducts can be sequentially achieved without the need of purifying the alkenyl boronates.

Kinetics and Mechanism of the Arase-Hoshi R2BH-Catalyzed Alkyne Hydroboration: Alkenylboronate Generation via B-H/C-B Metathesis

The mechanism of R2BH-catalyzed hydroboration of alkynes by 1,3,2-dioxaborolanes has been investigated by in situ 19F NMR spectroscopy, kinetic simulation, isotope entrainment, single-turnover labeling (10B/2H), and density functional theory (DFT) calculations. For the Cy2BH-catalyzed hydroboration 4-fluorophenylacetylene by pinacolborane, the resting state is the anti-Markovnikov addition product ArCH = CHBCy2. Irreversible and turnover-rate limiting reaction with pinacolborane (k ≈ 7 × 10-3 M-1 s-1) regenerates Cy2BH and releases E-Ar-CH═CHBpin. Two irreversible events proceed in concert with turnover. The first is a Markovnikov hydroboration leading to regioisomeric Ar-C(Bpin)═CH2. This is unreactive to pinacolborane at ambient temperature, resulting in catalyst inhibition every ～102 turnovers. The second is hydroboration of the alkenylboronate to give ArCH2CH(BCy2)Bpin, again leading to catalyst inhibition. 9-BBN behaves analogously to Cy2BH, but with higher anti-Markovnikov selectivity, a lower barrier to secondary hydroboration, and overall lower efficiency. The key process for turnover is B-H/C-B metathesis, proceeding by stereospecific transfer of the E-alkenyl group within a transient, μ-B-H-B bridged, 2-electron-3-center bonded B-C-B intermediate.

Zinc-Catalysed Hydroboration of Terminal and Internal Alkynes

A regioselective hydroboration of alkynes has been developed by using commercially available zinc triflate as a catalyst, in the presence of catalytic amount of NaBHEt3. The reaction tolerates a wide range of terminal alkynes having several synthetically useful functional groups and proceeds regioselectively to furnish hydroborated products in moderate to excellent yields. This system shows moderate chemoselectivity towards terminal C≡C bond over terminal and internal C=C bond and internal C≡C bond.