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Usage

Uses

Used in Pharmaceutical Industry:
TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those containing substituted 1,3-diene structures. Its ability to participate in palladium-catalyzed cross-coupling reactions with olefins allows for the efficient construction of complex molecular frameworks, which are often found in bioactive molecules.
Used in Agrochemical Industry:
In the agrochemical industry, TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER is utilized as a building block for the synthesis of various agrochemicals, such as pesticides and herbicides. The substituted 1,3-dienes generated through its cross-coupling reactions with olefins can be incorporated into the molecular structures of these agrochemicals, potentially enhancing their efficacy and selectivity.
Used in Material Science:
TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER is employed as a precursor in the development of novel materials with unique properties. The substituted 1,3-dienes formed through its cross-coupling reactions can be used to create polymers, coatings, and other materials with tailored characteristics, such as improved stability, reactivity, or conductivity.
Used in Research and Development:
As a versatile reagent in organic synthesis, TRANS-1-HEPTENYLBORONIC ACID PINACOL ESTER is widely used in research and development laboratories. Its ability to participate in palladium-catalyzed cross-coupling reactions with olefins makes it an invaluable tool for the synthesis of new compounds and the exploration of novel reaction pathways.

InChI:InChI=1/C13H25BO2/c1-6-7-8-9-10-11-14-15-12(2,3)13(4,5)16-14/h10-11H,6-9H2,1-5H3/b11-10+

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 628-71-7 1-Heptyne 
• 57404-76-9 trans-1-heptenylboronic acid 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 66-25-1 hexanal 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 

Downstream Products

• 58761-29-8 (E)-undec-5-en-2-one 
• 1356468-03-5 (E)-3-(boronic acid pinacolate ester)-1-phenyl-1-nonene 
• 749885-73-2 Acetic acid (1R,2R)-2-pentyl-cyclopropyl ester 

Relevant academic research and scientific papers

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions

The hydroboration of alkynes is crucial due to the wide applications in organic synthesis, while such reaction is often completed with low turnover frequency (TOF) value and long reaction time. Therefore, it is very important and necessary that the hydrob

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.

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.

Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Boronic esters are versatile building blocks extensively used in organic chemistry and essential to a variety of coupling reactions. In this work, the hydroboration reactions of alkynes were performed without metal catalysts using concomitant microwave ir

Catalyst-free and solvent-free hydroboration of alkynes

The hydroboration of alkynes with pinacolborane (HBpin) under catalyst- and solvent-free conditions was demonstrated. Various alkynes were smoothly converted into alkenyl boronate esters in good to excellent yields at 110 °C. The gram-scale hydroboration

Nickel-Catalyzed Highly Selective Hydroalkenylation of Alkenyl Boronic Esters to Access Allyl Boron

Allyl boron derivatives are valuable building blocks in the synthesis of natural products and bioactive molecules. Herein, a practical strategy of nickel-catalyzed highly selective hydroalkenylation of alkenyl boronic esters was developed. Under the mild

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

Lithium diisobutyl-: Tert-butoxyaluminum hydride (LDBBA) catalyzed hydroboration of alkynes and imines with pinacolborane

Lithium diisobutyl-tert-butoxyaluminum hydride (LDBBA)-catalyzed hydroboration of alkynes with pinacolborane (HBpin) was demonstrated. The hydroboration proceeded more efficiently with LDBBA than with other aluminum hydrides and afforded alkenyl boronates in moderate to good yields. In addition, high-yielding LDBBA-catalyzed hydroboration of imines was achieved. The coordination of anionic aluminate with lithium enables effective hydride transfer for hydroboration.