5720-05-8 Usage
Description
4-Tolylboronic acid, also known as 4-Methylbenzeneboronic acid, is a white to light yellow crystal powder with chemical properties that make it a versatile compound in various industries. It is commonly used in Suzuki coupling reactions and serves as an intermediate in the pharmaceutical industry.
Uses
Used in Chemical Synthesis:
4-Tolylboronic acid is used as a reagent for various chemical reactions, including Suzuki coupling, which is a widely employed method for the formation of carbon-carbon bonds. This reaction is particularly useful in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Tolylboronic acid is used as an intermediate for the synthesis of various drugs. Its ability to form carbon-carbon bonds through Suzuki coupling reactions makes it a valuable component in the development of new medications.
Used in Catalyst Preparation:
4-Tolylboronic acid is also used in the preparation of catalysts for Suzuki-Miyaura cross-coupling of aryl bromides. These catalysts are essential for facilitating the reaction and improving the efficiency of the process.
Used in Environmentally Friendly Reactions:
4-Tolylboronic acid is utilized in the development of recyclable palladium nanoparticle catalysts immobilized by click ionic copolymers for Suzuki-Miyaura cross-coupling reactions in water. This application highlights its potential in promoting green chemistry and sustainable practices in the chemical industry.
Used in Direct Arylation:
4-Tolylboronic acid is employed as a reagent in direct arylation reactions, such as Palladium (Pd)-catalyzed direct arylation, Direct Palladium(II)-Catalyzed Synthesis, and Ruthenium-catalyzed direct arylation. These reactions are crucial for the synthesis of various organic compounds and materials.
Used in Tandem Reactions:
4-Tolylboronic acid is also used in tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence, as well as Rhodium-catalyzed asymmetric conjugate addition. These tandem reactions allow for the efficient synthesis of complex molecules in a single operation.
Used in Ligand-Free Cross-Coupling Reactions:
4-Tolylboronic acid is utilized in ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions. These reactions are significant for their simplicity and the ability to form carbon-carbon and carbon-heteroatom bonds without the need for additional ligands.
Used in Regioselective Arylation and Alkynylation:
4-Tolylboronic acid is employed in regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions. These reactions are essential for the precise synthesis of molecules with specific structural features, which is crucial in the development of new drugs and materials.
Check Digit Verification of cas no
The CAS Registry Mumber 5720-05-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,2 and 0 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 5720-05:
(6*5)+(5*7)+(4*2)+(3*0)+(2*0)+(1*5)=78
78 % 10 = 8
So 5720-05-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H13N/c1-8(10-2)9-6-4-3-5-7-9/h3-8,10H,1-2H3/t8-/m1/s1
5720-05-8Relevant articles and documents
Atropisomerism of the C-1-C′-1 axis of 2,2′,8,8′-unsubstituted 1,1′-binaphthyl derivatives
Chow,Wan
, p. 5042 - 5047 (2001)
The Suzuki coupling of optically active (S)-binaphthyl bromide 10 with (S)-binaphthyl boronic acid 11 produced a diastereomeric mixture of tetrahydroxyquaternaphthyls 4. The coupling products 4 as well as their derivatives 5-7 can be considered as members of the family of 1,1′-binaphthyl-3,3′-diols. The C-1-C′-1 axis of all these compounds was found to have an unusually high rotational barrier. Generally, the barrier is higher for derivatives having more bulky substituents at the 3 and 3′ positions.
Bipyridinium and Phenanthrolinium Dications for Metal-Free Hydrodefluorination: Distinctive Carbon-Based Reactivity
Burton, Katherine I.,Elser, Iris,Waked, Alexander E.,Wagener, Tobias,Andrews, Ryan J.,Glorius, Frank,Stephan, Douglas W.
supporting information, p. 11730 - 11737 (2021/07/16)
The development of novel Lewis acids derived from bipyridinium and phenanthrolinium dications is reported. Calculations of Hydride Ion Affinity (HIA) values indicate high carbon-based Lewis acidity at the ortho and para positions. This arises in part from extensive LUMO delocalization across the aromatic backbones. Species [C10H6R2N2CH2CH2]2+ (R=H [1 a]2+, Me [1 f]2+, tBu [1 g]2+), and [C12H4R4N2CH2CH2]2+ (R=H [2 a]2+, Me [2 b]2+) were prepared and evaluated for use in the initiation of hydrodefluorination (HDF) catalysis. Compound [2 a]2+ proved highly effective towards generating catalytically active silylium cations via Lewis acid-mediated hydride abstraction from silane. This enabled the HDF of a range of aryl- and alkyl- substituted sp3(C?F) bonds under mild conditions. The protocol was also adapted to effect the deuterodefluorination of cis-2,4,6-(CF3)3C6H9. The dications are shown to act as hydride acceptors with the isolation of neutral species C16H14N2 (3 a) and C16H10Me4N2 (3 b) and monocationic species [C14H13N2]+ ([4 a]+) and [C18H21N2]+ ([4 b]+). Experimental and computational data provide further support that the dications are initiators in the generation of silylium cations.
Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup
, p. 10966 - 10972 (2020/09/23)
In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.