857530-80-4 Usage
Description
3,5-Dimethylpyrazole-4-boronic acid pinacol ester is a white to beige powder that serves as a versatile intermediate in the synthesis of various organic compounds and pharmaceutical agents. Its unique chemical structure allows it to participate in palladium-catalyzed Suzuki coupling reactions, making it a valuable building block in organic chemistry and drug discovery.
Uses
Used in Pharmaceutical Synthesis:
3,5-Dimethylpyrazole-4-boronic acid pinacol ester is used as a key intermediate for the synthesis of 9H-pyrimido[4,5-b]indole and aryl-benzimidazole based BET bromodomain and extra terminal (BET) protein inhibitors. These inhibitors play a crucial role in the development of novel therapeutic agents targeting various diseases, including cancer and inflammatory disorders.
Used in Photochromic Molecule Synthesis:
In the field of photochemistry, 3,5-dimethylpyrazole-4-boronic acid pinacol ester is used as a reactant to prepare naphthalimide-based photo-exchangeable photochromic fluorescent molecules. These molecules exhibit unique properties, such as reversible color changes upon exposure to light, making them suitable for applications in optical data storage, smart materials, and sensors.
Used in DNA-Encoded Chemical Libraries:
3,5-Dimethylpyrazole-4-boronic acid pinacol ester is employed as a reactant in the development of DNA-encoded chemical libraries through palladium-catalyzed Suzuki coupling reactions with DNA-linked aryl halides. This innovative approach allows for the rapid and efficient exploration of chemical space, facilitating the discovery of new bioactive compounds and accelerating the drug development process.
Check Digit Verification of cas no
The CAS Registry Mumber 857530-80-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,5,7,5,3 and 0 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 857530-80:
(8*8)+(7*5)+(6*7)+(5*5)+(4*3)+(3*0)+(2*8)+(1*0)=194
194 % 10 = 4
So 857530-80-4 is a valid CAS Registry Number.
InChI:InChI=1/C11H19BN2O2/c1-7-9(8(2)14-13-7)12-15-10(3,4)11(5,6)16-12/h1-6H3,(H,13,14)
857530-80-4Relevant articles and documents
Iridium-catalyzed C-H borylation of heteroarenes: Scope, regioselectivity, application to late-stage functionalization, and mechanism
Larsen, Matthew A.,Hartwig, John F.
supporting information, p. 4287 - 4299 (2014/04/03)
A study on the iridium-catalyzed C-H borylation of heteroarenes is reported. Several heteroarenes containing multiple heteroatoms were found to be amenable to C-H borylation catalyzed by the combination of an iridium(I) precursor and tetramethylphenanthroline. The investigations of the scope of the reaction led to the development of powerful rules for predicting the regioselectivity of borylation, foremost of which is that borylation occurs distal to nitrogen atoms. One-pot functionalizations are reported of the heteroaryl boronate esters formed in situ, demonstrating the usefulness of the reported methodology for the synthesis of complex heteroaryl structures. Application of this methodology to the synthesis and late-stage functionalization of biologically active compounds is also demonstrated. Mechanistic studies show that basic heteroarenes can bind to the catalyst and alter the resting state from the olefin-bound complex observed during arene borylation to a species containing a bound heteroarene, leading to catalyst deactivation. Studies on the origins of the observed regioselectivity show that borylation occurs distal to N-H bonds due to rapid N-H borylation, creating an unfavorable steric environment for borylation adjacent to these bonds. Computational studies and mechanistic studies show that the lack of observable borylation of C-H bonds adjacent to basic nitrogen is not the result of coordination to a bulky Lewis acid prior to C-H activation, but the combination of a higher-energy pathway for the borylation of these bonds relative to other C-H bonds and the instability of the products formed from borylation adjacent to basic nitrogen.