24067-17-2 Usage
Description
4-Nitrophenylboronic acid is an arylboronic acid building block, which is a white to brown powder or crystal. It is a versatile synthetic intermediate and reagent used in various chemical reactions and processes.
Uses
Used in Pharmaceutical Industry:
4-Nitrophenylboronic acid is used as a synthetic intermediate for the preparation of combretastatin analogs, which are potential antitumor agents. It is also used in the synthesis of human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses.
Used in Chemical Synthesis:
4-Nitrophenylboronic acid is used as a reagent for ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, which are essential in the formation of carbon-carbon bonds in organic synthesis. It is also used in ruthenium-catalyzed direct arylation of benzylic sp3 carbons of acyclic amines, Diels-Alder or C-H activation reactions, and regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations.
Used in Environmentally Benign Synthesis:
4-Nitrophenylboronic acid is used in an environmentally benign one-pot synthesis through a double arylation process, which reduces waste and improves efficiency in chemical synthesis.
Used in Copper-Mediated Reactions:
It is used as a reagent in copper-mediated cyanations and copper-catalyzed arylations, which are important for the synthesis of various organic compounds.
Used in Regioselective Glycosylations:
4-Nitrophenylboronic acid is used in regioselective glycosylations, which are crucial for the synthesis of complex carbohydrates and their derivatives.
Used in Suzuki Couplings:
It is used in Suzuki couplings followed by arylations, which are essential for the formation of biaryl compounds and have applications in the synthesis of pharmaceuticals, agrochemicals, and materials.
Used in X-ray Absorption:
4-Nitrophenylboronic acid is used as a reagent on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron-deficient olefins, which is important for the development of new catalytic systems and synthetic methods.
Used in Suzuki Reaction:
4-Nitrophenylboronic acid is used in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds in organic synthesis, particularly useful for the synthesis of complex molecules and biologically active compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 24067-17-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,0,6 and 7 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 24067-17:
(7*2)+(6*4)+(5*0)+(4*6)+(3*7)+(2*1)+(1*7)=92
92 % 10 = 2
So 24067-17-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H6BNO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,9-10H
24067-17-2Relevant articles and documents
Microwave-assisted transition-metal-catalyzed synthesis of N-shifted and ring-expanded buflavine analogues
Appukkuttan, Prasad,Dehaen, Wim,Van Der Eycken, Erik
, p. 6452 - 6460 (2007)
Two novel and efficient strategies for the synthesis of hitherto unknown N-shifted and ring-expanded buflavine analogues are presented. Construction of the medium-sized ring system of the title molecules, a difficult task due to the high activation energy needed for the ring-closure with the additional rigidity imposed by the biaryl skeleton, was achieved by using Suzuki-Miyaura biaryl coupling and a ring-closing metathesis reaction as the key steps. The combination of a second-generation Grubbs catalyst and microwave irradiation proved to be highly useful in generating the otherwise difficult to obtain medium-sized ring system of the buflavine analogues.
Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts
Filimonov, Victor D.,Krasnokutskaya, Elena A.,Kassanova, Assia Zh.,Fedorova, Valentina A.,Stankevich, Ksenia S.,Naumov, Nikolay G.,Bondarev, Alexander A.,Kataeva, Veronika A.
supporting information, p. 665 - 674 (2018/09/14)
Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.
Borinic Acids via Direct Arylation of Amine-Borane Complexes: An Air- and Water-Stable Boron Source
Richard, Jimmy,Birepinte, Mélodie,Charbonnier, Jean Baptiste,Liautard, Virginie,Pinet, Sandra,Pucheault, Mathieu
, p. 736 - 744 (2017/02/15)
A synthesis of borinic acids and borinates was optimized using amine-borane complexes as a water and air insensitive borylating agent. The reaction operates under convenient conditions using a non-cryogenic temperature and with no flash chromatography, and it gives no boron impurities. The reaction proceeds through a tandem dehydrogenation-double addition mechanism.
