• 1. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466
• 2. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 3. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 4. Exciton manipulation in rippled transition metal dichalcogenides?
  Chen Long,Ying Dai,Jianwei Li,Hao Jin Nanoscale, 2020,12, 21124-21130
• 5. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625

Introduction to 4-tert-Butylbenzamidoxime (CAS No. 175204-39-4)

4-tert-Butylbenzamidoxime (CAS No. 175204-39-4) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique chemical structure, has shown promise in various applications, particularly in the development of novel therapeutic agents and as a key intermediate in synthetic pathways. This article aims to provide a comprehensive overview of 4-tert-Butylbenzamidoxime, including its chemical properties, synthesis methods, biological activities, and potential applications.

Chemical Properties

4-tert-Butylbenzamidoxime is an amidoxime derivative with the molecular formula C₁₁H₁₅N₃O. It has a molecular weight of 205.25 g/mol and exists as a white crystalline solid at room temperature. The compound is soluble in common organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO), but it has limited solubility in water. The presence of the tert-butyl group imparts additional stability to the molecule, making it suitable for various chemical reactions and biological studies.

The chemical structure of 4-tert-Butylbenzamidoxime consists of a benzene ring substituted with a tert-butyl group at the para position and an amidoxime functional group (-N=NOH) attached to the benzene ring through a carbonyl group. This unique arrangement of functional groups contributes to its reactivity and biological activity.

Synthesis Methods

The synthesis of 4-tert-Butylbenzamidoxime can be achieved through several well-established methods. One common approach involves the reaction of 4-tert-butylbenzamide with hydroxylamine in the presence of an acid catalyst. The reaction typically proceeds via nucleophilic addition of hydroxylamine to the carbonyl group, followed by tautomerization to form the amidoxime product.

A typical synthetic route is as follows:

1. Dissolve 4-tert-butylbenzamide in an appropriate solvent such as ethanol or methanol.
2. Add hydroxylamine hydrochloride and an acid catalyst like hydrochloric acid or acetic acid.
3. Heat the reaction mixture under reflux for several hours until completion.
4. Cool the mixture and filter the precipitated product.
5. Purify the crude product using recrystallization or column chromatography to obtain pure 4-tert-Butylbenzamidoxime.

This method is widely used due to its simplicity and high yield. However, alternative synthetic routes have also been explored to improve efficiency and reduce by-products.

Biological Activities

4-tert-Butylbenzamidoxime has been studied for its potential biological activities, particularly in the context of medicinal chemistry and drug discovery. Recent research has highlighted its role as a potent inhibitor of various enzymes and receptors, making it a valuable lead compound for developing new therapeutic agents.

One notable application is its use as an inhibitor of monoamine oxidase (MAO), an enzyme involved in the breakdown of neurotransmitters such as serotonin, dopamine, and norepinephrine. Inhibition of MAO can have significant implications for treating neurological disorders such as depression and Parkinson's disease. Studies have shown that 4-tert-Butylbenzamidoxime exhibits selective inhibition of MAO-B over MAO-A, which is advantageous for minimizing side effects associated with non-selective inhibitors.

In addition to its enzymatic inhibition properties, 4-tert-Butylbenzamidoxime has also been investigated for its antioxidant activity. Free radicals are known to contribute to cellular damage and are implicated in various diseases such as cancer and cardiovascular disorders. Research has demonstrated that 4-tert-Butylbenzamidoxime can effectively scavenge free radicals, thereby protecting cells from oxidative stress.

Potential Applications

The unique properties of 4-tert-Butylbenzamidoxime make it a promising candidate for various applications in pharmaceutical research and development. Its ability to inhibit MAO-B suggests potential use in treating neurological disorders where increased levels of monoamines are beneficial. Clinical trials are currently underway to evaluate its efficacy and safety profile in this context.

Beyond its direct therapeutic applications, 4-tert-Butylbenzamidoxime can serve as a valuable intermediate in the synthesis of more complex molecules with diverse biological activities. For example, it can be used as a building block for constructing peptidomimetics or other bioactive compounds that target specific receptors or enzymes.

In conclusion, 4-tert-Butylbenzamidoxime (CAS No. 175204-39-4) is a multifaceted compound with significant potential in both fundamental research and practical applications. Its unique chemical structure and biological activities make it an attractive target for further investigation and development in the fields of medicinal chemistry and pharmaceutical science.

• 613-92-3(Benzamide Oxime)
• 328552-93-8(4-(aminomethyl)-N-hydroxybenzene-1-carboximidamide)
• 185148-54-3(Benzenecarboximidamide,2-ethyl-N-hydroxy-)
• 277319-62-7(4-Aminobenzamide Oxime)
• 15325-51-6(1,3-Benzenedicarboximidamide,N1,N3-dihydroxy-)
• 125772-42-1(4-tert-butylbenzene-1-carboximidamide)
• 19227-13-5(N'-Hydroxy-4-methylbenzenecarboximidamide)
• 40067-82-1(N'-Hydroxy-3-methylbenzenecarboximidamide)
• 64893-54-5(N'-Hydroxy-2-naphthalenecarboximidamide)
• 6051-62-3(N1,N4-Dihydroxyterephthalimidamide)