40312-14-9

Usage

Uses

Used in Organic Chemistry:
N-HYDROXY-2-METHYL-BENZAMIDINE is used as a reagent in organic chemistry for the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, facilitating the creation of new molecules and compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, N-HYDROXY-2-METHYL-BENZAMIDINE is utilized as a key intermediate in the development of new drugs. Its potential antimicrobial and antifungal properties make it a promising candidate for the creation of novel therapeutic agents.
Used in Coordination Chemistry:
N-HYDROXY-2-METHYL-BENZAMIDINE also serves as a ligand in coordination chemistry, where it forms complexes with metal ions. This application is crucial for the study of metal-organic interactions and the development of new materials with specific properties.
Used in Antimicrobial and Antifungal Applications:
N-HYDROXY-2-METHYL-BENZAMIDINE has been studied for its potential antimicrobial and antifungal properties, making it a valuable asset in the development of new drugs to combat resistant strains of bacteria and fungi.

InChI:InChI=1/C8H10N2O/c1-6-4-2-3-5-7(6)8(9)10-11/h2-5,11H,1H3,(H2,9,10)

Upstream product

• 529-19-1 2-Methylbenzonitrile 
• 14683-79-5 salicylaldoxime 
• 529-20-4 2-methylphenyl aldehyde 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 132198-47-1 3-(2-Methylphenyl)-1-oxa-2,4-diaza-spiro<4.5>decen-2 
• 124463-95-2 di-o-tolyl-[1,2,4]oxadiazole 
• 94192-15-1 3-<(3-o-Tolyl)-1,2,4-oxadiazol-5-yl>propionic acid 
• 138528-20-8 5,5'-(1,2-ethanediyl)-bis<3-(o-tolyl)-1,2,4-oxadiazole> 
• 1345020-51-0 5-butyl-3-o-tolyl-1,2,4-oxadiazole 
• 1345020-52-1 5-neopentyl-3-o-tolyl-1,2,4-oxadiazole 
• 1345020-53-2 5-(2-iodophenyl)-3-o-tolyl-1,2,4-oxadiazole 
• 26925-60-0 3-(2-methylphenyl)-1,2,4-oxadiazol-5(4H)-one 
• 88303-26-8 C₁₀H₁₂N₂O₂ 
• 137479-24-4 2-phenyl-4-(2-methylphenyl)-2,3-dihydro-1,3,5,2-oxadiazaborol 
• 75907-96-9 5-(3,3-Dinitrobutyl)-3-(2-methylphenyl)-1,2,4-oxadiazole 
• 111457-43-3 3-o-Tolyl-4H-[1,2,4]oxadiazin-5-one 
• 60580-24-7 5-chloromethyl-3-o-tolyl-[1,2,4]oxadiazole 
• 87944-74-9 5-Methyl-3-(o-tolyl)-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Synthesis and Biological Screening of Novel 5-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole Derivatives

A new series of 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole (6a-o) have been synthesized by a cyclocondensation reaction of ethyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate (3a-c) with aryl imidoxime (5a-e). The newly synthesize

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators

Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py

Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles

Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.

Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence

A simple and convenient one-pot method is reported for the synthesis of (E)-3-(3-aryl(heteroaryl, alkyl)-1,2,4-oxadiazole-5-yl)acrylic acids utilizing readily accessible or commercially available substituted benzamidoximes and inexpensive exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. The method is based on the reaction of amidoximes with the anhydride in a basic medium at RT followed by an acid-catalyzed retro-Diels-Alder reaction. The observed stereoselective heterocyclization/retro-Diels-Alder cascade process is suitable for the synthesis of a wide range of substituted (E)-1,2,4-oxadiazole-5-ylacrylic acids featuring electron donating and electron withdrawing groups on the aryl moiety, as well as heteroaryl or alkyl substituents at position 3 of the 1,2,4-oxadiazole ring (42–79%; 15 examples).

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

Efficient Synthesis of Functionalized Indene Derivatives via Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and Allylic Alcohols

A highly efficient rhodium(III)-catalyzed synthesis of novel functionalized indene derivatives has been achieved via C?H activation/intramolecular aldol condensation. This cascade reaction is an atom economical protocol which could be further applied to build more complex compounds. (Figure presented.).

Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure–Activity Relationships, and Sleep-Promoting Properties in Rats

The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzooxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chemical instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats.

A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement

A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.

Rhodium-catalyzed synthesis of 1-(acylamino)isoquinolines through direct annulative coupling of 3-aryl-1,2,4-oxadiazoles with alkynes

A Rh(III)-catalyzed direct annulative coupling of 3-aryl-1,2,4-oxadiazoles with alkynes through coordination-assisted CH activation is developed, providing a facile route to 1-(acylamino)isoquinolines. The oxadiazole ring acts as a directing group as well as an internal oxidant.

Palladium-Catalyzed, Silver-Assisted Direct C-5–H Arylation of 3-Substituted 1,2,4-Oxadiazoles under Microwave Irradiation

A direct C-5–H arylation of 3-substituted 1,2,4-oxadiazoles with aryl iodides in the presence of a palladium catalyst and silver acetate is reported. This method provides a rapid, reliable way to obtain versatile 3,5-diaryl-1,2,4-oxadiazole derivatives, which are common moieties of many biologically active molecules. The synthetic applications of this novel method have been demonstrated in the concise syntheses of Ataluren and a potent RET inhibitor Yhhu251. (Figure presented.).