40067-82-1

Basic information

• Product Name: N'-HYDROXY-3-METHYLBENZENECARBOXIMIDAMIDE
• Synonyms: BUTTPARK 33\11-53;N'-HYDROXY-3-METHYLBENZENECARBOXIMIDAMIDE;Benzenecarboximidamide, N-hydroxy-3-methyl- (9CI);N'-Hydroxy-3-methylbenzenecarboximideamide;N'-Hydroxy-3-methylbenzenecarboximidamide, N'-Hydroxy-3-methylbenzamidine;(E)-3-Hydroxy-2-(quinolin-2-yl)acrylaldehyde;N-hydroxy-3-methylbenzimidamide
• CAS NO: 40067-82-1
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.18
• Product Categories: OXIME;AMIDINE;Nitrogen Compounds;Organic Building Blocks;Oximes
• Mol File: 40067-82-1.mol

Chemical Properties

• Melting Point: 82-87 °C(lit.)
• Boiling Point: 329.5 °C at 760 mmHg
• Flash Point: 153.1 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 7.13E-05mmHg at 25°C
• Refractive Index: 1.564
• PKA: 7.04±0.69(Predicted)
• CAS DataBase Reference: N'-HYDROXY-3-METHYLBENZENECARBOXIMIDAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N'-HYDROXY-3-METHYLBENZENECARBOXIMIDAMIDE(40067-82-1)
• EPA Substance Registry System: N'-HYDROXY-3-METHYLBENZENECARBOXIMIDAMIDE(40067-82-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 40067-82-1(Hazardous Substances Data)

Usage

Uses

N''-Hydroxy-3-methylbenzenecarboximidamide

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

Upstream product

• 620-22-4 3-Methylbenzonitrile 
• 2362-63-2 3-methylthiobenzamide 
• 620-23-5 m-tolyl aldehyde 
• 52707-50-3 3-methylbenzaldehyde oxime 

Downstream Products

• 85322-15-2 [3-m-Tolyl-4H-[1,2,4]oxadiazin-(5Z)-ylidene]-acetic acid ethyl ester 
• 85322-27-6 [3-m-Tolyl-4H-[1,2,4]oxadiazin-(5E)-ylidene]-acetic acid ethyl ester 
• 75907-87-8 O-(4,4-Dinitropentanoyl)-3-methylbenzamidoxime 
• 132198-48-2 3-m-Tolyl-1-oxa-2,4-diaza-spiro[4.5]dec-2-ene 
• 111249-50-4 3-(3-methylphenyl)-5-phenyl-1,2,4-oxadiazole 
• 111249-46-8 5-Phenyl-3-(m-tolyl)-4,5-dihydro-1,2,4-oxadiazole 
• 111249-44-6 5-Methyl-3-(m-tolyl)-4,5-dihydro-1,2,4-oxadiazole 
• 94192-16-2 3-<(3-m-Tolyl)-1,2,4-oxadiazol-5-yl>propionic acid 
• 87944-75-0 5-Methyl-3-(m-tolyl)-1,2,4-oxadiazole 
• 75907-97-0 5-(3,3-Dinitrobutyl)-3-(3-methylphenyl)-1,2,4-oxadiazole 
• 138528-21-9 5,5'-(1,2-ethanediyl)-bis<3-(m-tolyl)-1,2,4-oxadiazole> 
• 94538-44-0 3-(3-toluyl)-5-(3-toluyl)-1,2,4-oxadiazole 
• 1238287-64-3 C₁₈H₂₃N₃O₃ 
• 1352079-36-7 tert-butyl 4-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate 

Relevant articles and documents

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

Discovery of the First Orally Available, Selective KNa1.1 Inhibitor: In Vitro and in Vivo Activity of an Oxadiazole Series

The gene KCNT1 encodes the sodium-activated potassium channel KNa1.1 (Slack, Slo2.2). Variants in the KCNT1 gene induce a gain-of-function (GoF) phenotype in ionic currents and cause a spectrum of intractable neurological disorders in infants and children, including epilepsy of infancy with migrating focal seizures (EIMFS) and autosomal dominant nocturnal frontal lobe epilepsy (ADNFLE). Effective treatment options for KCNT1-related disease are absent, and novel therapies are urgently required. We describe the development of a novel class of oxadiazole KNa1.1 inhibitors, leading to the discovery of compound 31 that reduced seizures and interictal spikes in a mouse model of KCNT1 GoF.

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

Catalyst-free, one-pot strategy to access 3-substituted-5-amino-1,2,4-thiadiazoles in water

A protocol has been devised for the synthesis of 3-substituted 5-amino-1,2,4-thiadiazoles utilizing isothiocyanates, amidoximes and water as an eco-friendly solvent. The strategy involves consecutive C?N and S?N bonds formation in a one-pot reaction under

Fragment based drug design and diversity-oriented synthesis of carboxylic acid isosteres

The medicinal chemist toolbox is plenty of (bio)isosteres when looking for a carboxylic acid replacement. However, systematic assessment of acid surrogates is often time consuming and expensive, while prediction of both physicochemical properties (logP and logD) as well as acidity would be desirable at early discovery stages for a better analog design. Herein in this work, to enable decision making on a project, we have synthesized by employing a Diversity-Oriented Synthetic (DOS) methodology, a small library of molecular fragments endowed with acidic properties. By combining in-silico and experimental methodologies these compounds were chemically characterized and, particularly, with the aim to know their physicochemical properties, the aqueous ionization constants (pKa), partition coefficients logD and logP of each fragment was firstly estimated by using molecular modeling studies and then validated by experimental determinations. A face to face comparison between data and the corresponding carboxylic acid might help medicinal chemists in finding the best replacement to be used. Finally, in the framework of Fragment Based Drug Design (FBDD) the small library of fragments obtained with our approach showed good versatility both in synthetic and physico-chemical properties.

Design, synthesis and biological activities of piperidine-spirooxadiazole derivatives as α7 nicotinic receptor antagonists

α: 7 nicotinic acetylcholine receptors (nAChRs) expressed in the nervous and immune systems have been suggested to play important roles in the control of inflammation. However, the lack of antagonist tools specifically inhibiting α7 nAChR impedes the validation of the channel as therapeutic target. To discover a selective α7 antagonist, we started a pharmacophore-based virtual screening and identified a piperidine-spirooxadiazole derivative T761–0184 that acts as a α7 antagonist. A series of novel piperidine-spirooxadiazole derivatives were subsequently synthesized and evaluated using two-electrode voltage clamp (TEVC) assay in Xenopus oocytes. Lead compounds from two series inhibited α7 with their IC50 values ranging from 3.3 μM to 13.7 μM. Compound B10 exhibited α7 selectivity over other α4β2 and α3β4 nAChR subtypes. The analysis of structure-activity relationship (SAR) provides valuable insights for further development of selective α7 nAChR antagonists.

Synthesis of 2,4-Disubstituted Imidazoles via Nucleophilic Catalysis

A convergent, microwave-assisted protocol for the synthesis of disubstituted NH-imidazoles via nucleophilic catalysis is described. The substituted imidazoles are accessed via the intramolecular addition of a variety of amidoxime substrates to activated a

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).

Discovery of 1,2,4-oxadiazole derivatives as a novel class of noncompetitive inhibitors of 3-hydroxykynurenine transaminase (HKT) from Aedes aegypti

The mosquito Aedes aegypti is the vector of arboviruses such as Zika, Chikungunya, dengue and yellow fever. These infectious diseases have a major impact on public health. The unavailability of effective vaccines or drugs to prevent or treat most of these

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.