3376-23-6

Basic information

• Product Name: N-Oxylato-N-benzylidenemethanaminium
• Synonyms: Methylbenzylideneoxylatoiminium;N-(Phenylmethylene)methanamine oxide;N-Benzylidenemethanamine oxide;N-Methyl-N-oxylatobenzylideneiminium;N-Oxylato-N-benzylidenemethanaminium;α-Phenyl-N-methylnitron;methanamine, N-(phenylmethylene)-, N-oxide
• CAS NO: 3376-23-6
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16316
• Mol File: 3376-23-6.mol

Chemical Properties

• Boiling Point: 250°Cat760mmHg
• Flash Point: 113.8°C
• Appearance: /
• Density: 1.044g/cm³
• Vapor Pressure: 0.0351mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: N-Oxylato-N-benzylidenemethanaminium(CAS DataBase Reference)
• NIST Chemistry Reference: N-Oxylato-N-benzylidenemethanaminium(3376-23-6)
• EPA Substance Registry System: N-Oxylato-N-benzylidenemethanaminium(3376-23-6)

Safety Data

• Hazardous Substances Data: 3376-23-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 50, p. 12185, 1994 DOI: 10.1016/S0040-4020(01)89569-7Tetrahedron Letters, 26, p. 4331, 1985 DOI: 10.1016/S0040-4039(00)98726-4

InChI:InChI=1/C8H9NO/c1-9(10)7-8-5-3-2-4-6-8/h2-7H,1H3

Upstream product

• 593-77-1 N-Methylhydroxylamine 
• 100-52-7 benzaldehyde 
• 932-90-1 syn-benzaldehyde oxime 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 622-32-2 (Z)-benzaldehyde oxime 
• 124-41-4 sodium methylate 
• 75-52-5 nitromethane 
• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 103-67-3 benzyl-methyl-amine 
• 7445-60-5 bis(trifluoromethyl)thioketene 
• 1569-76-2 N-methoxy-α-phenylnitrone 
• 1589-82-8 phenylmagnesium bromide 
• 36324-57-9 (E)-N-(1-phenylethylidene)methanamine N-oxide 

Downstream Products

• 88070-48-8 N-methylbenzamide 
• 1028-26-8 2-methyl-3,4-diphenyl-[1,2,4]oxadiazolidin-5-one 
• 593-77-1 N-Methylhydroxylamine 
• 100-52-7 benzaldehyde 
• 100-47-0 benzonitrile 
• 3555-72-4 N-benzyl-N-methylhydroxylamine 
• 99-61-6 3-nitro-benzaldehyde 
• 16089-77-3 N-methyl-α-(m-nitrophenyl)nitrone 
• 21355-14-6 (4-bromo-phenyl)-(2-methyl-3,4,4-triphenyl-isoxazolidin-5-ylidene)-amine 
• 51289-46-4 4-ethyl-2-methyl-3-phenyl-5-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-[1,2,4]oxadiazolidine 
• 51254-10-5 4-(4-methoxy-phenyl)-2-methyl-3-phenyl-5-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-[1,2,4]oxadiazolidine 
• 51254-08-1 2-methyl-3,4-diphenyl-5-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-[1,2,4]oxadiazolidine 
• 35887-94-6 2-methyl-3c-phenyl-(3ac,3bt,7at,7bc)-2,3,3a,3b,4,7,7a,7b-octahydro-4r,7c-etheno-benzo[3,4]cyclobuta[1,2-d]isoxazole-5,6-dicarboxylic acid dimethyl ester 
• 36001-35-1 2-methyl-3ξ-phenyl-(3at,4ac,6ac,7at)-2,3,3a,4,4a,6a,7,7a-octahydro-4r,7c-etheno-cyclobuta[4,5]benzo[1,2-d]isoxazole-8,9-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Regio- and stereoselective synthesis of novel isoxazolidine heterocycles by 1,3-dipolar cycloaddition between C-phenyl- N -methylnitrone and substituted alkenes. Experimental and DFT investigation of selectivity and mechanism

A series of isoxazolidine heterocycles was synthesized through the 1,3-dipolar cycloaddition (13DC) reaction of C-phenyl-N-methylnitrone with different substituted alkenes. The structures and stereochemistry of the cycloadducts were determined by spectroscopic methods. These 13DC reactions are characterized by complete regioselectivity and high stereoselectivity. The molecular mechanism, reactivity and selectivity of these 13DC reactions have been investigated by means of transition state theory and reactivity indices derived from conceptual DFT using DFT methods at the B3LYP/6-31G(d,p) level of theory. The obtained results indicate that these cycloaddition reactions take place through a one-step synchronous mechanism with a non-polar mechanism and high activation energies. The theoretical results are in agreement with the experimental findings.

S -Tetrazine: Robust and Green Photoorganocatalyst for Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones

Efficient photocatalytic aerobic oxidative dehydrogenation reactions of N,N-disubstituted hydroxylamines to nitrones were developed with an in situ generated photocatalyst based on commercially available 3,6-dichlorotetrazine. This process affords a wide range of nitrones in high yields under mild conditions. In addition, an oxidative (3+3) cycloaddition between an oxyallyl cation precursor and a hydroxylamine was also developed.

Regio- and Enantioselective (3+3) Cycloaddition of Nitrones with 2-Indolylmethanols Enabled by Cooperative Organocatalysis

The regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols was accomplished by the cooperative catalysis of hexafluoroisopropanol (HFIP) and chiral phosphoric acid (CPA). Using this approach, a series of indole-fused six-membered heterocycles were synthesized in high yields (up to 98 %), with excellent enantioselectivities (up to 96 % ee) and exclusive regiospecificity. This approach enabled not only the first organocatalytic asymmetric (3+3) cycloaddition of nitrones but also the first C3-nucleophilic asymmetric (3+3) cycloaddition of 2-indolylmethanols. More importantly, theoretical calculations elucidated the role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction, demonstrating a new mode of cooperative catalysis.

Carbamoylation of Azomethine Imines via Visible-Light Photoredox Catalysis

A versatile and robust photocatalytic methodology to install the amide functional group into azomethine imine ions is described. This protocol is distinguished by its broad scope and mild reaction conditions, which are well suited for the preparation of s

Cucurbit[7]uril as a catalytic nanoreactor for one-pot synthesis of isoxazolidines in water

The main objective of supramolecular chemistry is to mimic the macrosystems present in nature, a goal that fits perfectly with the green chemistry guidelines. The aim of our work is to use the hydrophobic cavity of cucurbit[7]uril (CB[7]) to mimic nature

Nucleophilic Addition to Nitrones Using a Flow Microreactor

Nucleophilic addition reactions of soft carbon nucleophiles to nitrones in a flow microreactor are reported for the first time. Under microflow conditions at 30 to 0 °C, a range of nitrones can be efficiently transformed into the corresponding oxyiminium ions by reaction with either acyl halides or trialkylsilyl triflates. These can subsequently undergo the addition of nucleophiles including allyltributylstannane, ketene methyl tert-butyldimethylsilyl acetal, and N-silyl ketene imines to afford the corresponding adducts in high yields; such reactions at a similar temperature under batch conditions resulted in lower yields because of undesired side reactions.

Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones with carbodiimides

An efficient [3+2] cycloaddition of nitrones and carbodiimides has been developed. This 1,3-dipolar cycloaddition features high regioselectivity, mild and metal-free conditions, excellent functional group compatibility, and a broad substrate scope. The X-ray structures of two regio-isomers confirmed the regioselectivity of this transformation.

A green synthesis of nitrones in glycerol

Abstract: An eco-friendly and efficient synthesis of nitrones is presented by condensation of an equimolar amount of aldehydes and N-substituted hydroxylamine hydrochlorides in glycerol as a recyclable solvent-catalyst. This novel protocol provides rapid and mild access to a series of nitrone derivatives in good to excellent yields in the absence of catalyst and base. Graphic abstract: SYNOPSIS In this study, a base-free protocol by using glycerol as the solvent-catalyst was applied for an eco-friendly synthesis of nitrones from the condensation of aldehydes and N-substituted hydroxylaminehydrochlorides.[Figure not available: see fulltext.].

BPh3-Catalyzed [2+3] Cycloaddition of Ph3PCCO with Aldonitrones: Access to 5-Isoxazolidinones with Exocyclic Phosphonium Ylide Moieties

A method for the generation of 5-isoxazolidinones with exocyclic phosphonium ylide functionalities via [2+3] cycloaddition of Ph3PCCO and aldonitrones has been developed and applied in the synthesis of 4-alkylidene-5-isoxazolidinones via Wittig olefination. The reaction proceeds by BPh3 catalysis under mild conditions and with a broad substrate scope. A reaction pathway involving the activation of the aldonitrone via interactions with the Lewis acid BPh3 is proposed.

MICROBIOCIDAL PICOLINAMIDE DERIVATIVES

Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, and especially fungicides.