3717-15-5

Basic information

• Product Name: (αE)-N-Hydroxy-4-methylbenzenemethaneimine
• Synonyms: (E)-4-Methylbenzaldehyde oxime;(E)-p-Tolualdehyde oxime;(αE)-N-Hydroxy-4-methylbenzenemethaneimine;syn-p-Tolualdoxime;(NE)-N-[(4-methylphenyl)methylidene]hydroxylamine
• CAS NO: 3717-15-5
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.1632
• Mol File: 3717-15-5.mol
• Article Data: 150

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 216.8°Cat760mmHg
• Flash Point: 116.4°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 0.0804mmHg at 25°C
• Refractive Index: 1.518
• PKA: 10.83±0.10(Predicted)
• CAS DataBase Reference: (αE)-N-Hydroxy-4-methylbenzenemethaneimine(CAS DataBase Reference)
• NIST Chemistry Reference: (αE)-N-Hydroxy-4-methylbenzenemethaneimine(3717-15-5)
• EPA Substance Registry System: (αE)-N-Hydroxy-4-methylbenzenemethaneimine(3717-15-5)

Safety Data

• Hazardous Substances Data: 3717-15-5(Hazardous Substances Data)

Usage

Description

(αE)-N-Hydroxy-4-methylbenzenemethaneimine, also known as 4-methylbenzylhydroxylamine, is an organic compound with the chemical formula C8H11NO. It is an important intermediate in the production of pharmaceuticals and agrochemicals, as well as a potential precursor for the synthesis of various other organic compounds. This chemical is also known for its ability to act as a chelating agent, which means it can bind to metal ions and form stable complexes. Its unique structure and properties make it a valuable compound in organic synthesis and chemical research.

Uses

Used in Pharmaceutical and Agrochemical Production:
(αE)-N-Hydroxy-4-methylbenzenemethaneimine is used as an intermediate for the synthesis of various pharmaceuticals and agrochemicals due to its versatile chemical properties and reactivity.
Used in Organic Synthesis:
(αE)-N-Hydroxy-4-methylbenzenemethaneimine is used as a valuable compound in organic synthesis for its unique structure and properties, which allow for the creation of a wide range of other organic compounds.
Used in Rubber and Plastic Manufacturing:
(αE)-N-Hydroxy-4-methylbenzenemethaneimine is used as a component in the manufacturing of various rubber and plastic products, contributing to their overall properties and performance.
Used as a Chelating Agent:
(αE)-N-Hydroxy-4-methylbenzenemethaneimine is used as a chelating agent for its ability to bind to metal ions and form stable complexes, which can be beneficial in various chemical processes and applications.
Used in the Synthesis of Antioxidants and Corrosion Inhibitors:
(αE)-N-Hydroxy-4-methylbenzenemethaneimine is used as a precursor in the synthesis of antioxidants and corrosion inhibitors, where its chelating properties can enhance the performance of these additives in various industrial applications.

InChI:InChI=1/C8H9NO/c1-7-2-4-8(5-3-7)6-9-10/h2-6,10H,1H3/b9-6-

Upstream product

• 104-84-7 para-methylbenzylamine 
• 2826-25-7 2-(4-methylbenzylidene)malononitrile 
• 589-18-4 4-Methylbenzyl alcohol 
• 106-49-0 p-toluidine 
• 6639-47-0 1,3,5-tris(p-tolyl)hexahydro-s-triazine 
• 104-87-0 4-methyl-benzaldehyde 
• 92114-96-0 mercury fulminate 
• 108-88-3 toluene 
• 590-28-3 potassium cyanate 
• 3717-16-6 (Z)-4-methylbenzaldehyde oxime 
• 2168-80-1 4-methyldithioic acid 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 104-81-4 4-Methylbenzyl bromide 
• 106-38-7 para-bromotoluene 

Downstream Products

• 958836-72-1 2-(4-chlorophenyl)-5-(5-methyl-3-p-tolyl-4,5-dihydroisoxazol-5-yl)-1,3,4-oxadiazole 
• 1014403-49-6 2-(5-methyl-3-p-tolyl-4,5-dihydroisoxazol-5-yl)-5-phenyl-1,3,4-oxadiazole 
• 134378-95-3 3-(4-methylphenyl)isoxazole-5-carboxylic acid 
• 1334686-98-4 N,N-di-n-hexyl-3-(4-methylphenyl)isoxazole-5-carboxamide 
• 1278561-46-8 (E)-4-methylbenzaldehyde O-4-methoxybenzoyl oxime 
• 3424-93-9 4-methoxyphenylacetamide 
• 104-85-8 para-methylbenzonitrile 
• 619-55-6 para-methylbenzamide 
• 1222194-58-2 5-methyl-3-(4-methylphenyl)-5-phenyl-1,4,2-dioxazole 
• 1337539-52-2 C₂₇H₃₄N₄O 
• 1337539-58-8 C₂₇H₃₃FN₄O 
• 1337539-66-8 C₂₇H₃₃ClN₄O 
• 1222194-57-1 5-(4-methoxy-phenyl)-3-(4-methylphenyl)-1,4,2-dioxazole 
• 1220346-14-4 (E)-4-methylbenzaldehyde O-(E)-1,3-bis(4-chlorophenyl)allyl oxime 

Relevant articles and documents

Nickel-Catalyzed NO Group Transfer Coupled with NOxConversion

Nitrogen oxide (NOx) conversion is an important process for balancing the global nitrogen cycle. Distinct from the biological NOx transformation, we have devised a synthetic approach to this issue by utilizing a bifunctional metal catalyst for producing value-added products from NOx. Here, we present a novel catalysis based on a Ni pincer system, effectively converting Ni-NOx to Ni-NO via deoxygenation with CO(g). This is followed by transfer of the in situ generated nitroso group to organic substrates, which favorably occurs at the flattened Ni(I)-NO site via its nucleophilic reaction. Successful catalytic production of oximes from benzyl halides using NaNO2 is presented with a turnover number of >200 under mild conditions. In a key step of the catalysis, a nickel(I)-?NO species effectively activates alkyl halides, which is carefully evaluated by both experimental and theoretical methods. Our nickel catalyst effectively fulfills a dual purpose, namely, deoxygenating NOx anions and catalyzing C-N coupling.

On the mixed oxides-supported niobium catalyst towards benzylamine oxidation

A series of mixed oxides-supported niobium-based catalysts has been synthesized and applied towards oxidation reactions of benzylamine derivatives. Under the optimized reaction conditions, the selectivity to oxime enhanced, leading to the main product with up to 72 %. Moreover, even α-substituted benzylamines were well tolerated and led to oximes in good isolated yields. It is important to mention; four equivalents of the harmless and inexpensive hydrogen peroxide were employed as oxidizing agent. Mechanism hypothesis suggested that the reaction proceed to selective benzylamine oxidation into nitroso intermediate, following by formation of the corresponding oxime tautomer mediated by an unstable water produced by NbOx supported catalyst. This consists the first mixed oxides-supported niobium-based catalyst for selective oxidation of benzylamines to oximes.

Poly(N-vinylimidazole): A biocompatible and biodegradable functional polymer, metal-free, and highly recyclable heterogeneous catalyst for the mechanochemical synthesis of oximes

The catalytic activity of poly(N-vinylimidazole), a biocompatible and biodegradable synthetic functional polymer, was investigated for the synthesis of oximes as an efficient, halogen-free, and reusable heterogeneous catalyst. The corresponding oximes were afforded in high to excellent yields at room temperature and in short times using the planetary ball mill technique. Some merits, such as the short reaction times and good yields for poorly active carbonyl compounds, and avoiding toxic, expensive, metal-containing catalysts, and hazardous and flammable solvents, can be mentioned for the current catalytic synthesis of the oximes. Furthermore, the heterogeneous organocatalyst could be easily separated after the reaction, and the regenerated catalyst was reused several times with no significant loss of its catalytic activity.