5331-92-0

Basic information

• Product Name: 3,4-DICHLOROBENZALDEHYDE OXIME
• Synonyms: 3,4-DICHLOROBENZALDEHYDE OXIME;3,4-DICHLOROBENZALDOXIME;(NZ)-N-[(3,4-dichlorophenyl)methylidene]hydroxylamine
• CAS NO: 5331-92-0
• Molecular Formula: C₇H₅Cl₂NO
• Molecular Weight: 190.03
• EINECS: -0
• Mol File: 5331-92-0.mol

Chemical Properties

• Melting Point: 121-123°C
• Boiling Point: 278.2 °C at 760 mmHg
• Flash Point: 122.1 °C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 0.00207mmHg at 25°C
• Refractive Index: 1.575
• PKA: 10.22±0.10(Predicted)
• BRN: 2206792
• CAS DataBase Reference: 3,4-DICHLOROBENZALDEHYDE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DICHLOROBENZALDEHYDE OXIME(5331-92-0)
• EPA Substance Registry System: 3,4-DICHLOROBENZALDEHYDE OXIME(5331-92-0)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 5331-92-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3,4-Dichlorobenzaldehyde Oxime is used as an intermediate in the synthesis of various complex compounds. Its unique structure and functional groups make it a valuable component in the creation of a wide range of chemical products.
Used in Pharmaceutical Industry:
3,4-Dichlorobenzaldehyde Oxime is used as a building block in the development of pharmaceutical compounds. Its presence in the molecular structure can contribute to the overall properties and effectiveness of the final drug product.
Used in Agrochemical Industry:
3,4-Dichlorobenzaldehyde Oxime is used as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its role in these applications is to provide the necessary chemical structure for the active ingredients to be effective in controlling pests and weeds.
Used in Dye and Pigment Industry:
3,4-Dichlorobenzaldehyde Oxime is used as a starting material in the synthesis of dyes and pigments. Its chemical properties allow for the creation of a variety of colors and shades, which can be used in various industries such as textiles, plastics, and paints.
Used in Research and Development:
3,4-Dichlorobenzaldehyde Oxime is used as a research compound in academic and industrial laboratories. Its unique structure and reactivity make it an interesting subject for studies in organic chemistry, material science, and related fields.

InChI:InChI=1/C7H5Cl2NO/c8-6-2-1-5(4-10-11)3-7(6)9/h1-4,11H/b10-4+

Upstream product

• 6287-38-3 3,4-dichlorobenzaldehyde 

Downstream Products

• 6574-99-8 3,4-dichloro-benzonitrile 
• 28394-01-6 N-benzyl-3,4-dichlorobenzamide 
• 6208-35-1 3-(3,4-dichlorophenyl)-5-hydroxymethylisoxazole 
• 41421-27-6 5-(3,4-dichloro-phenyl)-1⁽²⁾H-tetrazole 
• 1056189-27-5 3,4-dichloro-N-hydroxybenzenecarboximidoyl chloride 
• 61101-08-4 3,4-Dichloro-benzaldehyde O-(2-cyclohexyloxy-4,6-dinitro-phenyl)-oxime 
• 13321-38-5 3,4-Dichloro-benzaldehyde O-(5-isopropylsulfanyl-2,4-dinitro-phenyl)-oxime 
• 13180-81-9 4-[1-(3,4-Dichloro-phenyl)-meth-(E)-ylideneaminooxy]-3-nitro-benzoic acid methyl ester 

Relevant articles and documents

The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water

The synthesis of oximes from aryl aldehydes was prepared using hydroxylamine hydrochloride. The obtained oxime compounds were synthesized at maximum efficiency in mineral water at room temperature. The developed method is economical, practical and environmentally friendly. All of the aldehydes were converted the oxime a method using local sources and useful for industrial applications is introduced in the literature. Graphic abstract: In this study, addition elimination reaction, one of the important reactions of organic chemistry, was carried out using local sources. With this reaction, aryl oximes were obtained from aryl aldehydes in mineral water under catalyst-free conditions.[Figure not available: see fulltext.]

HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids with arylaldehydes: one-pot synthesis of 1-arylisoquinolines

In this paper, a concise, open-vessel synthesis of 1-arylisoquinolines is describedviaHCl-mediated intermolecular cyclocondensation of oxygenated arylacetic acids with arylaldehydes in the presence of NH2OH and alcoholic solvents under mild and one-pot reaction conditions. A plausible mechanism is proposed and discussed herein. In the overall reaction process, only water was generated as the byproduct. Various environmentally friendly reaction conditions are investigated for convenient transformationviathe (4C + 1C + 1N) annulation. This protocol provides a highly effective ring closureviathe formations of one carbon-carbon (C-C) bond, two carbon-nitrogen (C-N) bonds and one carbon-oxygen (C-O) bond.

Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis

Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.

Cu(II)–metformin immobilized on graphene oxide: an efficient and recyclable catalyst for the Beckmann rearrangement

Abstract: In this study, for the first time, the copper(II) nanoparticles (NPs) have been immobilized on metformin-functionalized graphene oxide and then its catalytic applications have been investigated in synthesis of amides from aldoximes (Beckmann rearrangement). The chemical structure of prepared catalyst has been characterized by various analyses like FT-IR, TGA, TEM, SEM, EDX, and ICP. All analyses confirm the successful and stable immobilization of copper NPs on functionalized graphene oxide. This synthesized heterogeneous nanocatalyst showed excellent catalytic activity with high product yields and short reaction times. Also, the suggested catalyst could be recycled ten times without a drastic decrease in its catalytic activity. Graphic abstract: [Figure not available: see fulltext.].

Design, synthesis of novel 4,5-dihydroisoxazole-containing benzamide derivatives as highly potent FtsZ inhibitors capable of killing a variety of MDR Staphylococcus aureus

Antibiotic resistance among clinically significant bacterial pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. As a part of continuing effort to develop antibacterial agents, we rationally designed and synthesized two series of 4,5-dihydroisoxazol-5-yl and 4,5-dihydroisoxazol-3-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compound A16 possessing the 4,5-dihydroisoxazol-5-yl group showed outstanding antibacterial activity (MIC, ≤0.125–0.5 μg/mL) against various testing strains, including methicillin-resistant, penicillin-resistant and clinical isolated S. aureus strains. Besides, further mouse infection model revealed that A16 could be effective in vivo and non-toxic to Hela cells. Finally, a detailed discussion of structure-activity relationships was conducted, referring to the docking results. It is worth noting that substituting a 4,5-dihydroisoxazole ring for the isoxazole ring not only broadened the antibacterial spectrum but also resulted in a significant increase in antibacterial activity against S. aureus strains. Taken together, these results suggest a promising chemotype for the development of new FtsZ-targeting bactericidal agents.

Discovery of Natural Product-Based Fungicides (II): Semisynthesis and Biological Activity of Sarisan Attached 3-Phenylisoxazolines as Antifungal Agents

Many phytopathogenic fungi cause severe damage to crop yields. In continuation of our research aimed at the discovery and development of natural products-based fungicides, a series of thirty-one sarisan attached 3-phenylisoxazolines were synthesized and evaluated for their antifungal activities against five phytopathogenic fungi (B. cinerea, C. lagenarium, A. solani, F. solani, and F. graminearum). Among all title sarisan derivatives, compounds IV2, IV14 and IV23 showed potent antifungal activity against some phytopathogenic fungi. In particular, compound IV2 exhibited a broad-spectrum and more potent antifungal activity against A. solani, F. solani, and F. graminearum than the commercial fungicide Hymexazol. In addition, compounds IV2, IV14 and IV23 also displayed relative low toxicity on normal NRK-52E cells. This work will give some insights into the development of sarisan derivatives as new fungicide candidates in plant protection.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Design, docking and synthesis of novel bromo isatin incorporated isoxazole derivatives as vegfr-2 inhibitors

Objective: To design, synthesize, in vitro Vascular Endothelial Growth Factor Receptor (VEGFR-2) assay, antiproliferative activity an Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) studies of some novel bromoisatin incorporated isoxa

Synthesis and biological evaluation of novel 1-(aryl-aldehyde-oxime)uracil derivatives as a new class of thymidine phosphorylase inhibitors

A novel series of 1-(aryl aldehyd oxime) uracil derivatives were synthesized, characterized and evaluated for its inhibitory activity against thymidine phosphorylase. Among them, the compound 8d, 8e, 8f, 8g and 8l displayed potent thymidine phosphorylase

Novel design of recyclable copper(II) complex supported on magnetic nanoparticles as active catalyst for Beckmann rearrangement in poly(ethylene glycol)

Copper complex-functionalized magnetic core–shell nanoparticles (Fe3O4@SiO2-Lig-Cu) were prepared and characterized using various techniques. The activity of the new catalyst was tested for the Beckmann rearrangement. The reaction conditions allow for the conversion of a wide variety of aldoximes, including aromatic and heterocyclic ones, to amides in good to excellent yields. High efficiency, mild reaction conditions, easy work-up, use of poly(ethylene glycol) as a green medium and simple purification of products are important advantages of this system. Moreover, the eco-friendly heterogeneous nanocatalyst could be easily recovered from the reaction mixture using an external magnet and reused several times.