3848-36-0

Basic information

• Product Name: 4-CHLOROBENZALDEHYDE OXIME
• Synonyms: AKOS B004078;4-CHLOROBENZALDEHYDE OXIME;4-CHLOROBENZALDOXIME;4-CHLOROBENZENECARBALDEHYDE OXIME;N-(4-Chlorobenzylidene)hydroxylamine;benzaldehyde, 4-chloro-, oxime
• CAS NO: 3848-36-0
• Molecular Formula: C₇H₆ClNO
• Molecular Weight: 155.58
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 3848-36-0.mol

Chemical Properties

• Melting Point: 108-110°C
• Boiling Point: 233.2 °C at 760 mmHg
• Flash Point: 94.8 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 0.0314mmHg at 25°C
• Refractive Index: 1.55
• PKA: 10.45±0.10(Predicted)
• CAS DataBase Reference: 4-CHLOROBENZALDEHYDE OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBENZALDEHYDE OXIME(3848-36-0)
• EPA Substance Registry System: 4-CHLOROBENZALDEHYDE OXIME(3848-36-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 3848-36-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
4-Chlorobenzaldehyde Oxime is used as a chemical intermediate for the synthesis of various organic compounds and pharmaceuticals. Its unique structure with a chloro and oxime group allows it to participate in a range of chemical reactions, making it a valuable component in the development of new chemical entities.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 4-Chlorobenzaldehyde Oxime serves as a key intermediate in the production of certain drugs. Its reactivity and functional groups enable the creation of diverse medicinal compounds with potential therapeutic applications.
Used in Research and Development:
4-Chlorobenzaldehyde Oxime is also utilized in research laboratories for the study of chemical reactions and mechanisms involving aromatic compounds. Its unique properties make it an interesting subject for scientific investigations, potentially leading to new discoveries and applications in various fields.

InChI:InChI=1/C7H6ClNO/c8-7-3-1-6(2-4-7)5-9-10/h1-5,10H

Upstream product

• 110-89-4 piperidine 
• 119991-09-2 4-Chloro-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 2403-54-5 2-(4-chlorophenyl)-1,3-dioxolane 
• 25370-09-6 dibenzylcarbamyl chloride 
• 89970-60-5 C₇H₆ClN₂O₂^(1-)*Na⁽¹⁺⁾ 
• 104-88-1 4-chlorobenzaldehyde 
• 91757-32-3 3-(4-Chloro-phenyl)-5-phenyl-4,5-dihydro-[1,2,4]oxadiazin-6-one 
• 108-91-8 cyclohexylamine 
• 30866-47-8 N-(2-iminochromen-3-carbonyl)-N'-(4-chlorobenzylidene)carbohydrazide 
• 75605-57-1 N'-(4-chlorobenzylidene)-2-hydroxyiminochromen-3-carbohydrazide 
• 74-89-5 methylamine 
• 104-86-9 4-chlorobenzylamine 
• 873-76-7 para-Chlorobenzyl alcohol 
• 5470-11-1 hydroxylamine hydrochloride 

Downstream Products

• 52540-33-7 p-Chlor-benzaldehydoxim-diethylorthoacetat 
• 34768-54-2 C₁₄H₁₇ClN₂O₂ 
• 71059-53-5 O--p-chlor-benzaldoxim 
• 52540-32-6 p-Chlor-benzaldehydoxim-diethylorthoformiat 
• 13181-85-6 4-Chloro-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 19957-27-8 O-(1-Naphthylcarbamoyl)-p-chlorbenzaldoxim 
• 13180-80-8 4-[1-(4-Chloro-phenyl)-meth-(E)-ylideneaminooxy]-3-nitro-benzoic acid methyl ester 
• 34755-71-0 C₂₀H₃₁ClN₂O₂ 
• 13180-86-4 2-[1-(4-Chloro-phenyl)-meth-(Z)-ylideneaminooxy]-3,5-dinitro-benzoic acid methyl ester 
• 54222-79-6 C₁₆H₁₆Cl₂N₂O₂Si 
• 1822-97-5 3-(4-chlorophenyl)-5-(trichloromethyl)-1,2,4-oxadiazole 
• 28123-63-9 4-chlorobenzohydroximoyl chloride 
• 51307-68-7 N-4-chlorobenzylhydroxylamine 
• 26218-72-4 3,4-bis-(4-chloro-phenyl)-furazan 2-oxide 

Relevant articles and documents

A catalytic regioselective procedure for the synthesis of aryl oximes in the presence of palladium nanoparticles

The synthesis of aryl oximes from aryl aldehyde derivatives was carried out using hydroxylamine hydrochloride and aluminum oxy hydroxide-supported palladium (Pd/AlO(OH) nanoparticles. The procedure is revealed via the regioselective synthesis of oxime der

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.

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.]

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.

Design, synthesis and biological evaluation of novel indanone containing spiroisoxazoline derivatives with selective COX-2 inhibition as anticancer agents

Objective: A new family of 3′-(Mono, di or tri-substituted phenyl)-4′-(4-(methylsulfonyl) phenyl) spiroisoxazoline derivatives containing indanone spirobridge was designed, synthesized, and evaluated for their selective COX-2 inhibitory potency and cytotoxicity on different cell lines. Methods: A synthetic reaction based on 1,3-dipolar cycloaddition mechanism was applied for the regiospecific formation of various spiroisoxazolines. The activity of the newly synthesized compounds was determined using in vitro cyclooxygenase inhibition assay. The toxicity of the compounds was evaluated by MTT assay. In addition, induction of apoptosis, and expression levels of Bax, Bcl-2 and caspase-3 mRNA in MCF-7 cells were evaluated following exposure to compound 9f. The docking calculations and molecular dynamics simulation were performed to study the most probable modes of interactions of compound 9f upon binding to COX-2 enzyme. Results: The docking results showed that the synthesized compounds were able to form hydrogen bonds with COX-2 involving methyl sulfonyl, spiroisoxazoline, meta-methoxy and fluoro functional groups. Spiroisoxazoline derivatives containing methoxy group at the C-3′ phenyl ring meta position (9f and 9g) showed superior selectivity with higher potency of inhibiting COX-2 enzyme. Furthermore, compound 9f, which possesses 3,4-dimethoxyphenyl on C-3′ carbon atom of isoxazoline ring, exhibited the highest COX-2 inhibitory activity, and also displayed the most potent cytotoxicity on MCF-7 cells with an IC50 value of 0.03 ± 0.01 μM, comparable with that of doxorubicin (IC50 of 0.062 ± 0.012 μM). The results indicated that compound 9f could promote apoptosis. Also, compared to the control group, the mRNA expression of Bax and caspase-3 significantly increased, while that of Bcl-2 significantly decreased upon exposure to compound 9f which may propose the activation of mitochondrial-associated pathway as the mechanism of observed apoptosis. Conclusion: In vitro biological evaluations accompanied with in silico studies revealed that indanone tricyclic spiroisoxazoline derivatives are good candidates for the development of new anti-inflammatory and anticancer (colorectal and breast) agents.

Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B

A library of new spiroisoxazoline analogues of arteannuin B was synthesized through 1, 3-dipolar cycloaddition in stereoselective fashion and consequently screened for anti-inflammatory activity in RAW 264.7 macrophage cells. Three potent analogues (8i, 8 m, and 8n) were found to attenuate the LPS induced release of cytokines IL-6 and TNF-α more potently than the parent molecule. Also, the inhibition of LPS induced nitric oxide production in these cells show moderate to high efficacy. None of the three potent molecules have altered the viability of RAW 264.7 cells following 48 h incubation suggesting that the inhibition of cytokines and nitric oxide production exhibited in the cells was not due to toxicity. In addition, these compounds exhibit an IC50 range of 0.17 μM-1.57 μM and 0.09 μM-0.35 μM for the inhibition of IL-6 release and nitric oxide production respectively. The results disclose potent inhibition of pro-inflammatory mediators which are encouraging and warrant further investigations to develop new therapeutic agents for inflammatory diseases.

A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones

A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction mechanism for this reaction has also been proposed.

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.

Microwave synthesis method of benzaldoxime compounds

The invention discloses a microwave synthesis method of benzaldoxime compounds. The method comprises the following steps: dissolving a substituted benzaldehyde, hydroxylamine hydrochloride and an alkaline compound in an organic solvent, placing the formed solution in a microwave reaction kettle for a reaction, spin-drying the solvent after the reaction is finished, conducting mixed extraction withethyl acetate and water, separating an organic phase, carrying out drying with anhydrous sodium sulfate, and successively performing filtering and desolventizing to obtain a benzaldoxime compound. Based on the structure of the substituted benzaldehyde, the substituted benzaldoxime compound is obtained by reacting the aldehyde with hydroxylamine hydrochloride in the microwave reaction kettle. Themethod is simple in process, convenient to operate, short in reaction time and high in yield, meets the requirement for environment friendliness and improves economic benefits.

Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate

Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.