28123-63-9

Basic information

• Product Name: Alpha-Chloro-4-Chloro-Benzaldoxime
• Synonyms: Alpha-Chloro-4-Chloro-Benzaldoxime;alpha,4-Dichlorobenzaldoxime;alpha,4-Dichlorobenzaldoxime95+%
• CAS NO: 28123-63-9
• Molecular Formula: C₇H₅Cl₂NO
• Molecular Weight: 190.0267
• Mol File: 28123-63-9.mol

Chemical Properties

• Melting Point: 87-88°
• Boiling Point: 304.8±44.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• PKA: 10.22±0.70(Predicted)
• CAS DataBase Reference: Alpha-Chloro-4-Chloro-Benzaldoxime(CAS DataBase Reference)
• NIST Chemistry Reference: Alpha-Chloro-4-Chloro-Benzaldoxime(28123-63-9)
• EPA Substance Registry System: Alpha-Chloro-4-Chloro-Benzaldoxime(28123-63-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 28123-63-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Alpha-Chloro-4-Chloro-Benzaldoxime is utilized as a key component in organic synthesis, contributing to the formation of complex organic molecules. Its unique structure allows it to participate in a variety of chemical reactions, making it a valuable asset in the synthesis of new compounds.
Used in Chemical Reactions as a Reagent:
In chemical reactions, Alpha-Chloro-4-Chloro-Benzaldoxime serves as a reagent, facilitating specific transformations and providing a pathway for desired chemical outcomes. Its presence can influence the course of reactions, leading to the production of desired products.
Used in Pharmaceutical Production as an Intermediate:
Alpha-Chloro-4-Chloro-Benzaldoxime is recognized for its potential application as an intermediate in the production of pharmaceuticals. Its involvement in the synthesis of drug molecules can contribute to the development of new medications and therapies.
Used in Agrochemical Production as an Intermediate:
Similarly, in the agrochemical industry, Alpha-Chloro-4-Chloro-Benzaldoxime is employed as an intermediate. Its role in the synthesis of agrochemicals can lead to the creation of new products for agricultural applications, such as pesticides and herbicides.

Upstream product

• 3848-36-0 4-chlorobenzaldoxime 
• 104-88-1 4-chlorobenzaldehyde 
• 459-23-4 4-fluorobenzaldoxime 
• 3717-24-6 4-chlorobenzaldehyde oxime 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 97026-71-6 (3-(4-chlorophenyl)-5-methyl)isoxazole-4-carboxylic acid ethyl ester 
• 37737-85-2 3-(4-chloro-phenyl)-5-methylsulfanyl-5-naphthalen-1-yl-[1,4,2]oxathiazole 
• 14688-30-3 3,5-di(p-chlorophenyl)isoxazole 
• 98147-16-1 3-(4-chloro-phenyl)-6a-piperidin-1-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole 
• 98222-46-9 3-(4-chloro-phenyl)-6a-morpholin-4-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole 
• 31301-39-0 3-(4-chlorophenyl)-isoxazole 
• 31554-57-1 5-(4-bromo-phenyl)-3-(4-chloro-phenyl)-isoxazole 
• 14735-11-6 1-{3-[3-(4-chloro-phenyl)-isoxazol-5-yl]-propyl}-piperidine 
• 98347-52-5 3-(4-chloro-phenyl)-4-cyclohexyl-5-propyl-4,5-dihydro-[1,2,4]oxadiazole 
• 24097-17-4 3-(4-chlorophenyl)-5-phenylisoxazole 
• 54252-34-5 3-(4-chloro-phenyl)-4-nitro-5-pyrrolidin-1-yl-isoxazole 
• 13157-40-9 [3-(4-chloro-phenyl)-[1,4,2]oxathiazol-5-ylidene]-malononitrile 
• 13157-41-0 [3-(4-chloro-phenyl)-[1,4,2]oxathiazol-5-ylidene]-cyano-acetic acid methyl ester 
• 65729-40-0 4-[3-(4-chloro-phenyl)-4-p-tolyl-4,5-dihydro-[1,2,4]oxadiazol-5-yl]-2-methoxy-phenol 

Relevant articles and documents

Synthesis, characterization, antimicrobial activity, and QSAR studies of some new 6-substituted phenyl 3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino [5,6-d]isoxazoles

3-(4-Chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino[5,6-d] isoxazoles were synthesized from the reaction of (3-(4-chlorophenyl)-4,5-dihydroisoxazole-4,5-diyl)dimethanol with substituted phenylboronic acids. Crystal structure of 1-(4-(3-(4-chlorophenyl)-3a,4,8,8a-tetrahydro-[1,3,2]dioxaborepino[5,6-d]isoxazol-6-yl)phenyl) ethanone was studied and the values of selected bond distances (?), bond angles (°), and dihedral angles (°) were found in agreement with the calculated (DFT, B3LYP/6-311++G(d,p)) values. Antimicrobial activity of these new compounds was also studied against a panel of microorganisms including Staphylococcus aureus, Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, Streptococcus mutans, and Candida albicans. Most of the dioxaborepines exhibited fair activities against these microorganisms. The pMIC values of the compounds were first correlated with Hammett polar substituent constant (σ) together with lipophilic constant (π) and statistically significant 2D correlations were obtained. In addition, the pMIC values of the compounds were correlated with some theoretical descriptors and fair 2D-QSAR models with clogP, SAA, and μ as independent variables were obtained.

Three-component synthesis and 1,3-dipolar cycloaddition of highly functionalized pyrans with nitrile oxides: Easy access to 1,2,4-oxadiazoles

Three-component reaction of 1-[(4-chlorophenyl)sulfanyl]acetone, malononitrile, and substituted aromatic aldehydes in the presence of sodium ethoxide under simple mixing at ambient temperature for 5-8 min afforded highly functionalized 4H-pyrans in good t

N-Allyl-substituted aminomethylene-1,1-bisphosphonates in 1,3-dipolar cycloaddition reaction with aromatic nitrile N-oxides

A reaction of N-allyl-substituted aminomethylene-1,1-bisphosphonates with aromatic nitrile N-oxides was used to obtain new aminomethylenebisphosphonates with one or two 3-arylisoxazoline rings at the nitrogen atom. NMR spectroscopy studies showed that the

Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction

A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.

Design, synthesis, in vitro and in silico evaluation of new 3-phenyl-4,5-dihydroisoxazole-5-carboxamides active against drug-resistant mycobacterium tuberculosis

A new series of 3-phenyl-4,5-dihydroisoxazole-5-carboxamides were designed, synthesized, and evaluated for their potency against Mtb H37Rv. Designed molecules were synthesized by one-pot cycloaddition reaction in good to excellent yields. Anti-Tubercular evaluation of all synthesized derivatives identified 6k to be highly potent (MIC 1 μg/mL) against Mtb and drug-resistant strains. All potent derivatives were found to be non-toxic when tested against Vero cells. Also, in silico studies were employed to explore the binding patterns of designed compounds to target Mycobacterial membrane protein Large-3. All derivatives exhibited excellent binding patterns with the receptor. The excellent in silico Absorption, Distribution, Metabolism, and Excretion properties and druggability parameters positions these molecules as promising lead candidates for the future development of new drugs to treat drug-resistant Tuberculosis.

Synthesis and biological evaluation of novel isoxazole derivatives from acridone

The present study was carried out in an?attempt to synthesize a new class of potential antibacterial agents. In this context, novel isoxazoles were synthesized and evaluated for their potential antibacterial behavior against four pathogenic bacterial strains. The synthesized compounds exhibited moderate-to-good antibacterial activity against these strains. The highest antibacterial activity was observed against the Escherichia coli strains, particularly for compounds 4a and 4e with phenyl and para-nitrophenyl groups on the isoxazole–acridone skeleton;?they showed promising minimum inhibitory concentration values of 16.88 and 19.01 μg/ml, respectively, compared with the standard drug chloramphenicol (22.41 μg/ml). The synthesized compounds were subjected to in silico docking studies to understand the mode of their interactions with the DNA topoisomerase complex (PDB ID: 3FV5) of E. coli. The molecular docking results showed that compounds 4a–l occupy the active site of DNA topoisomerase (PDB ID: 3FV5), stabilized via hydrogen bonding and hydrophobic interactions, which may be the reason behind their interesting in vitro antibacterial activity.

Ru-Catalyzed [3 + 2] Cycloaddition of Nitrile Oxides and Electron-Rich Alkynes with Reversed Regioselectivity

Polarity reversal ("umpolung") of a functional group can override its inherent reactivity and lead to distinct bond-forming modes. Herein we describe a rarely studied cycloaddition between nitrile oxides and electron-rich alkynes with reversed regioselect

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

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.

Construction of spiro-1,2,4-oxadiazoline-fused matrine-type alkaloids as pesticidal agents

In order to increase the agricultural properties of matrine, a series of novel matrine-type alkaloids containing spiro-1,2,4-oxadiazoline fragment at the C-15 position were prepared. Eight target molecules were elucidated by X-ray single-crystal diffracti