5470-95-1

Basic information

• Product Name: 2,3-DIMETHOXYBENZALDOXIME
• Synonyms: 2,3-DIMETHOXYBENZALDEHYDE OXIME;2,3-DIMETHOXYBENZALDOXIME;o-veratraldehyde,oxime;Nsc27024;2,3-Dimethoxy-benzaldehyd-oxim
• CAS NO: 5470-95-1
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.19
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 5470-95-1.mol

Chemical Properties

• Melting Point: 98-100°C
• Boiling Point: 293.1°Cat760mmHg
• Flash Point: 131.1°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.000802mmHg at 25°C
• Refractive Index: 1.501
• BRN: 1953084
• CAS DataBase Reference: 2,3-DIMETHOXYBENZALDOXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHOXYBENZALDOXIME(5470-95-1)
• EPA Substance Registry System: 2,3-DIMETHOXYBENZALDOXIME(5470-95-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• RTECS: YX5089710
• Hazardous Substances Data: 5470-95-1(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
2,3-Dimethoxybenzaldoxime is used as a chemical compound for conducting various chemical reactions and experiments. Its unique structure and properties make it a valuable resource in the field of organic chemistry.
Used in Chemical Synthesis:
2,3-Dimethoxybenzaldoxime is used as an intermediate or reactant in the synthesis of other organic compounds. Its versatility in chemical reactions allows for the creation of a wide range of products.
Used in Pharmaceutical Development:
2,3-Dimethoxybenzaldoxime is used as a potential candidate in the development of new pharmaceuticals. Its chemical properties may contribute to the creation of novel drug molecules with therapeutic applications.
Used in Material Science:
2,3-Dimethoxybenzaldoxime is used as a component in the development of new materials with specific properties, such as improved stability or reactivity. Its incorporation into materials can lead to advancements in various industries.
Safety Precautions:
As with many chemicals, appropriate caution must be exercised in handling or using 2,3-Dimethoxybenzaldoxime, as it may act as a skin or eye irritant and could have potential harmful effects if swallowed or inhaled. Proper safety measures, such as wearing protective gear and working in a controlled environment, should be taken to minimize risks.

InChI:InChI=1/C9H11NO3/c1-12-8-5-3-4-7(6-10-11)9(8)13-2/h3-6,11H,1-2H3/b10-6+

Upstream product

• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 868775-52-4 C-(2,3-dimethoxyphenyl)-N-benzyl-nitrone 
• 128349-14-4 Benzyl-(2,3-dimethoxy-benzyl)-amine 

Downstream Products

• 5653-62-3 2,3-dimethoxybenzonitrile 
• 4393-09-3 2,3-dimethoxybenzyl amine 
• 1421869-65-9 C₂₇H₃₃FN₄O₃*ClH 
• 1421869-71-7 C₂₇H₃₃ClN₄O₃*ClH 
• 1421869-77-3 C₂₇H₃₃ClN₄O₃*ClH 
• 1421869-83-1 C₂₈H₃₆N₄O₄*ClH 
• 1421869-89-7 C₂₇H₃₃FN₄O₃*ClH 
• 1421869-95-5 C₃₄H₃₈F₂N₄O₃*ClH 
• 1421870-01-0 C₂₉H₃₈N₄O₃*ClH 
• 1421869-59-1 C₂₇H₃₄N₄O₃*ClH 
• 1421870-07-6 C₂₇H₃₃ClN₄O₃*ClH 
• 26994-71-8 2,3-dimethoxy-benzaldehyde (E)-O-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yl)-oxime 
• 56221-31-9 2,3-dimethoxy-benzylamine; hydrochloride 
• 1111736-11-8 2,3-dimethoxyphenylhydroximoyl chloride 

Relevant articles and documents

1,3-dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene-PTAD and biological activities of adducts formed selectively

After known adduct (4) was synthesized by cycloaddition reaction of cyclopentadiene with 4-phenyl-1,2,4-triazoline-3,5-dione, seven new isoxazoline derivatives were synthesized from reactions of 4 with corresponding oximes prepared from benzaldehyde derivatives in the existence of the aqueous NaOCl in CH2Cl2 at 0°C—RT via nitrile oxides. Four new pyrazoline derivatives were also synthesized from reactions of 4 with corresponding prepared reagents via nitrile imines. Selectively, each of all isoxazole and pyrazoline derivatives was synthesized by 1,3-dipolar cycloaddition reactions of compound 4 with the corresponding reagents. Based on the results of their biological activity analyses, Ki values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glucosidase (α-Gly) enzymes were obtained in this range 32.15 ± 5.73–107.44 ± 19.52 22.57 ± 4.30–186.07 ± 23.51, and 69.08 ± 8.54–528.07 ± 38.46 nM, respectively. Besides that, these compounds were subjected to molecular docking to describe the interaction against AChE, BChE, and α-Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.

AN IMPROVED PROCESS FOR PREPARATION OF PURE ALDOXIME

The present invention relates to an improved process for preparing aldoximes of formula (I) with high purity and high yield. The improved process for preparing aldoxime is fast, simple, highly efficient, and reproducible. The improved process for the preparation of aldoxime, which is synthesized in the higher yield under oximation reaction of aldehyde with hydroxylamine hydrochloride merely in aqueous medium using of in situ heat generation.

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.

Facile synthesis and docking studies of 7-hydroxyflavanone isoxazoles and acrylates as potential anti-microbial agents

The present study is aimed to synthesize the novel 7-hydroxyflavanone derived compounds and to assess their biological activity. Two series of compounds such as 2-phenyl-7-((3-phenylisoxazol-5-yl)methoxy)chroman-4-ones (6a–h) and 4-oxo-2-phenylchroman-7-yl acrylates (8a–k) were synthesized from 7-hydroxyflavanone. All the compounds were subjected to anti-microbial activity and molecular docking studies. The results showed that the compounds 6e, 6g–h, 8h–i and 8k were exhibited most potent anti-microbial activity when compared with the standard drugs. Further, the docking studies revealed that the compounds 6a and 8h have the highest binding affinity score of sterol 14-α demethylase and DNA gyrase B respectively. This is the first report assigning unique synthesis of 7-hydroxyflavanone derivatives and their anti-microbial activity proved with in silico studies. Furthermore, the present study is useful for constructive research to synthesize novel compounds along with their biological activity. [Figure not available: see fulltext.].

Synthesis and cytotoxic evaluation of undecenoic acid-based oxime esters

A series of undecenoic acid-based aldoxime esters have been synthesized using various substituted benzaldehydes and undecenoic acid. These oxime esters have been evaluated for their cytotoxic activities against HeLa, B16-F10, SKOV3, MCF7 and CHO-K1 normal cell line using MTT assay. Most of the synthesized compounds exhibit cytotoxicity. Particularly, 2,3-dimethoxy (IC50 value 12.48μM) and 3-methoxy (IC50 value 13.58μM) derivatives exhibit promising activities against SKOV3 cell lines. All the synthesized compounds are non-toxic towards the Chinese hamster ovary (CHO-K1) normal cell line.

Ruthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors

An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields. An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields.

Sodium nitrite-catalyzed aerobic oxidative Csp2-Csp3 coupling: Direct construction of the 4-aryldihydroisoquinolinone moiety

A bioinspired approach for the construction of the 4- aryldihydroisoquinolinone moiety via direct oxidative Csp2-Csp 3 coupling has been developed, which uses inexpensive sodium nitrite as catalyst and environmentally benign oxygen in the air as terminal oxidant.

Biologically active hydroxymoyl chlorides as antifungal agents

Several oximes and oxime ethers have been developed as antimicrobial agents. A series of chlorooximes (hydroximoyl chlorides) have been synthesized and tested for antifungal activity under in-vitro conditions against Candida albicans, Candida parapsilosis, Candida glabrata, Candida krusei, Aspergillus fumigatus, Aspergilhis flaviis and Aspergillus niger. The derived antifungal activity has been compared with the corresponding oximes. The results show that most of the chlorooximes exhibit potent antifungal activity with anti-isomers showing better activity. It is observed that most of the chlorooximes show interesting antifungal activity (MICs ≤ 32 μg/mL) compared to oximes. Compound 3q (2,3-dimethoxy phenyl hydroxymoyl chloride) is the most active compound. This compound is active against all the Candida species (MIC 0.5 μg/mL) as well as filamentous fungi with MIC range of 2-4 μg/mL. This series of compounds are fungicidal in nature as evident from the MFC results.

One-pot synthesis and hydroxylaminolysis of asymmetrical acyclic nitrones

Aromatic aldehydes 1 were reductively aminated to the corresponding secondary amines 2 using NaBH4 in methanol in good yields. Amines 2 were oxidized with H2O2-WO42- regioselectively to nitrones 3, the structures of which were easily determined by reacting them with hydroxylamine hydrochloride as well as by spectral means. The products of hydroxylaminolysis in ether proved to be the corresponding benzaldehyde oximes 4 and benzyl or methyl hydroxylamine hydrochlorides 5. Copyright Taylor & Francis, Inc.