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
• Article Data: 12

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

General Description

2,3-Dimethoxybenzaldoxime is a chemical compound that belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Often used in scientific research, 2,3-Dimethoxybenzaldoxime has a molecular formula of C9H11NO3. It is understood to have applications in multiple fields for performing different reactions. However, 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.

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 
• 116120-17-3 {6-[2-(2,3-Dimethoxy-benzylamino)-ethyl]-benzo[1,3]dioxol-5-yl}-methanol 
• 116120-11-7 N-(2,3-Dimethoxy-benzyl)-2-(6-hydroxymethyl-benzo[1,3]dioxol-5-yl)-acetamide 
• 116120-18-4 N-(2,3-Dimethoxy-benzyl)-2,2,2-trifluoro-N-[2-(6-formyl-benzo[1,3]dioxol-5-yl)-ethyl]-acetamide 
• 116182-61-7 (13R,13aS)-9,10-Dimethoxy-13-p-tolylsulfanyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline 
• 116120-16-2 (13S,13aS)-9,10-Dimethoxy-13-p-tolylsulfanyl-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline 
• 116120-14-0 (R)-6-(2,3-Dimethoxy-benzyl)-5-((R)-toluene-4-sulfinylmethyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 116120-14-0 (S)-6-(2,3-Dimethoxy-benzyl)-5-((R)-toluene-4-sulfinylmethyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 116120-12-8 N-(2,3-Dimethoxy-benzyl)-2,2,2-trifluoro-N-(2-{6-[(Z)-2-((R)-toluene-4-sulfinyl)-vinyl]-benzo[1,3]dioxol-5-yl}-ethyl)-acetamide 
• 116120-12-8 N-(2,3-Dimethoxy-benzyl)-2,2,2-trifluoro-N-(2-{6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-benzo[1,3]dioxol-5-yl}-ethyl)-acetamide 
• 1111736-11-8 2,3-dimethoxyphenylhydroximoyl chloride 
• 1111736-13-0 2,3-dimethoxyphenylhydroximoyl chloride 
• 56221-31-9 2,3-dimethoxy-benzylamine; hydrochloride 
• 861523-11-7 N-(2,3-dimethoxybenzyl)acetamide 

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.

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.

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.