1076-95-5

Basic information

• Product Name: 2-(4-methoxyphenyl)-2-oxoacetaldehyde
• Synonyms: 2-(4-methoxyphenyl)-2-oxoacetaldehyde;4-methoxyphenylglyoxal;1-(4-Methoxyphenyl)-1,2-ethanedione;1-(4-Methoxyphenyl)ethanedione;1-(4-Methoxyphenyl)glyoxal;2-Oxo-2-(4-methoxyphenyl)ethanal;4-Methoxy-α-oxobenzeneacetaldehyde;α-Oxo-4-methoxybenzeneacetaldehyde
• CAS NO: 1076-95-5
• Molecular Formula: C₉H₈O₃
• Molecular Weight: 164.15802
• EINECS: 214-067-0
• Mol File: 1076-95-5.mol
• Article Data: 85

Chemical Properties

• Boiling Point: 265.3°Cat760mmHg
• Flash Point: 114.1°C
• Appearance: /
• Density: 1.153g/cm³
• Vapor Pressure: 0.00921mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 2-(4-methoxyphenyl)-2-oxoacetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methoxyphenyl)-2-oxoacetaldehyde(1076-95-5)
• EPA Substance Registry System: 2-(4-methoxyphenyl)-2-oxoacetaldehyde(1076-95-5)

Safety Data

• Hazardous Substances Data: 1076-95-5(Hazardous Substances Data)

Usage

Description

2-(4-methoxyphenyl)-2-oxoacetaldehyde is a chemical compound belonging to the class of organic compounds known as benzaldehydes. It is characterized by its phenyl ring with a methoxy group at the 4-position and an aldehyde group attached to the carbon atom adjacent to the phenyl ring, leading to a carbonyl group. This distinctive benzaldehyde contains a benzene ring with at least one carbon atom substituted with a formyl group and a methyl group bound to an oxygen atom. However, there is limited data on its specific properties and applications, indicating that it may not be widely used or studied in the scientific community.

Uses

Due to the limited information provided on the specific applications of 2-(4-methoxyphenyl)-2-oxoacetaldehyde, it is challenging to list its uses in various industries. However, as a benzaldehyde derivative, it may potentially be used in the following areas:
Used in Pharmaceutical Industry:
2-(4-methoxyphenyl)-2-oxoacetaldehyde could be used as an intermediate in the synthesis of pharmaceutical compounds, given its unique structure and functional groups.
Used in Flavor and Fragrance Industry:
As a derivative of benzaldehyde, it may be used as a component in the creation of various fragrances and flavorings, taking advantage of its aromatic properties.
Used in Chemical Research:
2-(4-methoxyphenyl)-2-oxoacetaldehyde could be employed as a research compound in academic or industrial laboratories to study its chemical properties, reactivity, and potential applications in various chemical reactions.

InChI:InChI=1/C9H8O3/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-6H,1H3

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 67-66-3 chloroform 
• 6327-79-3 1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione 
• 2196-99-8 2-chloro-1-(4-methoxyphenyl)ethanone 
• 7446-08-4 selenium(IV) oxide 
• 66702-78-1 1-(4-Methoxy-phenyl)-2-nitrooxy-ethanone 
• 80336-72-7 2-iodo-1-(4-methoxyphenyl)ethanone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 1195512-57-2 2-(4-methoxyphenyl)-2-oxoethane-1,1-diyl diacetate 
• 1262623-27-7 2-(2-(4-methoxyphenyl)-2-oxoethoxy)isoindoline-1,3-dione 
• 1374568-26-9 2,2-diiodo-1-(4-methoxyphenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 265999-47-1 α-(diiodomethyl)-4-methoxybenzenemethanol 
• 637-69-4 4-Methoxystyrene 

Downstream Products

• 856348-33-9 3-(4-methoxy-phenyl)-hexane-3,4-diol 
• 51758-56-6 (4-methoxy-phenyl)-glyoxal-(2,4-dinitro-phenylhydrazone) 
• 13664-91-0 (4-methoxy-phenyl)-glyoxal-bis-(2,4-dinitro-phenylhydrazone) 
• 25561-40-4 1-(4-methoxy-phenyl)-2-morpholin-4-ylimino-ethanone 
• 22283-99-4 [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-2,3-dihydro-thiazol-2-yl]-(4-methoxy-phenyl)-ethanedione 
• 67200-30-0 5-(4-methoxyphenyl)furazano[3,4-b]pyrazine 
• 22716-41-2 p-Anisoylformoin 
• 123488-68-6 2-(4-Methoxy-phenyl)-7H-imidazo[1,2-a]pyrazin-3-one 
• 70504-14-2 7-(p-methoxyphenyl)-4(3H)-pteridinone 
• 2166-90-7 1-Methoxy-4-(α-hydroxy-α-benzamino-acetyl)-benzol 
• 2166-97-4 1-Methoxy-4-<α-hydroxy-α-(p-toluolsulfonylamino)-acetyl>-benzol 
• 2187-24-8 1-Methoxy-4-(α-hydroxy-α-thioacetamino-acetyl)-benzol 
• 1948-98-7 1-Methoxy-4-(α-hydroxy-α-phenylacetamino-acetyl)-benzol 
• 13305-14-1 methyl 2-hydroxy-2-(4-methoxyphenyl)acetate 

Relevant articles and documents

Characterization and Synthesis of Eudistidine C, a Bioactive Marine Alkaloid with an Intriguing Molecular Scaffold

An extract of Eudistoma sp. provided eudistidine C (1), a heterocyclic alkaloid with a novel molecular framework. Eudistidine C (1) is a racemic natural product composed of a tetracyclic core structure further elaborated with a p-methoxyphenyl group and a phenol-substituted aminoimidazole moiety. This compound presented significant structure elucidation challenges due to the large number of heteroatoms and fully substituted carbons. These issues were mitigated by application of a new NMR pulse sequence (LR-HSQMBC) optimized to detect four- and five-bond heteronuclear correlations and the use of computer-assisted structure elucidation software. Synthesis of eudistidine C (1) was accomplished in high yield by treating eudistidine A (2) with 4(2-amino-1H-imidazol-5-yl)phenol (4) in DMSO. Synthesis of eudistidine C (1) confirmed the proposed structure and provided material for further biological characterization. Treatment of 2 with various nitrogen heterocycles and electron-rich arenes provided a series of analogues (5-10) of eudistidine C. Chiral-phase HPLC resolution of epimeric eudistidine C provided (+)-(R)-eudistidine C (1a) and (-)-(S)-eudistidine C (1b). The absolute configuration of these enantiomers was assigned by ECD analysis. (-)-(S)-Eudistidine C (1b) modestly inhibited interaction between the protein binding domains of HIF-1α and p300. Compounds 1, 2, and 6-10 exhibited significant antimalarial activity against Plasmodium falciparum.

Design and synthesis of coumarin-glyoxal hybrids for spermicidal and antimicrobial actions: A dual approach to contraception

Today there is an urgent need for safe and effective dual-purpose contraceptive agents, which can simultaneously prevent unintended pregnancies and sexually transmitted infections (STI). There are several naturally occurring antimicrobial and antibiotic drugs (novobiocin, coumermycin and chlorobiocin) reported in the literature, which are based on 4-hydroxy coumarins as the active pharmacophore. Based on these interesting reports, we designed and synthesized a library of new 4-hydroxy coumarin derivatives and evaluated them for spermicidal activity. Among the tested compounds, two compounds (2a and 2d) displayed better activity (greater than 95% sperm immobilization at 0.5 mM concentration) than the positive control nonoxynol-9 (N-9). Furthermore, all the compounds were screened for antimicrobial activity against different strains of Trichomonas vaginalis and two compounds (2c and 2h) exhibited potent activity as compared to the reference drug metronidazole. The cytotoxicity assay showed that most of these compounds were safer than the N-9 against the human cervical HeLa cell line and normal vaginal flora Lactobacillus jensenii strains. The studies have demonstrated that compound (2a) is a potential lead to develop a dually active vaginal contraceptive.

Synthesis of α-keto aldehydes via selective Cu(i)-catalyzed oxidation of α-hydroxy ketones

An efficient approach to synthesize α-keto aldehydes was established through selective oxidation of α-hydroxy ketones catalyzed by Cu(i) using oxygen as oxidant. A wide array of α-keto aldehydes was prepared with isolated yields of up to 87%. The potential utilization of this reaction was evaluated by gram-scale reactions and synthetic applications.

A novel class for carbonic anhydrases inhibitors and evaluation of their non-zinc binding

In this study, 23 different imidazole derivatives were synthesized, and the inhibitory properties of these derivatives against carbonic anhydrase I and II isoenzymes were investigated for the first time. The inhibition concentrations of the imidazole derivatives were found to be in the range of 2.89–115.5 nM. Docking studies examined the binding properties of the imidazole derivatives, and the structure–activity relationship is discussed. Theoretical calculations showed that the binding mode of the imidazole ring was non-zinc binding.

Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides

Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.