34231-78-2

Usage

Uses

Used in Organic Synthesis:
3-Acetoxybenzaldehyde is used as an important intermediate in organic synthesis for the production of various compounds. Its reactivity and functional groups make it a valuable precursor for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and dyes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-acetoxybenzaldehyde is utilized as a key intermediate for the synthesis of various drugs and drug candidates. Its ability to undergo a range of chemical reactions, such as nucleophilic addition, electrophilic substitution, and reduction, allows for the creation of diverse pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
3-Acetoxybenzaldehyde also finds application in the agrochemical industry, where it serves as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its functional groups can be modified to create compounds with specific biological activities, making it a valuable asset in the development of new agrochemical products.
Used in Dye Industry:
In the dye industry, 3-acetoxybenzaldehyde is employed as an intermediate for the production of various dyes and pigments. Its aromatic structure and functional groups can be modified to create a wide range of colored compounds, which are used in various applications, such as textiles, plastics, and printing inks.

Upstream product

• 108-24-7 acetic anhydride 
• 100-83-4 meta-hydroxybenzaldehyde 
• 60-29-7 diethyl ether 
• 6304-89-8 3-acetoxybenzoic acid 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 111342-08-6 3-(dibromomethyl)phenyl acetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 78523-29-2 1-hydroxy-1-(3-hydroxyphenyl)propan-2-one 
• 114354-08-4 3-acetoxy-benzaldehyde-selenosemicarbazone 
• 64781-20-0 (3-acetoxy-benzylidene)-malononitrile 
• 18238-93-2 3-Acetoxy-α-fluor-zimtsaeure-ethylester 
• 18114-52-8 4-(3-acetoxy-benzylidene)-2-(4-acetylamino-phenyl)-4H-oxazol-5-one 
• 27542-84-3 (2E)-3-(3-acetyloxyphenyl)acrylic acid 
• 95392-02-2 Acetic acid 3-(cyano-trimethylsilanyloxy-methyl)-phenyl ester 
• 78187-95-8 3-Acetoxybenzaldehydcyanhydrin 
• 78957-20-7 3-(hydroxymethyl)phenyl acetate 
• 78515-19-2 Acetic acid 3-[(E)-2-(3-acetoxy-phenyl)-vinyl]-phenyl ester 
• 25673-60-3 trans-3-(3-acetoxybenzylidene)-3,4-dihydro-4-methyl-1H-1,4-benzodiazepine-2,5-dione 
• 25673-61-4 1-acetyl-trans-3-(3-acetoxybenzylidene)-3,4-dihydro-4-methyl-1H-1,4-benzodiazepine-2,5-dione 
• 116324-76-6 4-(3-Acetoxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester 
• 24393-13-3 2'-(3-hydroxyphenyl)-[1',3']-dioxane 

Relevant academic research and scientific papers

Development of antimicrobial laser-induced photodynamic therapy based on ethylcellulose/chitosan nanocomposite with 5,10,15,20-tetrakis(M-hydroxyphenyl)porphyrin

The development of new antimicrobial strategies that act more efficiently than traditional antibiotics is becoming a necessity to combat multidrug-resistant pathogens. Here we report the effi-cacy of laser-light-irradiated 5,10,15,20-tetrakis(m-hydroxyphenyl)porphyrin (mTHPP) loaded onto an ethylcellulose (EC)/chitosan (Chs) nanocomposite in eradicating multi-drug resistant Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans. Surface loading of the ethylcelllose/chitosan composite with mTHPP was carried out and the resulting nanocomposite was fully characterized. The results indicate that the prepared nanocomposite incorporates mTHPP inside, and that the composite acquired an overall positive charge. The incorporation of mTHPP into the nanocomposite enhanced the photo-and thermal stability. Different laser wavelengths (458; 476; 488; 515; 635 nm), powers (5–70 mW), and exposure times (15–45 min) were investigated in the antimicrobial pho-todynamic therapy (aPDT) experiments, with the best inhibition observed using 635 nm with the mTHPP EC/Chs nanocomposite for C. albicans (59 ± 0.21%), P. aeruginosa (71.7 ± 1.72%), and S. aureus (74.2 ± 1.26%) with illumination of only 15 min. Utilization of higher doses (70 mW) for longer periods achieved more eradication of microbial growth.

3-/4-ester substituted benzaldehyde thiosemicarbazone derivatives as well as preparation and application thereof

The invention belongs to the technical field of tyrosinase inhibitors, and discloses 3-/4-ester substituted benzaldehyde thiosemicarbazone derivatives as well as preparation and an application thereof. The 3-/4-ester substituted benzaldehyde thiosemicarbazone derivatives have a structural formula represented by a formula I shown in the description, wherein RCOO- is used as a 3-position substituentor 4-position substituent, and R is alkyl, phenyl or benzyl. The 3-/4-ester substituted benzaldehyde thiosemicarbazide derivatives provided by the invention are used as the tyrosinase inhibitors, andused for preparation of a medicine for treating Parkinson syndrome and an anti-melanoma medicine, and preparation of whitening cosmetics, biological insecticides and food preservatives. The 3-/4-ester substituted benzaldehyde thiosemicarbazone derivatives provided by the invention are extremely simply synthesized, and can be obtained only through a simple esterification reaction and a Schiff basereaction; and meanwhile the 3-/4-ester substituted benzaldehyde thiosemicarbazone derivatives provided by the invention have better activity, and have strong inhibitory activity against tyrosinase.

Synthesis of functionally substituted benzaldehydes

A new method of synthesis of functionally substituted benzaldehydes by catalytic debromometoxylation of dibromomethylarenes with benzaldehyde dimethyl acetal has been suggested. Anhydrous zinc chloride has been used as a catalyst. Being soft Lewis acid, it formed no strong complex with aldehyde group and other functional groups. The initial acetal has been readily recovered by the treatment of benzaldehyde isolated from the reaction mixture with trimethyl orthoformate.

Chemoselective reduction of the carbonyl functionality through hydrosilylation: Integrating click catalysis with hydrosilylation in one pot

Herein we report the chemoselective reduction of the carbonyl functionality via hydrosilylation using a copper(I) catalyst bearing the abnormal N-heterocyclic carbene 1 with low (0.25 mol %) catalyst loading at ambient temperature in excellent yield within a very short reaction time. The hydrosilylation reaction of α,β-unsaturated carbonyl compounds takes place selectively toward 1,2-addition (C=O) to yield the corresponding allyl alcohols in good yields. Moreover, when two reducible functional groups such as imine and ketone groups are present in the same molecule, this catalyst selectively reduces the ketone functionality. Further, 1 was used in a consecutive fashion by combining the Huisgen cycloaddition and hydrosilylation reactions in one pot, yielding a range of functionalized triazole substituted alcohols in excellent yields.

Iron (III) phosphate as a green and reusable catalyst promoted chemo selective acetylation of alcohols and phenols with acetic anhydride under solvent free conditions at room temperature

Iron (III) phosphate was employed as an efficient catalyst for the chemo selective acetylation of alcohols and phenols under solvent free condition at room temperature and with high yields. Iron (III) phosphate is also a potential green catalyst due to solid intrinsically, reusable and with high catalytic activity.

Chemical insights in the concept of hybrid drugs: The antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin

Hybrid drug 1 (NO-ASA) continues to attract intense research from chemists and biologists alike. It consists of ASA and a -ONO2 group connected through a spacer and is in preclinical development as an antitumor drug. We report that, contrary to current beliefs, neither ASA nor NO contributes to this antitumor effect. Rather, an unsubstituted QM was identified as the sole cytotoxic agent. QM forms from 1 after carboxylic ester hydrolysis and, in accordance with the HSAB theory, selectively reacts with cellular GSH, which in turn triggers cell death. Remarkably, a derivative lacking ASA and the -ONO 2 group is 10 times more effective than 1. Thus, our data provide a conclusive molecular mechanism for the antitumor activity of 1. Equally importantly, we show for the first time that a "presumed invisible" linker in a hybrid drug is not so invisible after all and is in fact solely responsible for the biological effect.

Microwave-assisted NiCl2 promoted acylation of alcohols

A microwave oven acylation of alcohols by carboxylic acid anhydrides has been developed. NiCl2 has been proven an efficient catalyst for the acylation of primary, secondary, and tertiary alcohols and phenols under microwave conditions.

New Pd-catalyzed selective reduction of carboxylic acids to aldehydes.

A catalyst generated in situ from palladium acetate and tricyclohexylphosphine efficiently catalyzes the reduction of carboxylic acids with sodium hypophosphite in the presence of pivalic anhydride to give aldehydes with high selectivity. The low cost and convenient handling of the reagents makes this process a valuable alternative to hydrogenations and metal hydride reductions.

Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

A novel synthesis of compounds having the formula: STR1 wherein T is a stabilizing spiro-linked polycycloalkylidene group, R3 is a C1 -C20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula: wherein R1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula: wherein R3 is as defined above, to produce a 1-alkoxy-1-arylmethane phosphonate ester of the formula: STR2 reacting the phosphonate with base to produce a phosphonate-stabilized carbanion, reacting the carbanion with a ketone of the formula: wherein T is as defined above, to produce an enol ether of the formula: STR3 then oxygenating the double bond in the enol ether to give the corresponding 1,2-dioxetane compound.

Cobalt(II)-Catalyzed Reaction of Aldehydes with Acetic Anhydride under an Oxygen Atmosphere: Scope and Mechanism

The reaction of aldehydes with acetic anhydride in the presence of catalytic cobalt(II) chloride under an oxygen atmosphere at ambient temperature is dependent upon the reaction medium.Aliphatic aldehydes react in acetonitrile to give 1,2-diones whereas the aromatic aldehydes are acylated to yield the corresponding acylals.On the other hand, carboxylic acids are obtained from aliphatic and aromatic aldehydes by conducting the reaction in dichloroethane or benzene.Cobalt(II) chloride in acetonitrile catalyzes the conversion of aliphatic aldehydes to the correspondinganhydrides in the absence of acetic anhydride whereas aromatic aldehydes remain largely unaffected under these conditions.A preliminary mechanistic study in three different solvents (i.e. acetonitrile, dichloroethane, and DMF) has revealed that in acetonitrile and in the presence of acetic anhydride, aliphatic aldehydes behave differently than aromatic aldehydes.Some trapping experiments using methyl acrylate and stilbene have been conducted to demonstrate the occurence of an acyl cobalt and peroxyacyl cobalt intermediate during these reactions.