19463-48-0

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLOROVANILLIN is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
5-CHLOROVANILLIN serves as a key intermediate in the chemical synthesis of various organic compounds, including those with potential applications in the fragrance, flavor, and agrochemical industries. Its reactivity and functional group compatibility make it a valuable component in the synthesis of complex molecules.
Used in Oxidation Reactions:
5-CHLOROVANILLIN is used as a substrate in oxidation reactions catalyzed by enzymes such as laccase. This application is particularly relevant in the field of biotechnology, where enzymes are employed to catalyze specific reactions with high selectivity and efficiency. The product of this reaction, hydroxymethine quinone, can be further utilized in various chemical processes.

InChI:InChI=1/C8H7ClO3/c1-12-7-3-5(4-10)2-6(9)8(7)11/h2-4,11H,1H3

Upstream product

• 507-40-4 tert-butylhypochlorite 
• 121-33-5 vanillin 
• 67-66-3 chloroform 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 20624-92-4 3-chloro-4-hydroxy-5-methoxy-benzyl alcohol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 7782-50-5 chlorine 
• 18268-80-9 2-chloro-6-methoxy-4-methylphenol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 18268-68-3 5-chloroveratraldehyde 
• 182345-46-6 5,5-Dimethyl-2-(4-hydroxy-3-methoxyphenyl)-1,3-dioxane 
• 302321-78-4 4-(5,5-dimethyl-[1,3]dioxan-2-yl)-6,6-dimethoxy-cyclohexa-2,4-dienone 

Downstream Products

• 20624-92-4 3-chloro-4-hydroxy-5-methoxy-benzyl alcohol 
• 5438-40-4 5-CFA 
• 62936-23-6 3-chloro-4-hydroxy-5-methoxybenzoic acid 
• 54490-80-1 2-chloro-6-methoxy-p-benzoquinone 
• 179795-11-0 2-chloro-6-methoxy-hydroquinone 
• 37687-67-5 3-chloro-5-(methyloxy)-4-[(phenylmethyl)oxy]benzaldehyde 
• 18268-68-3 5-chloroveratraldehyde 

Relevant academic research and scientific papers

Efficient halogenation synthesis method of aryl halide

The invention discloses an efficient halogenation synthesis method of aryl halide. The method comprises the following step: in the presence of a catalyst (sulfoxide or oxynitride), a halogenation reagent and a solvent, carrying out a halogenation reaction on an aromatic ring compound to obtain the aryl halide. According to the present invention, in the presence of a catalyst (sulfoxide or nitrogenoxide), a halogenation reagent and a solvent, the aromatic ring is subjected to an efficient halogenation reaction, such that the very useful aryl halide can be obtained with high activity and high selectivity; and by adopting the method disclosed by the invention, aryl halides can be efficiently synthesized, and the method has a wide application prospect in actual production.

IMIDAXOPYROLONE COMPOUND AND APPLICATION THEREOF

Disclosed is a novel class of MDM2-p53 inhibitor compounds having an imidaxopyrolone structure, and specifically disclosed are compounds represented by formulas (I-1) and (I-2) and pharmaceutically acceptable salts thereof. (I-1), (I-2)

Halogenated trimethoprim derivatives as multidrug-resistant Staphylococcus aureus therapeutics

Incorporation of halogen atoms to drug molecule has been shown to improve its properties such as enhanced in membrane permeability and increased hydrophobic interactions to its target. To investigate the effect of halogen substitutions on the antibacterial activity of trimethoprim (TMP), we synthesized a series of halogen substituted TMP and tested for their antibacterial activities against global predominant methicillin resistant Staphylococcus aureus (MRSA) strains. Structure-activity relationship analysis suggested a trend in potency that correlated with the ability of the halogen atom to facilitate in hydrophobic interaction to saDHFR. The most potent derivative, iodinated trimethoprim (TMP-I), inhibited pathogenic bacterial growth with MIC as low as 1.25 μg/mL while the clinically used TMP derivative, diaveridine, showed resistance. Similar to TMP, synergistic studies indicated that TMP-I functioned synergistically with sulfamethoxazole. The simplicity in the synthesis from an inexpensive starting material, vanillin, highlighted the potential of TMP-I as antibacterial agent for MRSA infections.

Unanticipated participation of HCl in nucleophilic chlorination reaction: Expedient route to meta chlorophenols

o-Quinone monoketals participated in a 1,4-addition reaction with HCl furnishing m-chlorophenols in high yields. Several readily available o-quinone monoketals were selected to display the generality of this serendipitous and unprecedented reaction and the results are presented herein.

Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines

This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.

Chemoselective zinc/HCl reduction of halogenated β-nitrostyrenes: Synthesis of halogenated dopamine analogues

A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 °C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students

We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.

Efficient Co(OAc)2-catalyzed aerobic oxidation of EWG-substituted 4-cresols to access 4-hydroxybenzaldehydes

We reported an efficient ligand-free Co(OAc)2·4H 2O/NaOH/O2/ethylene glycol reaction system that enables selective aerobic oxidation of a wide range of substrates covering 2,6-di-EWG-, 2,3,6-tri-EWG-, 2-EWG-, and 2-EWG-6-EDG-substituted 4-cresols into the corresponding 4-hydroxybenzaldehydes. Based on the experimental investigations and well-defined p-benzoquinone methides, a plausible reaction mechanism was proposed. Considering the simplicity of the procedure and importance of the products, the methodology was expected to become a favorable and practical tool in related benzylic C(sp3)-H functionalization chemistry.

The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands

A series of carbonate analogues of 5′-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with Ki(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism.

SUBSTITUTED PYRAZOLE-CONTAINING COMPOUNDS AND THEIR USE AS PESTICIDES

The present invention relates to substituted pyrazole-containingcompounds of formula (I), and the stereoisomers and salts thereof, wherein the substituents are as defined in the description. The present invention further relates to a method for combating or controlling invertebrate pests, to a method for protecting plant propagation material and/or the plants which grow therefrom, to plant propagation material comprising at least one compound according to the present invention, to a method for treating or protecting an animal from infestation or infection by parasites, to a process for the preparation of a composition for treating infested or infected animals and/or for protecting animals against infestation or infection by parasites, and to a compound according to the invention for use as a medicament.