1927-94-2

Usage

Uses

Used in Organic Synthesis:
3-Chloro-2-hydroxy-benzaldehyde is used as a key intermediate in the synthesis of a wide range of organic compounds. Its unique structure allows for various chemical reactions, such as condensation, substitution, and oxidation, enabling the formation of complex molecules with diverse applications across different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-chloro-2-hydroxy-benzaldehyde is utilized as a building block for the development of new drugs and active pharmaceutical ingredients. Its ability to form various chemical bonds makes it suitable for the creation of novel drug candidates with potential therapeutic properties.
Used in Agrochemical Industry:
3-Chloro-2-hydroxy-benzaldehyde also finds application in the agrochemical industry, where it serves as a precursor for the synthesis of pesticides, herbicides, and other crop protection agents. Its reactivity allows for the development of effective and targeted chemical solutions to protect crops from pests and diseases.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 3-chloro-2-hydroxy-benzaldehyde is employed as a starting material for the production of various dyes and pigments. Its chemical properties enable the creation of a wide array of colors and shades, catering to the diverse needs of different applications, such as textiles, plastics, and printing inks.
Used in Flavor and Fragrance Industry:
3-Chloro-2-hydroxy-benzaldehyde is also used in the flavor and fragrance industry as a raw material for the synthesis of various aroma chemicals. Its unique chemical structure allows for the development of distinct scents and flavors, contributing to the creation of new and innovative products in the market.

InChI:InChI=1/C7H5ClO2/c8-6-3-1-2-5(4-9)7(6)10/h1-4,10H

Upstream product

• 302-17-0 chloral hydrate 
• 95-57-8 2-monochlorophenol 
• 22471-02-9 2-chloro-6-(hydroxymethyl)phenol 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 100-97-0 hexamethylenetetramine 
• 1829-32-9 3-Chloro-2-hydroxybenzoic acid 
• 76-03-9 trichloroacetic acid 
• 67-66-3 chloroform 
• 50-00-0 formaldehyd 
• 55359-66-5 3-Chlor-2-methoxymethoxy-benzaldehyd 
• 56-81-5 glycerol 
• 75-47-8 iodoform 
• 75-25-2 Bromoform 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 732-60-5 isonicotinic acid-(3-chloro-2-hydroxy-benzylidenehydrazide) 
• 65685-54-3 7-chloro-benzo[d]isoxazole 
• 64037-11-2 7-chlorobenzo[d]oxazol-2-amine 
• 53844-96-5 3-chloro-5-nitrosalicylaldehyde 
• 67810-64-4 3-chloro-2-hydroxy-benzaldehyde-semicarbazone 
• 65685-40-7 3-chlorosalicylaldoximine 
• 63558-84-9 7-chlorobenzofuran-2-carboxylic acid 
• 10319-02-5 N,N'-bis-(3-chloro-2-hydroxy-benzyliden)-ethylenediamine 
• 1774-51-2 2,2'-Dihydroxy-5'-brom-3-chlor-chalkon 
• 1829-32-9 3-Chloro-2-hydroxybenzoic acid 
• 80352-52-9 2-(benzyloxy)-3-chlorobenzaldehyde 
• 15934-92-6 2,4'-Dihydroxy-3,5'-dichlor-chalkon 
• 24581-95-1 6-Chlor-2-formyl-phenoxyessigsaeure-methylester 
• 25458-14-4 2-Chloro-6-{[(E)-2-hydroxy-1,1-dimethyl-ethylimino]-methyl}-phenol 

Relevant academic research and scientific papers

Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines

Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.

Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines

A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.

Cytotoxicity of new pyridazin-3(2H)-one derivatives orchestrating oxidative stress in human triple-negative breast cancer (MDA-MB-468)

Triple-negative breast cancer (TNBC) is a complex and aggressive subtype of breast cancer characterized by high morbidity and mortality. In the absence of targeted therapy, only chemotherapy is available in this case of cancer. The current study investigated the antitumor effect of new pyridazin-3(2H)-one derivatives on the human TNBC cell line, MD-MB-468. The in vitro cytotoxic activities were investigated using the tetrazolium-based MTT assay. Lipid peroxidation, H2O2 content, and the specific activities of antioxidant enzymes were also determined. Two molecules, 6f and 7h, were found to be selectively highly active against tumor cells with IC50 values of 3.12 and 4.9 μM, respectively. Furthermore, cells exposed to 6f showed a significant increase in H2O2 and lipid peroxidation levels, accompanied by a decrease in the enzyme activities of glutathione reductase (GR) and thioredoxin reductase (TrxR). The cytotoxicity of the compound 6f may improve the therapeutic efficacy of the current treatment for TNBC via the inhibition of GR and TrxR activities.

Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction

Chiral β-amino alcohol ligands were found effective for the copper(ii)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl β-amino alcohols could be conveniently prepared in short steps.

Phosphine-Catalyzed [4 + 2] Annulation of Allenoate with Sulfamate-Derived Cyclic Imines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate

A phosphine-catalyzed [4 + 2] cycloaddition of cyclic α-substituted allenoates with sulfamate-derived cyclic imines has been reported. Using dibenzylphenylphosphine as the nucleophilic catalyst, the reaction worked efficiently to yield various fused multicyclic heterocyclic compounds in high yields with excellent diastereoselectivities. It undergoes a new reaction mode involving γ′-carbon of α-substituted allenoate.

Transition Metal Ions as Efficient Catalysts for Vilsmeier-Haack Formylation of Hydrocarbons with Reagents: Kinetics and Mechanism

The Vilsmeier-Haack formylation reactions with hydrocarbons are sluggish in acetonitrile medium. The VH reactions follows second-order kinetics and affords formyl derivatives under kinetic conditions that are also irrespective of the nature of the oxychloride (POCl3 or SOCl2) used for the preparation of VH reagent along with DMF. However, the reactions undergo significant rate accelerations in the presence of transition metal ions such as Cu(II), Ni(II), Co(II) and Cd(II). Transition metal ion catalyzed VH formylation is explained through the formation of a mixed ligand complex of the [M(II)S(VHR)] type prior to the rate determining rearrangement step, before yielding formyl derivatives of hydrocarbons.

Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction

A copper-mediated Duff reaction for ortho-selective formylation of phenols has been developed. In the presence of copper species, significant improvements of yield and ortho-selectivity of the Duff formylation were achieved, which provides an easy access to salicylaldehydes from phenols.

SULFAMATE DERIVATIVE COMPOUNDS FOR USE IN TREATING OR ALLEVIATING PAIN

The present invention relates to sulfamate derivative compounds and a composition for treating and/or alleviating pain containing the sulfamate derivative compounds or a pharmaceutically acceptable salt thereof as an active ingredient. More specifically,

Facile one-pot transformation of phenols into o-cyanophenols

The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.

2,2,6,6-Tetramethylpiperidine-catalyzed, ortho-selective chlorination of phenols by sulfuryl chloride

2,2,6,6-Tetramethylpiperidine (TMP)-catalyzed (1- 10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2'- hydroxyacetophenone. Notably, ortho selectivity increases with the reaction temperature. On the other hand, tetraalkylammonium chloride-catalyzed chlorinations are moderately para selective.