50329-91-4

Basic information

• Product Name: 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE
• Synonyms: 4-CHLORO-3-FORMYLCOUMARIN;4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE;AKOS BB-9945;AURORA KA-4151;TIMTEC-BB SBB003464;4-Chloro-3-formylcoumarin 97%;4-chloro-2-oxochromene-3-carbaldehyde
• CAS NO: 50329-91-4
• Molecular Formula: C₁₀H₅ClO₃
• Molecular Weight: 208.6
• Product Categories: Building Blocks;Coumarins;CoumarinsHeterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 50329-91-4.mol
• Article Data: 53

Chemical Properties

• Melting Point: 126-130 °C(lit.)
• Boiling Point: 374.5 °C at 760 mmHg
• Flash Point: 173.7 °C
• Appearance: /
• Density: 1.47 g/cm³
• Vapor Pressure: 8.34E-06mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE(50329-91-4)
• EPA Substance Registry System: 4-CHLORO-2-OXO-2H-CHROMENE-3-CARBALDEHYDE(50329-91-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 50329-91-4(Hazardous Substances Data)

Usage

Description

4-Chloro-2-oxo-2H-chromene-3-carbaldehyde, also known as 4-chloro-3-formylcoumarin, is a coumarin derivative characterized by its unique chemical structure and properties. It is a compound with a tricyclic structure, featuring a benzene ring fused to a pyran ring, which is further fused to a coumarin moiety. The presence of a chlorine atom at the 4-position and a formyl group at the 3-position provides this molecule with specific reactivity and potential applications in various fields.

Uses

4-Chloro-2-oxo-2H-chromene-3-carbaldehyde is used as a versatile reactant in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries. Its unique structure allows it to participate in a range of chemical reactions, leading to the formation of diverse products with potential applications.
Used in Pharmaceutical Industry:
4-Chloro-2-oxo-2H-chromene-3-carbaldehyde is used as a key intermediate in the synthesis of 2-aryl[1]benzopyrano[4,3-c]pyrazol-4(2H)-ones, which are compounds with potential biological activities. These synthesized compounds may exhibit properties such as anti-inflammatory, analgesic, and anti-cancer effects, making them valuable for the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-chloro-2-oxo-2H-chromene-3-carbaldehyde is used as a starting material for the preparation of biaryl lactones (benzo[c]chromen-6-ones). These compounds are of interest due to their potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Organic Chemistry:
4-Chloro-2-oxo-2H-chromene-3-carbaldehyde is also used in the synthesis of N-monosubstituted 4-amino-3-formylcoumarins, which are important building blocks for the development of novel heterocyclic compounds. These compounds may find applications in various fields, such as pharmaceuticals, dyes, and pigments.
Used in Heterocyclic Chemistry:
This coumarin derivative is employed in the preparation of chromeno[4,3-b]quinolin-6-one, a tricyclic compound with potential applications in the field of heterocyclic chemistry. The unique structure of this compound may lead to the development of new drugs with novel mechanisms of action or the creation of new materials with specific properties.

InChI:InChI=1/C10H5ClO3/c11-9-6-3-1-2-4-8(6)14-10(13)7(9)5-12/h1-5H

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 68-12-2 N,N-dimethyl-formamide 
• 607-71-6 4-methyl-2H-chromen-2-one 
• 35756-54-8 malonic acid monophenyl ester 
• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 
• 2650-14-8 3-bromo-4-hydroxycoumarin 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 154417-83-1 4-(N-allylanilino)-3-formyl-2(2H)-chromenone 
• 154417-78-4 6-(N-allylbenzylamino)-3-formyl[1]benzopyran-2(2H)-one 
• 7348-53-0 9-methoxy-6H-chromeno[4,3-b]quinolin-6-one 
• 136806-23-0 4-(4-Tolylamino)-3-cumarincarbaldehyd 
• 1229011-33-9 (2Z,4Z)-N-(2,3-difluorobenzyl)-8,9-difluoro-5-(2-hydroxyphenyl)-1H-benzo[C]azepine-4-carboxamide 
• 1229011-29-3 (2Z,4Z)-5-(2-hydroxyphenyl)-9-methyl-N-(2-methylbenzyl)-1H-benzo[C]azepine-4-carboxamide 
• 1229011-30-6 (2Z,4Z)-5-(2-hydroxyphenyl)-8-methyl-N-(3-methylbenzyl)-1H-benzo[C]azepine-4-carboxamide 
• 1229011-26-0 (2Z,4Z)-7-chloro-N-(4-chlorobenzyl)-5-(2-hydroxyphenyl)-1H-benzo[C]azepine-4-carboxamide 
• 1229011-25-9 (2Z,4Z)-5-(2-hydroxyphenyl)-7-methoxy-N-(4-methoxybenzyl)-1H-benzo[C]azepine-4-carboxamide 

Relevant articles and documents

Synthesis, antimycobacterial activity and docking study of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives and related hydrazide-hydrazones

A new convenient method for preparation of 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives 5b–g and coumarin containing hydrazide-hydrazone analogues 4a–e was presented. The antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and cytotoxicity against the human embryonic kidney cell line HEK-293 were tested in vitro. All compounds demonstrated significant minimum inhibitory concentrations (MIC) ranging 0.28–1.69?μM, which were comparable to those of isoniazid. The cytotoxicity (IC50?>?200?μM) to the “normal cell” model HEK-293T exhibited by 2-aroyl-[1]benzopyrano[4,3-c]pyrazol-4(1H)-one derivatives 5b–e, was noticeably milder compared to that of their hydrazone analogues 4a–e (IC50 33–403?μM). Molecular docking studies on compounds 4a–e and 5b–g were also carried out to investigate their binding to the 2-trans-enoyl-ACP reductase (InhA) enzyme involved in M. tuberculosis cell wall biogenesis. The binding model suggested one or more hydrogen bonding and/or arene-H or arene-arene interactions between hydrazones or pyrazole-fused coumarin derivatives and InhA enzyme for all synthesized compounds.

Metal- and Catalyst-Free One-Pot Cascade Coupling of α-Enolic Dithioesters with in situ Generated 4-Chloro-3-formylcoumarin: Access to Thioxothiopyrano[3,2-c]chromen-5(2H)-ones

An efficient and viable one-pot protocol for the synthesis of a specific class of 2-thioxothiopyrano[3,2-c] chromen-5(2H)-ones has been devised by the cross-coupling of 4-hydroxycoumarin and α-enolic dithioesters under metal- and additive-free conditions in open air. The reaction proceeds via in situ generation of 4-chloro-3-formylcoumarin followed by consecutive Michael-type addition/intramolecular cyclization/ elimination cascade, enabling the creation of thiopyran-2-thione ring over coumarin framework through successive formation of C?C and C?S bonds. Remarkably, the benign conditions, atom-economy, and quantifying forbearance of a wide horizon of functional groups are added characteristics to this strategy. (Figure presented.).

Spectroscopic, invitro antibacterial, and antifungal studies of Co(II), Ni(II), and Cu(II) complexes with 4-chloro-3-coumarinaldehyde Schiff bases

A series of metal complexes ML2 2H2O [M = Co(II), Ni(II), and Cu(II)] have been synthesized with Schiff bases derived from 3-substituted-4-amino-5-mercapto-1,2,4-triazole and 4-chloro-3-coumarinaldehyde. The structures of these metal complexes have been proposed from elemental analyses, spectral (IR, UV-Vis, FAB-mass, ESR, and fluorescence), magnetic, and thermal studies. Low molar conductance values in DMF indicate that the metal complexes are non-electrolytes. Cyclic voltammetric studies suggested that the Ni(II) and Cu(II) complexes are single-electron transfer quasi-reversible. The Schiff bases and their metal complexes have been screened for invitro antibacterial (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Salmonella typhi) and antifungal activities (Candida albicans, Cladosporium, and Aspergillus niger) by the minimum inhibitory concentration method. The Schiff base I and its Co(II) and Ni(II) complexes exhibit DNA cleavage activity on isolated DNA of S. aureus and A. niger.

One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multicomponent reactions and their molecular switching properties

Two new pyranocoumarins were synthesized via one-pot, microwave-assisted pseudo multicomponent condensations of coumarin and 4-methylquinoline to investigate their molecular switching properties. Both are light-sensitive and have a distinct change of color upon UV irradiation. The reaction can be reverted by treating the photogenerated products with imidazoline-functionalized magnetic nanoparticles, which can be swiftly recycled with an external permanent magnet.

A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative

Thermolysis of a coumarin trichloroacetimidate yields a single rearrangement product. The proposed mechanism is a pseudopericyclic allowed (Woodward-Hoffman forbidden) [3,5]-sigmatropic rearrangement to form the corresponding amide followed by a sigmatropic [1,5]-hydrogen migration. Transition state calculations at the B3LYP/6-31G(d,p) level support this mechanism and suggest the selectivity is influenced by the stability of the intermediates.

Coordination chemistry of rare earth metal complexes with coumarin-based imines: Ecofriendly synthesis, characterization, antimicrobial, DNA cleavage, pesticidal, and nematicidal activity evaluations

Coordination and biocidal aspects of lanthanide(III) complexes with 3-formyl-4-chlorocoumarin hydrazinecarbothioamide (L1H) and 3-formyl-4-chlorocoumarin hydrazinecarboxamide (L2H) are described with the support of elemental analyses, molecular weight, melting point, and molar conductance determinations along with the IR, 1H NMR, EPR, UV spectral, and X-ray powder diffraction studies. The spectral data suggest that the ligands are monobasic bidentate, coordinating through nitrogen and sulfur/oxygen. The isolated products are colored solids, soluble in DMSO, DMF, and methanol. All the complexes are monomeric, as indicated by their molecular weight determinations. Conductivity measurements in dry DMF show them to be non-electrolytes. The antimicrobial, DNA cleavage, pesticidal, and nematicidal activities were examined and are discussed. Copyright

Coumarin based colorimetric and fluorescence on-off chemosensor for F?, CN? and Cu2 + ions

(E)-4-Chloro-3-[{2-(4-nitrophenyl)hydrazono}methyl]-2H-chromen-2-one (C), a coumarin derivative has been studied toward its ion sensing properties for F?, CN? and Cu2 +. A proton-transfer mechanism for F? sensing has been deduced with the help of 1H NMR titration alongwith from the changes in the absorption and emission spectra of C in the presence of F?. C formed 1:1 stoichiometric complex with each of these analytes. Sensing of C toward Cu2 + is poor, but interestingly in the presence of F? or CN? the sensing ability of Cu2 + gets enhanced many folds, and C can act as F? or CN? mediated off-on sensor for Cu2 +. Moreover, colorimetric strip (pre-coated with the coumarin derived compound) tests for F? and CN? from their DMSO solution at high temperature (~ 100 °C) opens up the door for easiest naked eye recognition and distinction of these ions, and also for naked-eye detection of F? and CN? from its aqueous solution at high temperature (~ 100 °C).

Discovery of chromeno[4,3-c]pyrazol-4(2H)-one containing carbonyl or oxime derivatives as potential, selective inhibitors PI3Kα

A series of novel chromeno[4,3-c]pyrazol-4(2H)-one containing carbonyl or oxime derivatives (4a-n, 5a-n) have been synthesized and evaluated their biological activities as phosphatidyl inositol 3-kinase (PI3K) inhibitors. Out of them, compound 5l showed the most potent antiproliferative activities against HCT-116 with IC50 of 0.10 μM in vitro, and exhibited the most potent activity for PI3Kα with the value of 0.012 μM. Docking simulation of 5l into PI3Kα active site were performed to determine the probable binding model, and it indicated that compound 5l could be optimized as a potential inhibitor of PI3Kα in the further study.

An efficient synthesis of 4-substituted coumarin derivatives via a palladium-catalyzed Suzuki cross-coupling reaction

An efficient Pd-catalyzed Suzuki cross-coupling reaction of sterically crowded 4-chlorocoumarin derivatives with air- and moisture-stable potassium organotrifluoroborates is developed. This methodology has been used to generate a series of novel alkyl, ar

Synthesis, spectroscopic characterization, antimicrobial, pesticidal and nematicidal activity of some nitrogen-oxygen and nitrogen-sulfur donor coumarins based ligands and their organotin(IV) complexes

Series of new tin complexes are synthesized by classical thermal and microwave-irradiated techniques. The biologically potent ligands 3-formyl-4-chlorocoumarin semicarbazone (L1H) and 3-formyl-4-chlorocoumarin thiosemicarbazone (L2H), were prepared by the condensation of semicarbazide hydrochloride and thiosemicarbazide in ethanol with the particular ketone by using microwave as well as conventional methods. The tin(IV) complexes have been prepared by mixing Ph3SnCl/Me 3SnCl/Me2SnCl2 in 1:1 and 1:2 molar ratios with monofunctional bidentate ligands. The structures of the ligands and their tin complexes were confirmed by the elemental analysis, melting point determinations, molecular weight determinations, IR, 1H NMR, 13C NMR, 119Sn NMR, UV, mass spectral and X-ray powder diffraction studies. On the basis of these studies it is clear that the ligands coordinated to the metal atom in a monobasic bidentate mode, by X ∩ N donor system. Thus, suitable trigonal bipyramidal geometry for penta-coordinated state and octahedral geometry for hexa-coordinated state have been suggested for the 1:1 and 1:2 metal compounds. Both the ligands and their complexes have been screened for their antimicrobial, pesticidal and nematicidal activities. Copyright

Syntheses, characterization, antimicrobial and DNA cleavage activity of Cr(III) complexes with coumarin based schiff base ligands

A series of biologically important complexes of chromium(III) have been synthesized by the reaction of 3-formyl-4-chlorocoumarin hydrazinecarbothioamide (L1H) and 3-formyl-4-chlorocoumarin hydrazinecarboxamide (L2H) with CrCl3·6H2O in 1:1 and 1:2 molar ratio. All the complexes have been characterized by elemental analysis, molecular weight determination, melting point, conductivity measurements, electronic, IR, 1H NMR, 13C NMR and EPR spectroscopic techniques and X-ray diffraction. In vitro biological screening effects of the compounds were tested against the pathogenic bacterial and fungal species. Further, free ligands and their metal complexes have been screened for their DNA cleavage activity. A comparative study of the biological activities of the Schiff base ligands and their Cr(III) complexes indicates that the complexes exhibit higher antimicrobial and DNA cleavage activity than the free ligands. Physicochemical studies and spectral data suggested a hexa-coordinated environment around the central metal ion.

Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates

Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.