108530-10-5

Basic information

• Product Name: 7-Coumaryl Triflate
• Synonyms: 7-Coumaryl Triflate;1,1,1-Trifluoro-Methanesulfonic Acid 2-Oxo-2H-1-benzopyran-7-yl Ester;2-Oxo-2H-chromen-7-yl Trifluoromethanesulfonate;2-Oxo-2H-chromen-7-yl Trifluoromethanesulfonate;2-Oxo-2H-chromen-7-yl trifluormethanesulfonate
• CAS NO: 108530-10-5
• Molecular Formula: C₁₀H₅F₃O₅S
• Molecular Weight: 294.2039096
• Product Categories: Aromatics;Heterocycles;Aromatics, Heterocycles
• Mol File: 108530-10-5.mol

Chemical Properties

• Melting Point: 81.0 to 85.0 °C
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 7-Coumaryl Triflate(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Coumaryl Triflate(108530-10-5)
• EPA Substance Registry System: 7-Coumaryl Triflate(108530-10-5)

Safety Data

• Hazardous Substances Data: 108530-10-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
7-Coumaryl Triflate is used as a reagent in organic synthesis for its ability to facilitate specific chemical reactions. Its triflate group (-OTf) is particularly useful in promoting certain types of reactions, such as esterification, acylation, and other processes that require the transfer of the triflate group to another molecule.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7-Coumaryl Triflate is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its role in facilitating specific reactions can lead to the production of new drugs or the improvement of existing ones, contributing to advancements in medicinal chemistry.
Used in Chemical Research:
7-Coumaryl Triflate is also utilized in chemical research as a tool to study reaction mechanisms and to develop new synthetic methodologies. Its unique properties allow researchers to explore novel pathways and techniques in organic chemistry, potentially leading to more efficient and effective synthetic processes.
Used in Material Science:
In the field of material science, 7-Coumaryl Triflate can be employed in the synthesis of new materials with specific properties. Its use in organic synthesis can contribute to the development of materials with tailored characteristics for various applications, such as in electronics, coatings, or other industries.
Overall, 7-Coumaryl Triflate is a multifaceted compound with applications spanning across different industries, primarily due to its role in organic synthesis and its ability to enable specific chemical reactions. Its versatility and the potential for further research and development make it a valuable asset in the fields of chemistry and material science.

Upstream product

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 531-59-9 7-methoxycoumarin 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 108-46-3 recorcinol 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 

Downstream Products

• 91-64-5 coumarin 
• 190788-61-5 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-chromen-2-one 
• 19063-56-0 7-bromo-2-oxo-2H-chromene 
• 270088-04-5 7-ethynyl-2H-chromen-2-one 
• 1198091-32-5 C₂₀H₁₈O₅ 
• 115560-43-5 7-phenyl-2H-chromen-2-one 
• 1259294-06-8 7-(p-tolyl)-2H-chromen-2-one 
• 1259294-09-1 7-(4-chlorophenyl)-2H-chromen-2-one 
• 1259294-08-0 7-(4-methoxyphenyl)-2H-chromen-2-one 
• 1259294-19-3 7-(4-hydroxyphenyl)-2H-chromen-2-one 

Relevant articles and documents

Activatable fluorescent probes for hydrolase enzymes based on coumarin-hemicyanine hybrid fluorophores with large Stokes shifts

We show that the equilibrium of intramolecular spirocyclization of coumarin-hemicyanine hybrid fluorophores can be finely tuned by means of chemical modifications. We used this scaffold to develop activatable fluorescent probes with large Stokes shifts for γ-glutamyltranspeptidase and esterase.

Meso-Phenyl-triazole bridged porphyrin-coumarin dyads: Synthesis, characterization and photophysical properties

Novel zinc (II) meso-phenyl-triazole bridged porphyrin-coumarin dyads have been synthesized in good to excellent yields through copper (I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of zinc (II) 5-(4-azidophenyl)-10,15,20-triphenylporphyrin with

Synthesis and antiproliferative activity of 3- and 7-styrylcoumarins

A series of styrylcoumarins were obtained via Mizoroki-Heck reactions between 3-bromo-4-methyl-7-(octyloxy)-2H-chromen-2-one or 2-oxo-2H-chromen-7-yl trifluoromethanesulfonate and functionalized styrenes. The structures of the products were elucidated by spectroscopic analysis. All compounds were evaluated against SW480 and CHO-K1 cell lines. A number of hybrids showed good antiproliferative activity. Among the tested compounds, hybrids 6e, 10c, and 10d, exhibited the highest activity (IC50- SW480/48h = 6,92; 1,01 and 5,33 μM, respectively) and selectivity (IS48h = >400; 67,8 and 7,2, respectively). In addition, these compounds were able to preserve their activities over time. The results achieved by these hybrids were even better than the lead compounds (coumarin and resveratrol) and the standard drug (5-FU). As regards structure-activity relationship it seems that the location of the styryl group on the coumarin structure and the presence of the hydroxyl group on the phenyl ring were determinant for the activity.

New carbazole derivatives including coumarin moiety for blue emitting materials

New carbazole derivatives including coumarin moiety, 7-(3-Carbazol-9-yl-phenyl)-chromen-2-one (C-PCa), 7-(9-Phenyl-9H-carbazol-3-yl)-chromen-2-one (PCa-C), 7-[9-(3-Carbazol-9-yl-phenyl)-9H-carbazol-3-yl]-chromen-2-one (PDCa-C) were synthesized by Suzuki reaction. A non-doped OLED was fabricated using the synthesized material as emitting materials. Among the three synthesized compounds, PDCa-C showed the highest efficiency with current efficiency of 1.34 cd/A and C.I.E of (0.18, 0.23) in the current density 10?mA/cm2.

Mechanism-based inactivation of cytochrome P450 2B1 by 7- ethynylcoumarin: Verification of apo-P450 adduction by electrospray ion trap mass spectrometry

7-Ethynylcoumarin was synthesized as a potential mechanism-based inhibitor, and it was found to be an effective inactivator of 7-ethoxy-4- (trifluoromethyl)coumarin (7EFC) O-deethylation catalyzed by purified, reconstituted P450 2B1. In contrast, 7-ethynylcoumarin demonstrated minimal inactivation of P450 2A6-mediated 7-hydroxycoumarin formation. The inactivation of P450 2B1 demonstrated pseudo-first-order kinetics and was NADPH- and inhibitor-dependent. The maximal rate constant for the inactivation of 2B1 was 0.39 min-1 at 30 °C, and thus, the time required to inactivate 50% of the P450 2B1 that was present (t( 1/2 )) was 1.8 min. The estimated concentration which led to half-maximal inactivation (K(I)) was 25 μM. No protection from inactivation was seen in the presence of nucleophiles (glutathione and sodium cyanide), an iron chelator (deferroxamine), or superoxide dismutase and catalase. Addition of the substrate (7EFC) protected P450 2B1 from inactivation, in a concentration-dependent manner. The partition ratio for P450 2B1 was 25; i.e., the number of metabolic events was 25-fold higher than the number of inactivating events. Incubations of 7- ethynylcoumarin with P450 2B1 for 10 min resulted in an 80% loss in enzymatic activity, while 90% of the ability to form a reduced-CO complex remained. This activity loss was not recovered following dialysis, indicative of irreversible inactivation. Covalent attachment of the entire inhibitor and oxygen to apo-P450 2B1, in a 1:1 ratio, was shown via electrospray ion trap mass spectrometry. This method also verified the absence of modification to the heme or the cytochrome P450 reductase. Taken together, the characterization of the inhibition seen with P450 2B1 and 7-ethynylcoumarin was consistent with all of the criteria required to distinguish a mechanism- based inactivator. In addition, electrospray ion trap mass spectrometry has the potential to be applied to protein adducts above and beyond those associated with the mechanism-based inactivation of cytochrome P450s.

Photocatalysis Enables Visible-Light Uncaging of Bioactive Molecules in Live Cells

The photo-manipulation of bioactive molecules provides unique advantages due to the high temporal and spatial precision of light. The first visible-light uncaging reaction by photocatalytic deboronative hydroxylation in live cells is now demonstrated. Using Fluorescein and Rhodamine derivatives as photocatalysts and ascorbates as reductants, transient hydrogen peroxides were generated from molecular oxygen to uncage phenol, alcohol, and amine functional groups on bioactive molecules in bacteria and mammalian cells, including neurons. This effective visible-light uncaging reaction enabled the light-inducible protein expression, the photo-manipulation of membrane potentials, and the subcellular-specific photo-release of small molecules.

Synthesis and antimycobacterial activity of 1-(β-D-Ribofuranosyl)-4-coumarinyloxymethyl- / -coumarinyl-1,2,3-triazole

A series of β-D-ribofuranosyl coumarinyl-1,2,3-triazoles have been synthesized by Cu-catalyzed cycloaddition reaction between azidosugar and 7-O-/7-alkynylated coumarins in 62–70% overall yields. The in vitro antimycobacterial activity evaluation of the s

Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore

In this study, we report a novel water-soluble umbelliferone-based fluorescent probe for hydrogen peroxide. This probe shows very large increases (up to 100-fold) in fluorescent intensity upon reaction with hydrogen peroxide, and good selectivity over other reactive oxygen species (ROS).

Coumarin Derivatives Exert Anti-Lung Cancer Activity by Inhibition of Epithelial–Mesenchymal Transition and Migration in A549 Cells

A series of coumarin derivatives and isosteres were synthesized from the reaction of triflic intermediates with phenylboronic acids, terminal alkynes, and organozinc compounds through palladium-catalyzed cross-coupling reactions. The in vitro cytotoxic ef

Compounds for treating spinal muscular atrophy

Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy. In a specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN2 into mRNA that is transcribed from the SMN2 gene. In another specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 into mRNA that is transcribed from the SMN1 gene. In yet another embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 and SMN2 into mRNA that is transcribed from the SMN1 and SMN2 genes, respectively.