19063-56-0

Usage

Uses

Used in Pharmaceutical Development:
2H-1-Benzopyran-2-one, 7-bromois used as a pharmaceutical precursor for the development of drugs targeting various diseases, particularly cancer. Its antitumor properties make it a promising candidate for the treatment of cancer, where it can potentially inhibit tumor growth and progression.
Used in Agrochemical Development:
In the agrochemical industry, 2H-1-Benzopyran-2-one, 7-bromois utilized as a starting material for the synthesis of compounds with pesticidal or herbicidal properties, contributing to the development of more effective and environmentally friendly agrochemicals.
Used in Organic Chemistry Research:
As a valuable building block in organic chemistry, 2H-1-Benzopyran-2-one, 7-bromois used in the synthesis of other organic compounds. Its unique structure and functional groups make it a versatile component in the creation of novel organic molecules for various applications, including the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 617-48-1 malic acid 
• 591-20-8 3-Bromophenol 
• 22532-62-3 4-bromosalicylaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 96-34-4 methyl chloroacetate 
• 858855-11-5 5-bromo-2-iodo-phenol 
• 292638-85-8 acrylic acid methyl ester 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 471-25-0 Propiolic acid 
• 1510865-23-2 5-bromo-2-ethenylphenol 
• 201230-82-2 carbon monoxide 
• 1438410-03-7 7-bromo-2-oxo-2H-chromene-3-carboxylic acid 
• 105837-04-5 7-bromo-2-oxo-2H-chromene-3-carboxylic acid ethyl ester 

Downstream Products

• 122086-86-6 7-methoxy-7',8-oxydicoumarin 
• 121884-04-6 8-methoxy-7,7'-oxydicoumarin 
• 2445-83-2 7-methylcoumarin 

Relevant academic research and scientific papers

Synthesis of Two Coumarins Isolated from Aster praealtus

Two coumarins isolated from Aster praealtus were synthesized via a direct coupling of the corresponding cyclohexyl carbinol with a coumarin-derived aryl bromide or iodide, a very difficult etherification due to the excess steric congestion around the carbinol and the low reactivity of the aryl halide that frustrated many seemingly feasible protocols. Unequivocal 1H and 13C NMR data for these compounds were thus made available for the first time. Uncertainty and errors in 1H and 13C NMR data in previous reports are also eliminated and revealed, respectively. These two long-known naturally occurring coumarins were synthesized via a direct coupling reaction, a very difficult etherification that frustrated many seemingly feasible protocols. Clear-cut spectroscopic data for these compounds were thus made available for the first time.

Natural Product Chemistry, Part 108. Synthesis of 7,7'-Oxy-dicoumarin, the Potential Precursor of Lasioerin and Gnidicoumarin (Short Communication)

The synthesis of 7,7'-oxy-dicoumarin from 7-hydroxycoumarin and 7-bromocoumarin via Ullmann synthesis is described.In contrast to the literature, from the reaction of m-bromophenol with 2-hydroxy succinic acid, 7-bromocoumarin as well as 5-bromocoumarin were obtained. - Keywords: 7,7'-Oxy-dicoumarin; Ullmann-synthesis; 7- and 5-Bromocoumarin

Visible-Light-Induced Direct Csp2-H Radical Trifluoroethylation of Coumarins with 1,1,1-Trifluoro-2-iodoethane (CF3CH2I)

Herein, we developed the first visible-light-induced direct Csp2-H radical 2,2,2-trifluoroethylation of coumarins with commercially available and cheap reagent CF3CH2I at room temperature. This transformation proceeded smoothly under mild conditions and showed excellent functional group compatibility. The synthetic value of the protocol was also demonstrated by the successful functionalization of several pharmaceuticals.

Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes

Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.

Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions

Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.

Isomers of Coumarin-Based Cyclometalated Ir(III) Complexes with Easily Tuned Phosphorescent Color and Features for Highly Efficient Organic Light-Emitting Diodes

Three Ir(CλN)2(acac)-type and one Ir(C1λN)(C2λN)(acac)-type coumarin-based cyclometalated Ir(III) complex isomers (IrC5, IrC7, IrC7-A, and IrC8) have been obtained using three coumarin-based isomers of 2-phenylpyridine (ppy)-type cyclometalating ligands (L-C5, L-C7, and L-C8). Two coordination isomers emerging as principal products (IrC7 and IrC7-A) are obtained in the synthesis of corresponding coumarin-based cyclometalated Ir(III) complexes because of two different coordination sites in ligand L-C7 to form a C-Ir bond. To the best of our knowledge, there are no such isomers reported to date. Interestingly, a broad range of phosphorescent color tuning from green (IrC8, λ = 516 nm) to red (IrC5, λ = 608 nm) has been realized through variation of the pyridyl substitution positions on the fused phenyl ring of the coumarin skeleton. In addition, based on natural transition orbital (NTO) analyses, features of the lowest triplet excited states (T1) from these coumarin-based cyclometalated Ir(III) complex isomers can be tuned easily by these ligand isomers as well. IrC5, IrC7, and IrC7-A show prevailing 3MLCT character associated with their T1 states which emit the phosphorescent signals, while the T1 state of IrC8 exhibits the dominant ligand-centered π-π? transition feature. Importantly, owing to the strong rigidity of the coumarin skeleton, all the coumarin-based cyclometalated Ir(III) complex isomers can show high phosphorescent quantum yields φp (ca. 0.4-1). Together with the improved electron-injection/electron-transport (EI/ET) ability, all the phosphorescent emitters display impressive electroluminescence (EL) performance. The device based on IrC8 gives the highest EL efficiencies of external quantum efficiency (ηext) 22.7%, current efficiency (ηL) 79.7 cd A-1, and power efficiency (ηP) 58.2 lm W-1, representing the most state-of-the-art EL ability ever achieved by coumarin-based phosphorescent emitters. All these encouraging data definitely suggest the great potential of the coumarin skeleton in both easy tuning of the photophysical properties of ppy-type Ir(III) phosphorescent complexes and developing high-performance phosphorescent emitters.

Organometallic iridium complex phosphorescent material containing coumarin skeleton and preparation method of phosphorescent material

An organometallic iridium complex phosphorescent material containing a coumarin skeleton and a preparation method of the phosphorescent material are disclosed. The coumarin skeleton is introduced intoa traditional 2-phenylpyridine ligand, and through controlling the change of substitution positions and adopting an asymmetric structure type, double regulation and control of the luminescent wavelength and luminous efficiency of an obtained iridium complex is realized, so that the organic electrophosphorescent material having simple structure and excellent performance is obtained. By using the characteristics that the coumarin skeleton structure is highly rigid, simple, easy to synthesize, strong in luminescent property and the like, double regulation and control of the luminescent wavelength and luminous efficiency of the obtained iridium complex is realized.

ORGANIC LIGHT-EMITTING DEVICE INCLUDING FLUORESCENT COMPOUND AND FLUORESCENT COMPOUND

An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer and a fluorescent compound, wherein the fluorescent compound comprises a 3n-π*-to-1π-π* energy transition from a 3n-π* excited state to a 1π-π* excited state, an energy level in a 1n-π* excited state of the fluorescent compound is greater than an energy level in the 1π-π* excited state of the fluorescent compound, the fluorescent compound emits a fluorescent light by radiative energy transition of an exciton in the 1π-π* excited state to a ground state, and the energy level in the 1n-π* excited state, the energy level in the 1π-π* excited state, and the energy level in the 3n-π* excited state are each independently calculated by using a time dependent-Density Functional Theory method.

Dicyanovinylcoumarin as a turn-on fluorescent sensor for cyanide ion

Dicyanovinylcoumarin chemosensors (4a, 4b and 4c) were designed and synthesized by the Knoevenagel condensation reaction. The electronic absorption and emission spectra of the dicyanovinylcoumarin isomers exhibited red shifted absorption and less emission as compared to their precursor's coumarin aldehydes. The sensing behavior of dicyanovinylcoumarin isomers were studied for different anions. In these dicyanovinylcoumarin isomers, the 7-substituted isomer shows high selectivity towards CN? in the presence of other F?, Cl?, Br?, I?, ClO4?, HSO4? and NO2? ions. The effect of CN? on the structure of dicyanovinylcoumarin isomer was studied by performing DFT calculations. The theoretical calculations show strong agreement with the experimental results. The detection limit for CN? were found to be 1.14 × 10?8 M for 7-substitued dicyanovinylcoumarin isomer 4b.