5406-57-5

Usage

Uses

Used in Chemical Synthesis:
ETHYL 4-TERT-BUTYLBENZOATE is used as an intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical industries. Its unique structure allows for further functionalization and modification, making it a versatile building block for the development of new molecules with specific biological activities.
Used in Plastics and Polymers:
In the plastics and polymer industry, ETHYL 4-TERT-BUTYLBENZOATE is used as a plasticizer and additive to improve the flexibility, workability, and durability of various polymers. Its compatibility with a wide range of polymers and its ability to enhance their mechanical properties make it a valuable component in the formulation of plastics and polymers.
Used in Coatings and Adhesives:
ETHYL 4-TERT-BUTYLBENZOATE is also utilized in the coatings and adhesives industry as a solvent and additive. Its ability to dissolve a variety of resins and polymers makes it an effective component in the formulation of coatings and adhesives, enhancing their performance and durability.
Used in Fragrances and Flavors:
Due to its pleasant odor and compatibility with other fragrance ingredients, ETHYL 4-TERT-BUTYLBENZOATE is used as a fixative and solvent in the fragrance and flavor industry. It helps to stabilize and prolong the scent of perfumes and other fragrance products, as well as enhance the taste and aroma of various food and beverage products.
Used in Cosmetics and Personal Care:
In the cosmetics and personal care industry, ETHYL 4-TERT-BUTYLBENZOATE is used as a solvent, emollient, and preservative in various formulations, such as creams, lotions, and shampoos. Its ability to improve the texture, stability, and shelf life of these products makes it a valuable ingredient in the development of cosmetics and personal care products.
Used in Photochemistry:
ETHYL 4-TERT-BUTYLBENZOATE is employed in the field of photochemistry as a photostabilizer and UV absorber. Its ability to absorb ultraviolet radiation and protect materials from photodegradation makes it an essential component in the formulation of sunscreens, plastics, and other materials that require protection from UV-induced damage.

InChI:InChI=1/C13H18O2/c1-5-15-12(14)10-6-8-11(9-7-10)13(2,3)4/h6-9H,5H2,1-4H3

Upstream product

• 93-89-0 benzoic acid ethyl ester 
• 89379-02-2 tert-butylmercury iodide 
• 558-17-8 tert-Butyl iodide 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 677-22-5 tert-butylmagnesium chloride 
• 64-17-5 ethanol 
• 1710-98-1 p-tert-butyl benzoyl chloride 
• 98-51-1 4-tert-butyltoluene 
• 877-65-6 p-tert-butylbenzyl alcohol 
• 63488-10-8 4-tert-butylmagnesium bromide 
• 541-41-3 chloroformic acid ethyl ester 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 383-63-1 ethyl trifluoroacetate, 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 

Downstream Products

• 57139-21-6 potassium 4-(tert-butyl)benzohydroxamate 
• 125952-12-7 4-tert-butyl-1-(1-ethoxyvinyl)benzene 
• 943-27-1 4'-t-butylacetophenone 
• 1309382-87-3 1-(2-chloro-5-thiazolylmethyl)-3-methyl-5-(-4-tert-butyl benzamido)-1,3,5-hexahydrotriazine-2-N-nitroimine 
• 306936-90-3 5-(4-(tert-butyl)phenyl)-1,3,4-oxadiazole-2-thiol 
• 1260218-14-1 2-(4-(tert-Butyl)phenyl)-5-((2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazole 
• 39528-62-6 3-(4-tert-butylphenyl)-3-oxopropanenitrile 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Selective inhibition of Rhizopus eumelanin biosynthesis by novel natural product scaffold-based designs caused significant inhibition of fungal pathogenesis

Melanin is a dark color pigment biosynthesized naturally in most living organisms. Fungal melanin is a major putative virulence factor of Mucorales fungi that allows intracellular persistence by inducing phagosome maturation arrest. Recently, it has been shown that the black pigments of Rhizopus delemar is of eumelanin type, that requires the involvement of tyrosinase (a copper-dependent enzyme) in its biosynthesis. Herein, we have developed a series of compounds (UOSC-1-14) to selectively target Rhizopus melanin and explored this mechanism therapeutically. The compounds were designed based on the scaffold of the natural product, cuminaldehyde, identified from plant sources and has been shown to develop non-selective inhibition of melanin production. While all synthesized compounds showed significant inhibition of Rhizopus melanin production and limited toxicity to mammalian cells, only four compounds (UOSC-1, 2, 13, and 14) were selected as promising candidates based on their selective inhibition to fungal melanin. The activity of compound UOSC-2 was comparable to the positive control kojic acid. The selected candidates showed significant inhibition of Rhizopus melanin but not human melanin by targeting the fungal tyrosinase, and with an IC50 that are 9 times lower than the reference standard, kojic acid. Furthermore, the produced white spores were phagocytized easily and cleared faster from the lungs of infected immunocompetent mice and from the human macrophages when compared with wild-type spores. Collectively, the results suggested that the newly designed derivatives, particularly UOSC-2 can serve as promising candidate to overcome persistence mechanisms of fungal melanin production and hence make them accessible to host defenses.

Construction of Esters through Sulfuryl Fluoride (SO 2 F 2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO 2 F 2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

Microwave-assisted synthesis method for ethylation reaction

The invention relates to a microwave-assisted synthesis method for an ethylation reaction. The method is characterized in that a reaction substrate is in an organic solvent, trifluoroacetic acid ethyl ester is taken as an ethylation reagent, in the presence of an alkali, microwave-assisted heating is carried out for 2 minutes, and a corresponding ethylation product can be obtained. The invention provides a new method for the ethylation reaction. The reaction rate of the method is several times higher than that of a traditional method, the operation is simple and convenient, the cost is low, the reaction time is short, the application range of the substrate is wide, the use of the expensive or hypertoxic ethylation reagent can also be avoided, and the method has higher application value.

Ligand-free nickel-catalyzed Kumada couplings of aryl bromides with tert-butyl Grignard reagents

A ligand-free nickel-catalyzed Kumada cross-coupling of aryl bromides and tert-butyl Grignard reagents led to the formation of a series of tert-butyl aryls in moderate to good yields, excellent tBu/iBu ratios, and good functional group compatibility. A radical coupling process is indicated and a mechanism with a Ni(I)-Ni(III) catalytic cycle is proposed.

Benzo polyaza and phosphole oxygen ligand and complex containing same, preparation method and application

The invention discloses a benzo polyaza and phosphole oxygen ligand and a complex containing same, a preparation method and application. The invention provides a benzo polyaza and phosphole oxygen ligand as shown in formula I and a complex containing same. A complex of the benzo polyaza and phosphole oxygen ligand and a transition metal halide enables direct coupling of carbon-carbon bonds betweenbig steric hindrance alkyl and aryl; the reaction conditions are gentle; the catalyzing efficiency is high; the coupling reaction process of the carbon-carbon bonds between big steric hindrance alkyland aryl can be extremely simplified; the practicability is high; the reaction cost can be obviously decreased, and the reaction period is reduced; the complex is free from other side products without being required in the catalyzing process. The formula refers to the description.

Inhibitory growth evaluation and apoptosis induction in MCF-7 cancer cells by new 5-aryl-2-butylthio-1,3,4-oxadiazole derivatives

Background: Cancer has become one of the global health issues and it is the life-threatening disease characterized by unrestrained growth of cells. Despite various advances being adopted by chemotherapeutic management, the use of the current anticancer drugs such as Doxorubicin, Asparginase, Methotrexate, Vincristine remains limited due to high toxicity, side effects and developing drug resistance. Apoptosis is a crucial cellular process and improper regulation of apoptotic signaling pathways may lead to cancer formation. Subsequently, the synthesis of effective chemotherapeutic agents that can induce apoptosis in tumor cell has emerged as a significant approach in cancer drug discovery. Methods: The goal of this work is to develop a potential antitumor agent exerting significant inhibitory effects on cancer cell and low cytotoxicity, for which we focused on the structural features of 1,3,4-oxadiazoles as it a privileged scaffold in modern medicinal chemistry and have the ability to inhibit growth factors, enzymes and kinases potentially involved in the attainment of cellular immortality and carcinogenesis. Result: In vitro MTT screening assay showed the compound 5-aminophenyl-2-butylthio-1,3,4-oxadiazole (5e) showing the highest inhibitory effect against MCF-7 cancer cell with IC50 value 10.05?±?1.08?μM while it is much safer and less toxic on normal cell line (HEK-293). The dose-dependent treatment of MCF-7 cells with 5e resulted in inhibition of cell migration in the wound healing assay. The flow-cytometry analysis showed the cells arrested in G0/G1 phase of the cell cycle. Compound 5e induced apoptosis of MCF-7 cells was characterized using DAPI staining and Annexin V-PE/7-AAD dual binding assay. Reduction of NBT by compound 5e showed a reduced generation of ROS. Western blotting studies showed high activation of apoptotic protein Caspase3 and decrease in expression of anti-apoptotic protein BCL-2. Conclusion: Based on the results of in vitro studies, it could be concluded that compound 5e showed a significant inhibitory growth effect on MCF-7 cells and have the potential to be developed as lead molecule and further structural modifications may result in promising new anticancer agents.

An N-heterocyclic carbene-based nickel catalyst for the Kumada–Tamao–Corriu coupling of aryl bromides and tertiary alkyl Grignard reagents

In this study, nickel-catalyzed coupling reactions between arylhalides and tert-alkyl Grignard reagents were developed. Our original bicyclic NHC ligands reduced the formation of isomerized products, and we found that NMP as a co-solvent suppressed the reduction process. Under the optimal conditions we developed, the catalyst loading was lowered to 0.5?mol?%, and catalyst loading using ortho-substituted aryl bromides was also applicable at the level of 2.0?mol?%.

Reactivity of mixed organozinc and mixed organocopper reagents: 12. Three component reaction of mixed (n-alkyl)(diaryl)zincates, chloroformates and phosphines for the synthesis of esters

The reaction of mixed n-butyldiphenylzincate, n-BuPh2ZnMgBr with ethyl chloroformate, ClCOOEt in the presence n-Bu3P in THF takes place with quantitative yield and phenyl group transfer to give PhCOOEt. Ethoxycarbonylation of n-BuPh2ZnMgBr is preferable to the reaction of PhMgBr forming ester and triphenylcarbinol and also to the reaction of triphenylzincate, Ph3ZnMgBr for atom economy. Group selectivity in the phosphine catalyzed C-COOR coupling of n-BuPh2ZnMgBr and n-Bu2PhZnMgBr can be controlled by changing reaction parameters. n-Bu3P catalyzed reaction of n-BuPh2ZnMgBr with ClCOOEt takes place with phenyl selectivity whereas reaction of n-Bu2PhZnMgBr with ClCOOPh results in n-butyl transfer. Catalysis by Ph3P increases n-butyl group:phenyl group transfer ratio in the ethoxycarbonylation of both zincates. Selective transfer of aryl groups in n-Bu3P catalyzed reaction of n-butyl(aryl)2ZnMgBr reagents with ClCOOEt in THF provides a new procedure for the organometallic synthesis of arenecarboxylic acid ethyl esters at room temperature.

Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides

Efficient synthetic procedures for the preparation of acid hydrazines and hydrazides were developed by converting the corresponding carboxylic acid into the methyl ester catalyzed by Amberlyst-15, followed by a reaction with hydrazine monohydrate. Sulfohydrazides were prepared from the corresponding sulfonyl chlorides and hydrazine monohydrate. Both of these group of compounds were condensed with substituted salicylaldehydes using gradient concentration methods that generated a large library of hydrazone, hydrazide and sulfohydrazide analogs. Antifungal activity of the prepared analogs showed that salicylaldehyde hydrazones and hydrazides are potent inhibitors of fungal growth with little to no mammalian cell toxicity, making these analogs promising new targets for future therapeutic development.