20651-69-8

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-BUTYLBENZOATE is used as a key intermediate in the synthesis of fluconazole analogs, which are a class of antifungal agents. These analogs exhibit potent antifungal activity against a wide range of fungal pathogens, making them valuable for the development of new antifungal drugs.
Used in Chemical Synthesis:
METHYL 4-BUTYLBENZOATE is used as a versatile building block in the preparation of various substituted heterocyclic compounds. Its reactivity and functional groups make it suitable for a range of chemical reactions, allowing for the synthesis of diverse chemical entities with potential applications in various fields.

InChI:InChI=1/C12H16O2/c1-3-4-5-10-6-8-11(9-7-10)12(13)14-2/h6-9H,3-5H2,1-2H3

Upstream product

• 542-69-8 1-iodo-butane 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 76322-80-0 methyl 4-(3-oxobut-1-enyl)benzoate 
• 28788-62-7 4-butylbenzoyl chloride 
• 124-41-4 sodium methylate 
• 109-72-8 n-butyllithium 
• 51207-43-3 methyl 4-(tosyloxy)benzoate 
• 161497-18-3 methyl 4-(methanesulfonyloxy)benzoate 
• 6638-68-2 4,5-dimethyl-2-phenyl-1,3,2-dioxaborolane 
• 215877-38-6 4,5-dimethyl-2-(4-methoxyphenyl)-1,3,2-dioxaborolane 
• 215877-30-8 4,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborolane 
• 67-56-1 methanol 
• 20651-71-2 4-butyl benzoic acid 
• 15499-27-1 4-n-butylchlorobenzene 

Downstream Products

• 1595-05-7 p-butyltoluene 
• 80361-60-0 methyl ester of trans 4-butylcyclohexanecarboxylic acid 
• 80361-47-3 methyl ester of cis 4-butylcyclohexanecarboxylic acid 
• 1620-30-0 diphenyl(pyridin-4-yl)methanol 
• 1449763-69-2 3-acetyl-5-(4-n-butyl-phenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro-1,3,4-oxadiazole 
• 935559-50-5 4-butyl-N’-((5-nitrofuran-2-yl)methylene)benzohydrazide 
• 314753-72-5 C₁₂H₁₇N₃OS 
• 1499949-66-4 C₁₂H₁₅N₃S 
• 1452784-08-5 C₁₂H₁₄N₂OS 
• 1452784-18-7 C₁₅H₁₆N₂OS 
• 1452784-01-8 C₂₆H₂₆F₂N₈O₂S 
• 160505-17-9 methyl 4-(1-bromobutyl)benzoate 

Relevant academic research and scientific papers

A Path to More Sustainable Catalysis: The Critical Role of LiBr in Avoiding Catalyst Death and its Impact on Cross-Coupling

The role that LiBr plays in the lifetime of Pd-NHC complexes has been investigated. A bromide ion is proposed to coordinate to Pd thereby preventing beta hydride elimination (BHE) (to form NHC-H+) of the reductive elimination (RE) intermediate that normally completes with the desired cross-coupling catalytic cycle. Coordinating groups, such as anilines, are able to bind suitably well to Pd to prevent this pathway from occurring, thus reducing the need for the added salt. The metal hydride formed from BHE is very unstable and RE of the hydride to the NHC ligand occurs very rapidly giving rise to the corresponding hydrido-NHC (i.e., NHC-H+). The use of the per deuterated dibutylzinc shows a significant deuterium isotope effect, shutting down catalyst death almost completely. The use of bis-neopentylzinc, now possessing no hydrides, eliminates catalyst death all together leading to a very long-lived catalytic cycle and confirming the untoward role of BHE.

The Role of LiBr and ZnBr2 on the Cross-Coupling of Aryl Bromides with Bu2Zn or BuZnBr

The impact of LiBr and ZnBr2 salts on the Negishi coupling of alkylZnBr and dialkylzinc nucleophiles with both electron-rich and -poor aryl electrophiles has been examined. Focusing only on the more difficult coupling of deactivated (electron-rich) oxidative addition partners, LiBr promotes coupling with BuZnBr, but does not have such an effect with Bu2Zn. The presence of exogenous ZnBr2 shuts down the coupling of both BuZnBr and Bu2Zn, which has been shown before with alkyl electrophiles. Strikingly, the addition of LiBr to Bu2Zn reactions containing exogenous ZnBr2 now fully restores coupling to levels seen without any salt present. This suggests that there is a very important interaction between LiBr and ZnBr2. It is proposed that Lewis acid adducts are forming between ZnBr2 and the electron-rich Pd0 centre and the bromide from LiBr forms inorganic zincates that prevent the catalyst from binding to ZnBr2. This idea has been supported by catalyst design as chlorinating the backbone of the NHC ring of Pd-PEPPSI-IPent to produce Pd-PEPPSI-IPentCl catalyst now gives quantitative conversion, up from a ceiling of only 50 % with the former catalyst.

INDOLE DERIVATIVES USEFUL AS GLUCAGON RECEPTOR ANTAGONISTS

The present invention is directed to indole derivatives, pharmaceutical compositions containing them and their use in the treatment and/or prevention of disorders and conditions ameliorated by antagonizing one or more glucagon receptors, including for example metabolic diseases such as Type II diabetes mellitus and obesity.

Synthesis of 3-Arylbenzofuran-2-ylphosphines via Rhodium-Catalyzed Redox-Neutral C-H Activation and Their Applications in Palladium-Catalyzed Cross-Coupling of Aryl Chlorides

A new class of aryl-heteroarylphosphines, 3-arylbenzofuran-2-ylphosphines, was synthesized by [Cp?Rh(III)]-catalyzed redox-neutral cyclization of N-phenoxyacetamides with 1-alkynylphosphine sulfides and oxides followed by reduction. This step-economic reaction proceeds in excellent regioselectivity with a broad substrate scope. The application of the resulting air-stable trivalent-phosphine containing dicyclohexylphosphino moiety in palladium-catalyzed Suzuki-Miyaura coupling and Buchwald-Hartwig amination of aryl chlorides is also described.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides

A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o -borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions.

Copper-Catalyzed O-Methylation of Carboxylic Acids Using DMSO as a Methyl Source

A copper-catalyzed O-methylation of carboxylic acids using dimethyl sulfoxide (DMSO) as the methyl source is disclosed. This transformation exhibits a broad substrate scope and excellent functional group tolerance. Mechanistic studies indicate that a methyl radical is generated from dimethyl sulfoxide in the reaction process.

Single-Electron-Transfer-Induced Coupling of Alkylzinc Reagents with Aryl Iodides

Alkylzinc reagents prepared from an alkyllithium and zinc iodide were found to undergo coupling with aryl and alkenyl iodides in the presence of LiI in a mixed solvent consisting of THF and diglyme (1:1). Alkyllithiums, prepared by halogen–lithium exchange between an alkyl iodide and tert-butyllithium, are also converted to alkylarenes through alkylzinc reagents.

New Fluorescence Domain "excited Multimer" Formed upon Photoexcitation of Continuously Stacked Diaroylmethanatoboron Difluoride Molecules with Fused π-Orbitals in Crystals

The crystal-packing structures of seven derivatives of diaroylmethanatoboron difluoride (1 a-gBF2) are characterized by no overlap of the π-conjugated main units of two adjacent molecules (typeI), overlap of the benzene ring π-orbitals of two adjacent molecules (typeII), and overlap of the benzene and dihydrodioxaborinine rings π-orbitals of adjacent molecules (typeIII). The crystal-packing structures govern the fluorescence (FL) properties in the crystalline states. The FL domain that is present in typeI crystals, in which intermolecular orbital interactions are absent, leads to excited monomer-like FL properties. In the case of the typeII crystals, the presence of intermolecular overlap of the benzene rings π-orbitals generates new FL domains, referred to as "excited multimers", which possess allowed S0-S1 electronic transitions and, as a result, similar FL lifetimes at longer wavelengths than the FL of the typeI crystals. Finally, intermolecular overlap of the benzene and dihydrodioxaborinine ring π-orbitals in the typeIII crystals leads to "excited multimer" domains with forbidden S0-S1 electronic transitions and longer FL lifetimes at similar wavelengths as that in typeI crystals.

CROSS-COUPLING OF UNACTIVATED SECONDARY BORONIC ACIDS

Provided are methods for site- and stereo-retentive cross-couplings with unactivated secondary boronic acids, particularly useful in building block-based approach for small molecule synthesis. Also provided is a method of forming an air-stable chiral secondary boronic acid.

Synthesis, characterization, and anticancer studies of S and N alkyl piperazine-substituted positional isomers of 1,2,4-triazole derivatives

A series of 3-[3-[4-(substituted)-1-cyclicamine] propyl]thio-5- substituted[1,2,4]triazoles (8a-m) and 2-[3-[4-(substituted)-1-cyclicamine] propyl]-5-(substituted)-2,4-dihydro-3H[1,2,4]triazole-3-thiones (9a-h) were synthesized with good yields starting from corresponding carboxylic acids using two different methods. The cytotoxicity studies of these derivatives were studied against five different human cancer cell lines. Six compounds had shown good anticancer activity. The triazole derivatives, 9d, 8j, and 8i were most potent particularly against U937 and HL-60 cells. The cytotoxic potency of the compounds varied between the cell lines suggesting that a structural property of these compounds as possible determinant of their biological activity. Springer Science+Business Media 2013.