38409-63-1

Usage

General Description

4-Hexylbenzoic acid methyl ester is a chemical compound with the molecular formula C16H22O2. It is commonly used as a fragrance ingredient in various consumer products such as perfumes, lotions, and soaps. This colorless to pale yellow liquid is derived from benzoic acid and hexyl alcohol and is characterized by its sweet, floral odor. It is also known for its ability to act as a solvent and can be found in some industrial applications such as adhesives and coatings. Additionally, it is considered to be relatively stable under normal conditions and has a low potential for toxicity, making it a frequently used additive in the cosmetic and personal care industry.

InChI:InChI=1/C14H20O2/c1-3-4-5-6-7-12-8-10-13(11-9-12)14(15)16-2/h8-11H,3-7H2,1-2H3

Upstream product

• 1126-46-1 Methyl 4-chlorobenzoate 
• 42371-64-2 9-hexyl-9-borabicyclo[3.3.1]nonane 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 3761-92-0 n-hexylmagnesium bromide 
• 619-44-3 methyl 4-iodobenzoate 
• 51207-43-3 methyl 4-(tosyloxy)benzoate 
• 17763-71-2 4-carbomethoxyphenyl triflate 
• 74-11-3 para-chlorobenzoic acid 
• 44767-62-6 n-hexylmagnesium chloride 
• 110-54-3 hexane 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 67-56-1 methanol 
• 21643-38-9 4-hexylbenzoic acid 
• 905966-40-7 methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 

Downstream Products

• 64328-58-1 4-hexylbenzohydrazide 

Relevant academic research and scientific papers

Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Photocatalyst in the Dual Catalytic Arylation of Alkyl Bis(catecholato)silicates

Mesoporous graphitic carbon nitride (mpg-CN) is introduced as a heterogeneous photocatalyst to perform dual photoredox- and nickel-catalyzed cross-coupling reactions between alkyl bis(catecholato)silicates as radical precursors and aryl or alkenyl bromides. The synergy between this recyclable photocatalyst and the broadly applied homogeneous nickel complex [Ni(dtbbpy)Br2] gives access to C(sp2)-C(sp3) cross-coupling products in a sustainable fashion. The recycled mpg-CN photocatalyst was analyzed by time-resolved emission spectroscopy and EPR spectroscopy.

Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling

Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

Hydrodecyanation of Secondary Alkyl Nitriles and Malononitriles to Alkanes using DiMeImd-BH3

The decyanation of secondary aliphatic nitriles and the 2-fold decyanation of malononitriles leading to alkanes in the presence of 1,3-dimethylimidazol-2-ylidene borane (diMeImd-BH3) are reported. These reactions proceed via a radical mechanism that involves the addition of a borane radical to the nitrile to form an iminyl radical, followed by cleavage of a carbon-carbon bond. Theoretical calculations suggest that the β-cleavage of these iminyl radicals, which affords NHC-BH2CN and the corresponding alkyl radicals, is the rate-determining step in this reaction.

Ni-catalyzed Reductive Deaminative Arylation at sp3 Carbon Centers

A Ni-catalyzed reductive deaminative arylation at unactivated sp3 carbon centers is described. This operationally simple and user-friendly protocol exhibits excellent chemoselectivity profile and broad substrate scope, thus complementing existing metal-catalyzed cross-coupling reactions to forge sp3 C-C linkages. These virtues have been assessed in the context of late-stage functionalization, hence providing a strategic advantage to reliably generate structure diversity with amine-containing drugs.

Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides

A new robust methodology for gram-scale iron-catalyzed cross-coupling between alkyl Grignard reagents and alkenyl or aryl halides is developed. This method does not require toxic additives such as NMP or expensive ligands. Its efficiency relies on the use of simple alkoxide magnesium salts as additives. On the basis of these results, a new procedure for one-pot synthesis of substituted benzamides from chloroesters is also proposed.

Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida

A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.

Nickel-catalyzed selective oxidative radical cross-coupling: An effective strategy for inert Csp3-H functionalization

An effective strategy for inert Csp3-H functionalization through nickel-catalyzed selective radical cross-couplings was demonstrated. Density functional theory calculations were conducted and strongly supported the radical cross-coupling pathway assisted by nickel catalyst, which was further confirmed by radical-trapping experiments. Different arylborates including arylboronic acids, arylboronic acid esters and 2,4,6-triarylboroxin were all good coupling partners, generating the corresponding Csp3-H arylation products in good yields.

Olefin-assisted iron-catalyzed alkylation of aryl chlorides

A selective and operationally simple ironcatalyzed cross-coupling of aryl chlorides with alkylmagnesium halides has been developed. The reaction tolerates various functional groups and exhibits high chemoselectivity even in the presence of aryl bromides. Mechanistic studies indicate the essential role of the olefin substituent for substrate activation. Competing polymerization and reduction are effectively suppressed.