7155-12-6

Usage

Uses

Used in Fragrance Industry:
Heptylbenzoate is used as a fragrance ingredient for its ability to impart a fruity or floral scent to products, enhancing the sensory experience for consumers.
Used in Food Industry:
In the food industry, heptylbenzoate serves as a flavoring agent, adding unique taste profiles to various food products, thereby improving their overall appeal.
Used in Cosmetics and Personal Care Products:
Heptylbenzoate is used as a solvent in the production of cosmetics and personal care products, aiding in the formulation and stability of these products while also contributing to their scent.
Used in Household Cleaners:
In the household cleaning products industry, heptylbenzoate functions as a solvent, helping to dissolve other ingredients and improve the cleaning efficacy of the products.
Used in Paints and Coatings:
Heptylbenzoate is utilized in paints and coatings as a solvent, contributing to the application process and the final product's performance characteristics.
Used in Pharmaceutical Formulations:
In the pharmaceutical sector, heptylbenzoate is employed as a solvent in various formulations, assisting in the preparation and delivery of medications.
Overall, heptylbenzoate is a multifaceted chemical compound with applications spanning across fragrances, food, cosmetics, household products, industrial coatings, and pharmaceuticals, primarily due to its solvent properties and its ability to enhance the scent and flavor profiles of products.

InChI:InChI=1/C14H20O2/c1-2-3-4-5-9-12-16-14(15)13-10-7-6-8-11-13/h6-8,10-11H,2-5,9,12H2,1H3

Upstream product

• 111-70-6 n-heptan1ol 
• 93-89-0 benzoic acid ethyl ester 
• 629-04-9 1-Bromoheptane 
• 65-85-0 benzoic acid 
• 93-97-0 benzoic acid anhydride 
• 18132-93-9 heptanol trimethylsilyl ether 
• 132336-04-0 2-(heptyloxy)tetrahydro-2H-pyran 
• 98-88-4 benzoyl chloride 
• 55-21-0 benzamide 
• 100-53-8 phenylmethanethiol 
• 100-52-7 benzaldehyde 
• 96-09-3 styrene oxide 
• 108-86-1 bromobenzene 
• 93-58-3 benzoic acid methyl ester 

Relevant academic research and scientific papers

Mechanistic elucidation of monoalkyltin(iv)-catalyzed esterification

Monoalkyltin(iv) complexes are well-known catalysts for esterification reactions and polyester formation, yet the mode of operation of these Lewis acidic complexes is still unknown. Here, we report on mechanistic studies ofn-butylstannoic acid in stoichiometric and catalytic reactions, analyzed by NMR, IR and MS techniques. While the chemistry ofn-butyltin(iv) carboxylates is dominated by formation of multinuclear tin assemblies, we found that under catalytically relevant conditions only monomericn-BuSn(OAc)3and dimeric (n-BuSnOAc2OEt)2are present. Density functional theory (DFT) calculations provide support for a mononuclear mechanism, wheren-BuSn(OAc)3and dimeric (n-BuSnOAc2OEt)2are regarded as off-cycle species, and suggest that carbon-oxygen bond breaking is the rate-determining step.

Titanium-catalyzed esterification reactions: beyond Lewis acidity

Esterification is a key reaction and is used in many synthetic and industrial processes, yet the detailed mechanism of operation of often-used (Lewis acid) catalysts is unknown and subject of little research. Here, we report on mechanistic studies of a titanium aminotriphenolate catalyst, using stoichiometric and catalytic reactions combined with kinetic data and density functional theory (DFT) calculations. While often only the Lewis acidity of the Ti-center is taken into account, we found that the amphoteric nature of this catalyst, combining this Lewis acidity with Br?nsted basicity of a Ti-bound and in situ formed carboxylate group, is crucial for catalytic activity. Furthermore, hydrogen bonding interactions are essential to pre-organize substrates and to stabilize various intermediates and transition states and thus enhancing the overall catalytic reaction. These findings are not only applicable to this class of catalysts, but could be important for many other esterification catalysts.

LiHMDS: Facile, highly efficient and metal-free transesterification under solvent-free condition

Transesterification is one of the important organic reactions employed in numerous industrial as well as laboratory applications for the synthesis of various esters. Herein, we report a rapid, highly efficient, and transition metal-free transesterification reaction in the presence of LiHMDS under solvent-free conditions. The transesterification reaction was carried out with three different benzoate esters and a wide range of primary and secondary alcohols (from C3-C18) in good to excellent yields (45 examples). By considering the commercial role of esters, this method will be promising for the facile synthesis of esters in industry-relevant applications.

Electrochemical esterification via oxidative coupling of aldehydes and alcohols

An electrolytic method for the direct oxidative coupling of aldehydes with alcohols to produce esters is described. Our method involves anodic oxidation in presence of TBAF as supporting electrolyte in an undivided electrochemical cell equipped with graphite electrodes. This method successfully couples a wide range of alcohols to benzaldehydes with yields ranging from 70 to 90%. The protocol is easy to perform at a constant voltage conditions and offers a sustainable alternative over conventional methods.

Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids Using α,α-Dichlorodiphenylmethane

A new method for chlorination of alcohols and carboxylic acids, using α,α-dichlorodiphenylmethane as the chlorinating agent and FeCl3 as the catalyst, was developed. The method enables conversions of various alcohols and carboxylic acids to their corresponding alkyl and acyl chlorides in high yields under mild conditions. Particulary interesting is the observation that the respective alkyl bromides and iodides can be generated from alcohols when either LiBr or LiI are present in the reaction mixtures.

Zirconocene-catalyzed direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio under solvent-free conditions

A highly efficient way for the direct (trans)esterification of acyl acids (esters) and alcohols in a strict 1:1 ratio using a zirconocene complex (1, 1 mol%), a strong Lewis acid of good water tolerance, as a catalyst under solvent-free conditions has been developed. A wide range of acid and alcohol (esters) substrates undergo (trans)esterification to produce carboxylic ester motifs in moderate to good or excellent yields with good functional tolerance, such as that towards C-Br as well as CC and CC bonds. And complex 1 can be recycled six times without showing a significant decline in catalytic efficiency. It was demonstrated that cyclandelate, which is used to treat high blood pressure as well as heart and blood-vessel diseases, can be directly synthesized on a gram scale with 81% yield (6.70 g) using complex 1.

Pd/C-Catalyzed Carbonylative Esterification of Aryl Halides with Alcohols by Using Oxiranes as CO Sources

A carbonylative esterification reaction between aryl bromides and alcohols, promoted by Pd/C and NaF in the presence of oxiranes, has been developed. In this process, oxiranes serve as sources of carbon monoxide by their conversion to aldehydes through a palladium-promoted Meinwald rearrangement pathway. Intramolecular versions of this process serve as methods for the synthesis of lactones and phthalimides. CO gas free! A carbonylative esterification reaction between aryl bromides and alcohols, promoted by Pd/C and NaF in the presence of oxiranes, has been developed. In this process, oxiranes serve as sources of carbon monoxide by their conversion to aldehydes through a palladium-promoted Meinwald rearrangement pathway (see scheme).

Metal-Free Oxidative Cross Esterification of Alcohols via Acyl Chloride Formation

A novel metal-free oxidative cross esterification of alcohols has been achieved using trichloroisocyanuric acid as an oxidant. The alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with primary and secondary aliphatic, benzylic and allylic alcohols and phenols. A wide variety of esters was obtained in satisfactory yields.

Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA

Aromatic and aliphatic aldehydes are simply converted into esters by an efficient oxidative esterification carried out under mild conditions. The aldehydes are converted in situ into their corresponding acyl chlorides, which are then reacted with primary and secondary aliphatic, benzylic, allylic, and propargylic alcohols and phenols. A variety of esters are obtained in high yields.

Copper-catalyzed cross-coupling of thiols, alcohols, and oxygen for the synthesis of esters

Copper-catalyzed, one-pot, three-component coupling reactions using thiols, alcohols, and oxygen to form a variety of esters in good yields were studied. In the presence of easily oxidized benzylic and allylic alcohols, thiols were selectively oxidized to form thionoesters, which underwent facile S/O exchange to afford esters. Thiols may be used as an alternative benzoyl source under mild aerobic conditions.