93-89-0

Usage

Chemical Properties

Ethyl benzoate is a colourless liquid that has a somewhat fruity odor similar to ylang-ylang, but milder than methyl benzoate. Soluble in ethanol, ethyl ether, petroleum ether, propylene glycol, mineral oil and most non-volatile oils, insoluble in water and glycerin.

Occurrence

Reported found in volatiles from hard, mature peaches, pineapple and currant. Also reported found in apple juice, banana, guava, cranberry, raspberry, sweet cherry, Parmesan cheese, butter, milk, white wine, red wine, cider, whiskies, cocoa, black tea, fresh plum, apple brandy, cherry brandy, Bourbon vanilla, naranjilla fruit, ceriman or pinanona, pimento berry, olive and passion fruit.

Uses

Different sources of media describe the Uses of 93-89-0 differently. You can refer to the following data:
1. Ethyl Benzoate acts as an aroma and flavour compound due to the volatile ester group in its structure. In perfumery under the name Essence de Niobe; in manufacture of Peau d'Espagne; artificial fruit essence.
2. Ethyl benzoate is used as a perfume scent. It acts as a food flavoring agent. It is an active component of artificial fruit flavors. Further, it is used in cosmetics and personal care products as fragrance ingredients and preservatives.

Preparation

By esterification of ethyl alcohol and benzoic acid in the presence of anhydrous aluminum sulfate and a trace of sulfuric acid; by transesterification of methyl benzoate with ethanol in the presence of potassium ethylate

Definition

ChEBI: Ethyl benzoate is a benzoate ester obtained by condensation of benzoic acid and ethanol. It is a volatile oil component found in ripe kiwifruit, cranberry juice, and palm kernel oil. It has a role as a flavouring agent, a fragrance and a volatile oil component. It is a benzoate ester and an ethyl ester.

Aroma threshold values

Detection: 100 ppb; recognition: 150 ppb

Taste threshold values

Taste characteristics at 30 ppm: sweet, medicinal, green, minty, fruity, birch beer and wintergreen-like.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1703, 1960 DOI: 10.1021/jo01080a004Synthetic Communications, 20, p. 2267, 1990 DOI: 10.1080/00397919008053167Tetrahedron Letters, 22, p. 1509, 1981 DOI: 10.1016/S0040-4039(01)90363-6

General Description

Natural occurrence: Feijoa, guava, plum, raspberry, rum, strawberry, Virginia tobacco.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion. Mildly toxic by skin contact. A skin and eye irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS

InChI:InChI=1/C9H10O2/c1-2-11-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3

Upstream product

• 109-99-9 tetrahydrofuran 
• 127-09-3 sodium acetate 
• 2028-79-7 4-(ethoxycarbonyl)benzenediazonium chloride 
• 110-89-4 piperidine 
• 64-17-5 ethanol 
• 21299-15-0 diethyl 2,4-dibenzoylpentanedioate 
• 110-86-1 pyridine 
• 143-33-9 sodium cyanide 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 93-58-3 benzoic acid methyl ester 
• 60-29-7 diethyl ether 
• 141-52-6 sodium ethanolate 
• 613-90-1 benzoyl cyanide 
• 451-40-1 phenyl benzyl ketone 

Downstream Products

• 776-75-0 N-benzoylpiperidine 
• 2905-56-8 N-Benzylpiperidine 
• 4476-13-5 N-[2-(4-morpholinyl)ethyl]benzamide 
• 18103-77-0 (4-methylpyridin-2-yl)(phenyl)methanone 
• 21034-21-9 α-benzoyl-γ-butyrolactone 
• 22125-05-9 Phenyl-di-[3]pyridyl-methanol 
• 55-21-0 benzamide 
• 85997-32-6 4-dimethylamino-1-phenyl-but-2-yn-1-one 
• 55153-58-7 1,3,5-triphenylpenta-1,4-diyn-3-ol 
• 1620-53-7 1-phenyl-2-pyridin-2-ylethanone 
• 10471-74-6 1-phenyl-3-(thiophen-2-yl)propane-1,3-dione 
• 1565-71-5 3-phenylpentan-3-ol 
• 91-01-0 1,1-Diphenylmethanol 
• 93-97-0 benzoic acid anhydride 

Relevant academic research and scientific papers

Ester Interchange Reaction Catalyzed by Lanthanoid Tri-2-propoxides

Lanthanoid tri-2-propoxides (i)3>n Ln = La, Nd, Gd, Yb) are active catalysts for the interchange reaction of the alkoxyl groups between two kinds of esters.The La catalyst is the most active among them, and the activity is higher in nonpolar solvents than in polar ones.The La catalyst is applicable to the ring-opening polymerization of 6-hexanolide.

Enantioselective sulfenylation of α-nitroesters catalyzed by diarylprolinols

The organocatalytic sulfenylation of α-nitroesters mediated by diaryl-l-prolinols was developed. A range of α-sulfenylated α-nitroesters were obtained in good yields with moderate to good enantioselectivities.

7,8,9-trimethyl-1-phenyl-3H-pyrrolo[2,1-d][1,2,5]triazepin-4(5H)-one. Synthesis and reactions

A strategy was developed for the synthesis of 7,8,9-trimethyl-1-phenyl-3H-pyrrolo[2,1-d][1,2,5]-triazepin-4(5H)-one, reactions of its functionalization at the С4 atom and aza rings fusion at the С4?N3 bond were explored. The formation mechanism of the pyrrolo-1,2,5-triazepinone scaffold was suggested.

Production of Copolyester Monomers from Plant-Based Acrylate and Acetaldehyde

PCTA is an important copolyester that has been widely used in our daily necessities. Currently, its monomers are industrially produced from petroleum-derived xylene. To reduce the reliance on fossil energy, we herein disclose an alternative route to acces

A one-pot and two-stage Baeyer-Villiger reaction using 2,2′-diperoxyphenic acid under biomolecule-compatible conditions?

An efficient oxidant named 2,2′-diperoxyphenic acid was newly developed, and it exhibited high stability as revealed by thermogravimetric analysis (TGA) coupled with differential scanning calorimetry (DSC). On applying this reagent in the Baeyer-Villiger oxidation, the reaction featured a markedly broad substrate scope and good functional group tolerance, giving rise to the corresponding products in good to excellent yields. Particularly, in the case of pure water or 1× Phosphate Buffered Saline (1× PBS) serving as the solvent, the protocol could work well, resulting in yields ranging from 81% to 98%. Moreover, the catalytic asymmetric version of the BV reaction was explored as well, affording the corresponding products in good yields and medium ee. Remarkably, the corresponding biological compatibility and greenness assessment indicated that this reagent had favorable application prospects in the biomedical and green manufacturing fields. Meanwhile, mechanistic studies including 18O isotope effect experiments and DFT computations suggested that this reaction followed the generally accepted mechanism of BV oxidation.

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.

Copper-mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols

A simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen, which produces a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, which allows the oxygenation of C-H bond, cleavage of inert C-C bond, and formation of C-O bond in one pot without the assistance of any of the acids, bases, ligands, and so on. The reaction provides a simple, direct, and efficient protocol towards functionalized esters, especially aryl benzoates, from readily available starting materials.

Metal- and Solvent-Free Transesterification and Aldol Condensation Reactions by a Homogenous Recyclable Basic Ionic Liquid Based on the 1,3,5-Triazine Framework

A new recyclable basic ionic liquid was introduced as an efficient catalyst for aldol condensation and transesterification reactions under environmentally friendly conditions. The catalyst was prepared based on methyl imidazolium moieties bearing hydroxide counter anions via the Hofmann elimination on a 1,3,5-triazine framework. The ionic liquid with two functionalities including anion stabilizer and high basicity, was used as an efficient catalyst for aldol condensation as well as transesterification reaction of a variety of alkyl benzoates. All reactions were performed in the absence of any external reagent, co-catalyst, or solvent, in line with environmental protection. The kinetics isotope effect (KIE) was conducted for the transesterification reaction to elucidate the mechanism and rate determining step (RDS). It worth noted that, the homogeneous catalyst could be recycled from the reaction mixture and reused for several consecutive runs with insignificant drop of basicity and conversion.

Experimental Evidence of syn H-N-Fe-H Configurational Requirement for Iron-Based Bifunctional Hydrogenation Catalysts

Iron hydrides supported by a pincer ligand of the type HN(CH2CH2PR2)2 (RPNHP) are versatile hydrogenation catalysts. Previous efforts have focused on using CO as an additional ligand to stabilize the hydride species. In this work, CO is replaced with isocyanide ligands, leading to the isolation of two different types of iron hydride complexes: (RPNHP)FeH(CNR′)(BH4) (R = iPr, R′ = 2,6-Me2C6H3, tBu; R = Cy, R′ = 2,6-Me2C6H3) and [(iPrPNHP)FeH(CNtBu)2]X (X = BPh4, Br, or a mixture of Br and BH4). The neutral iron hydrides are capable of catalyzing the hydrogenation of PhCO2CH2Ph to PhCH2OH, although the activity is lower than for (iPrPNHP)FeH(CO)(BH4). The cationic iron hydrides are active hydrogenation catalysts only for more reactive carbonyl substrates such as PhCHO, and only when the NH and FeH hydrogens are syn to each other. The cationic species and their synthetic precursors [(iPrPNHP)FeBr(CNtBu)2]X (X = BPh4, Br) can have different configurations for the isocyanide ligands (cis or trans) and the H-N-Fe-H(Br) unit (syn or anti). Unlike tetraphenylborate, the bromide counterion participates in a hydrogen-bonding interaction with the NH group, which influences the relative stability of the cis,anti and cis,syn isomers. These structural differences have been elucidated by X-ray crystallography, and the geometric isomerization processes have been studied by NMR spectroscopy.

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.