93-89-0

Basic information

• Product Name: Ethyl benzoate
• Synonyms: ETHYL BENZOATE FOR SYNTHESIS 1 L;ETHYL BENZOATE FOR SYNTHESIS 250 ML;Ethyl benzoate, Standard for GC,>99.5%(GC);Ethyl benzoate Vetec(TM) reagent grade, 98%;ETHYL BENZENECARBOXYLATE;ETHYL BENZOATE;BENZOIC ACID ETHYL ESTER;BENZOIC ETHER
• CAS NO: 93-89-0
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 202-284-3
• Product Categories: CARBOXYLICESTER;Organics;C8 to C9;Carbonyl Compounds;Esters;Certified Natural ProductsFlavors and Fragrances;E-F;Alphabetical Listings;Flavors and Fragrances;organic chemical
• Mol File: 93-89-0.mol
• Article Data: 691

Chemical Properties

• Melting Point: -34 °C
• Boiling Point: 212 °C(lit.)
• Flash Point: 184 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.045 g/mL at 25 °C(lit.)
• Vapor Density: 5.17 (vs air)
• Vapor Pressure: 1 mm Hg ( 44 °C)
• Refractive Index: n20/D 1.504(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.5g/l
• Relative Polarity: 0.228
• Explosive Limit: 1%(V)
• Water Solubility: INSOLUBLE
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,3766
• BRN: 1908172
• CAS DataBase Reference: Ethyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl benzoate(93-89-0)
• EPA Substance Registry System: Ethyl benzoate(93-89-0)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 24/25-61
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 1
• RTECS: DH0200000
• TSCA: Yes
• Hazardous Substances Data: 93-89-0(Hazardous Substances Data)

Usage

Description

Ethyl benzoate, C9H10O2, is the ester formed by the condensation of benzoic acid and ethanol. It is a colorless liquid that is almost insoluble in water, but miscible with most organic solvents. As with many volatile esters, ethyl benzoate has a pleasant odor which could be described similar to wintergreen mint. It is a component of some artificial fruit flavors.

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

• 110-89-4 piperidine 
• 64-17-5 ethanol 
• 21299-15-0 diethyl 2,4-dibenzoylpentanedioate 
• 614-33-5 glyceryl tribenzoate 
• 141-52-6 sodium ethanolate 
• 455-32-3 benzoyl fluoride 
• 60-29-7 diethyl ether 
• 541-41-3 chloroformic acid ethyl ester 
• 532-32-1 sodium benzoate 
• 65-85-0 benzoic acid 
• 78-07-9 ethyltriethoxy silane 
• 98-88-4 benzoyl chloride 
• 623-81-4 diethyl sulphite 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 776-75-0 N-benzoylpiperidine 
• 2905-56-8 N-Benzylpiperidine 
• 4476-13-5 N-[2-(4-morpholinyl)ethyl]benzamide 
• 1620-53-7 1-phenyl-2-pyridin-2-ylethanone 
• 18103-77-0 (4-methylpyridin-2-yl)(phenyl)methanone 
• 21034-21-9 α-benzoyl-γ-butyrolactone 
• 22125-05-9 Phenyl-di-[3]pyridyl-methanol 
• 55153-58-7 1,3,5-triphenylpenta-1,4-diyn-3-ol 
• 10471-74-6 1-phenyl-3-(thiophen-2-yl)propane-1,3-dione 
• 91-01-0 1,1-Diphenylmethanol 
• 7543-20-6 1-Phenyl-2-(4-quinolyl)ethanone 
• 2315-68-6 propyl benzoate 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 1565-71-5 3-phenylpentan-3-ol 

Relevant articles and documents

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.

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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.

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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

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.

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.