122-70-3

Basic information

• Product Name: 2-PHENYLETHYL PROPIONATE
• Synonyms: FEMA 2867;FEMA 3867;BETA PHENYL ETHYL PROPIONATE;B-PHENYLETHYL PROPIONATE;2-PHENYLETHYL PROPIONATE;PHENETHYL PROPIONATE;PHENYL ETHYL PROPIONATE;2-Phenethyl propionate
• CAS NO: 122-70-3
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• EINECS: 203-013-1
• Mol File: 122-70-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 245 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless liquid
• Density: 1.007 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0199mmHg at 25°C
• Refractive Index: n20/D 1.493(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 136mg/L at 25℃
• CAS DataBase Reference: 2-PHENYLETHYL PROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYLETHYL PROPIONATE(122-70-3)
• EPA Substance Registry System: 2-PHENYLETHYL PROPIONATE(122-70-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36-24/25
• WGK Germany: 2
• RTECS: AJ3255000
• TSCA: Yes
• Hazardous Substances Data: 122-70-3(Hazardous Substances Data)

Usage

Description

2-PHENYLETHYL PROPIONATE, also known as Phenethyl propionate, is a naturally occurring organic compound that can be found in various food products and beverages. It is characterized by its clear colorless liquid appearance and a very sweet odor reminiscent of red rose with a fruity undertone. The compound has a honey-like, warm, sweet raspberry, and strawberry-like flavor, making it a valuable ingredient in the flavor and fragrance industry.

Uses

Used in Flavor and Fragrance Industry:
2-PHENYLETHYL PROPIONATE is used as a flavoring agent for its sweet raspberry and strawberry-like flavor, adding a pleasant taste to various food products and beverages. It is also used as a fragrance ingredient for its red rose and fruity undertone, contributing to the creation of various scents in the perfume industry.
Used in Commercial Wines:
2-PHENYLETHYL PROPIONATE is used as a flavoring agent in commercial wines, enhancing their taste and aroma by providing a sweet raspberry and strawberry-like flavor.
Used in Food Industry:
2-PHENYLETHYL PROPIONATE is used as a flavoring agent in the food industry, adding a warm, sweet raspberry and strawberry-like flavor to various products, such as candies, baked goods, and other confectioneries.
Used in Beverage Industry:
2-PHENYLETHYL PROPIONATE is used as a flavoring agent in the beverage industry, particularly in the production of fruit-flavored drinks, where its sweet raspberry and strawberry-like flavor can enhance the overall taste and appeal of the product.

Preparation

By esterification of phenyl alcohol with propionic acid.

Safety Profile

Low toxicity by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C11H14O2/c1-2-11(12)13-9-8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

Synthetic route

phenethyl 2-chloropropanoate → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol at 100℃; Schlenk technique; Inert atmosphere;	67%
With [RhCl2(p-cymene)]2; cesium acetate In isopropyl alcohol at 20 - 100℃; for 20h; Inert atmosphere;	67%
Multi-step reaction with 2 steps 1: sodium iodide / acetone / 50 °C 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol / 100 °C / Schlenk technique; Inert atmosphere View Scheme

2-phenylethanol (60-12-8) + propionic acid (802294-64-0) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With pyridine; N-Bromosuccinimide; triphenylphosphine In dichloromethane; pentane for 2h; Ambient temperature;	93%
With ion-exchange resin KU-2-8 In benzene at 80 - 85℃;	92%
With dmap; triphenylphosphine; iodosodilactone In chloroform for 2h; Reflux;	92%

propanoic acid methyl ester (554-12-1) + 2-phenylethanol (60-12-8) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With zirconocene bis(perfluorooctanesulfonate) trihydrate*(tetrahydrofuran) In neat (no solvent) at 65℃; for 6h; Sealed tube; Green chemistry; chemoselective reaction;	90%

2-phenylethanol (60-12-8) + propionic acid anhydride (123-62-6) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
zinc(II) perchlorate at 20℃; for 1.25h;	99%
With dmap for 0.05h; Irradiation; microwave;	95%

propionic acid (802294-64-0) + 1-phenyl-2-bromoethane (103-63-9) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With tetradecyl(trihexyl)phosphonium bistriflamide; N-ethyl-N,N-diisopropylamine at 75℃;	98%
With tetradecyl(trihexyl)phosphonium bistriflimide at 75℃; for 6h;	98%

2-phenylethanol (60-12-8) + propionaldehyde (123-38-6) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; bromine; sodium hydrogencarbonate In dichloromethane; water	89%

diethyl (1-oxopropyl)phosphonate (1523-68-8) + 2-phenylethanol (60-12-8) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.166667h; Ambient temperature;	70%

2-phenylethanol (60-12-8) + Ethyl propionate (105-37-3) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
Stage #1: 2-phenylethanol With bis(cyclopentadienyl)titanium dichloride; manganese; diiodomethane In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere; Stage #2: Ethyl propionate In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;
With recombinant acyltransferase from Mycobacterium smegmatis In aq. phosphate buffer at 25℃; for 0.5h; pH=8; Concentration; Green chemistry; Enzymatic reaction;

phenethyl 2-iodopropanoate → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol at 100℃; Schlenk technique; Inert atmosphere;	71%

2-phenylethanol (60-12-8) + ZnCl2 → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / 3 h / Ambient temperature 2: 2-propanol, di-tert-butyl hyponitrite / 5 h / 60 °C / average chain length radical chain View Scheme

2-phenylethanol (60-12-8) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 - 20 °C 2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol / 100 °C / Schlenk technique; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 0 - 20 °C 2: sodium iodide / acetone / 50 °C 3: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol / 100 °C / Schlenk technique; Inert atmosphere View Scheme

2-bromophenylethyl alcohol (1074-16-4) → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; isopropyl alcohol; potassium tert-butylate / 100 °C / Schlenk technique; Inert atmosphere 2: pyridine / dichloromethane / 0 - 20 °C 3: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol / 100 °C / Schlenk technique; Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; isopropyl alcohol; potassium tert-butylate / 100 °C / Schlenk technique; Inert atmosphere 2: pyridine / dichloromethane / 0 - 20 °C 3: sodium iodide / acetone / 50 °C 4: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cesium acetate; isopropyl alcohol / 100 °C / Schlenk technique; Inert atmosphere View Scheme

benzene (71-43-2) + aqueous KOH → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: anhydrous aluminum chloride / 4 h / 6 - 7 °C 1.2: 90 percent / water 2.1: 92 percent / ion-exchange resin KU-2-8 / benzene / 80 - 85 °C View Scheme

2-Bromo-propionic acid phenethyl ester → 2-phenethyl propanoate (122-70-3)

Conditions	Yield
With 1,2,2,6,6-pentamethylpiperidine; trans-di-O-tert-butyl hyponitrite In acetonitrile at 60℃; for 5h;
With isopropyl alcohol; trans-di-O-tert-butyl hyponitrite at 60℃; for 5h; average chain length radical chain;

methanol (67-56-1) + 2-phenethyl propanoate (122-70-3) → propanoic acid methyl ester (554-12-1) + 2-phenylethanol (60-12-8)

Conditions	Yield
[t-Bu2SnOH(Cl)]2 at 30℃; for 3.5h;	A n/a B 65 % Chromat.

Upstream product

• 1523-68-8 diethyl (1-oxopropyl)phosphonate 
• 60-12-8 2-phenylethanol 
• 123-38-6 propionaldehyde 
• 802294-64-0 propionic acid 
• 123-62-6 propionic acid anhydride 
• 103-63-9 1-phenyl-2-bromoethane 
• 71-43-2 benzene 
• 105-37-3 Ethyl propionate 
• 1074-16-4 2-bromophenylethyl alcohol 
• 32364-83-3 phenethyl 2-chloropropanoate 
• 554-12-1 propanoic acid methyl ester 

Downstream Products

• 554-12-1 propanoic acid methyl ester 
• 60-12-8 2-phenylethanol 

Relevant articles and documents

Efficient Enzymatic Preparation of Flavor Esters in Water

A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.

Transfer Hydro-dehalogenation of Organic Halides Catalyzed by Ruthenium(II) Complex

A simple and efficient Ru(II)-catalyzed transfer hydro-dehalogenation of organic halides using 2-propanol solvent as the hydride source was reported. This methodology is applicable for hydro-dehalogenation of a variety of aromatic halides and α-haloesters and amides without additional ligand, and quantitative yields were achieved in many cases. The potential synthetic application of this method was demonstrated by efficient gram-scale transformation with catalyst loading as low as 0.5 mol %.

Efficient O-Acylation of Alcohols and Phenol Using Cp2TiCl as a Reaction Promoter

A method has been developed for the conversion of primary, secondary, and tertiary alcohols, and phenol, into the corresponding esters at room temperature. The method uses a titanium(III) species generated from a substoichiometric amount of titanocene dichloride together with manganese(0) as a reductant, as well as methylene diiodide. It involves a transesterification from an ethyl ester, or a reaction with an acyl chloride. A radical mechanism is proposed for these transformations.