122-63-4

Basic information

• Product Name: Benzyl propionate
• Synonyms: Benzylpropionat;enzyl n-propionate;Propanoicacid,phenylmethylester;propanoicacidphenylmethylester;BENZYL N-PROPANOATE;BENZYL PROPANOATE;BENZYL PROPIONATE;FEMA 2150
• CAS NO: 122-63-4
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 204-559-3
• Product Categories: A-BFlavors and Fragrances;Alphabetical Listings;Certified Natural Products;Flavors and Fragrances;A-B
• Mol File: 122-63-4.mol
• Article Data: 90

Chemical Properties

• Melting Point: 221-223°C
• Boiling Point: 222 °C(lit.)
• Flash Point: 205 °F
• Appearance: Clear colourless liquid
• Density: 1.03 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.105mmHg at 25°C
• Refractive Index: n20/D 1.497(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 1000g/L in organic solvents at 20 ℃
• PKA: 0[at 20 ℃]
• Water Solubility: 100-742mg/L at 20-25℃
• BRN: 2046122
• CAS DataBase Reference: Benzyl propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl propionate(122-63-4)
• EPA Substance Registry System: Benzyl propionate(122-63-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: UA2537603
• TSCA: Yes
• Hazardous Substances Data: 122-63-4(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 122-63-4 differently. You can refer to the following data:
1. CLEAR COLOURLESS LIQUID
2. Benzyl propionate is a liquid with a sweet, fruity odor, which is used in perfumery for floral, fruity notes and in fruit flavor compositions.
3. Benzyl propionate has a sweet, fruity-floral odor and a peach-, apricot-like taste.

Occurrence

Reported found in strawberry and melon.

Uses

Benzyl Propionate is a flavoring agent which is liquid, colorless and has a sweet, fruity odor. it is soluble in most fixed oils and alcohol, slightly soluble in propylene glycol, and insoluble in glycerin.

Preparation

By esterification of benzyl alcohol with propionic acid.

Taste threshold values

Taste characteristics at 15 ppm: fruity, sweet, green and powdery with a ripe berry nuance.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 5678, 1990 DOI: 10.1021/jo00309a007Synthetic Communications, 25, p. 2435, 1995 DOI: 10.1080/00397919508015447Synthesis, p. 853, 1990 DOI: 10.1055/s-1990-27034

Biochem/physiol Actions

Taste at 30 ppm

InChI:InChI=1/C10H12O2/c1-2-10(11)12-8-9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

Synthetic route

propionic acid anhydride (123-62-6) + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With erbium(III) chloride at 50℃; for 1.5h;	99%
With tris(pentafluorophenyl)borate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry;	98%
With decamolybdodivanadogermanic acid nanoparticles at 24.84℃; for 0.166667h; Neat (no solvent);	91%

propionic acid (802294-64-0) + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With dmap; 4-methyl-benzoyl chloride; triethylamine In tetrahydrofuran at 20℃; for 1h;	98%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane for 1h; Ambient temperature;	95%
ammonium cerium(IV) nitrate In chloroform at 55 - 60℃;	95%

3-(2-benzyloxycarbonyl-ethyldisulfanyl)-propionic acid benzyl ester (952423-86-8) → benzyl proprionate (122-63-4)

Conditions	Yield
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 20℃; UV-irradiation;	89%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;	89%

benzylacrylate (2495-35-4) → benzyl proprionate (122-63-4)

Conditions	Yield
With hydrogen; palladium nanoparticles In toluene at 20℃; for 24h;	99%
With hydrogen; PdCl,N In methanol at 20℃; for 4h; Product distribution; Further Variations:; Catalysts; Solvents; time;	97%
With sodium tetrahydroborate; copper(ll) sulfate pentahydrate; cobalt(II) chloride hexahydrate In methanol at 20℃; for 0.166667h;	94%

benzyl 2-sulfanylpropanoate (16850-01-4, 1192480-83-3) → benzyl proprionate (122-63-4)

Conditions	Yield
With di-tert-butyl peroxide; triethyl phosphite In tetrahydrofuran	95%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;	95%

benzyl 2-mercaptopropanoate (16850-00-3) → benzyl proprionate (122-63-4)

Conditions	Yield
With di-tert-butyl peroxide; triethyl phosphite In ethyl acetate	93%
With di-tert-butyl peroxide; triethyl phosphite In acetonitrile at 25℃; for 6h; Irradiation;	93%

1-phenyl-2-buten-1-ol (52755-38-1, 52755-39-2, 87246-95-5, 92075-81-5, 100017-30-9, 115793-56-1, 146566-32-7, 3347-57-7) + toluene (108-88-3) → benzyl proprionate (122-63-4) + benzoic acid benzyl ester (120-51-4)

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 80℃; for 24h; Sealed tube;	A 68% B 55%

ethylmagnesium bromide (925-90-6) + O-benzyl S-(pyridin-2-yl)carbonothioate (91285-94-8) → benzyl proprionate (122-63-4)

Conditions	Yield
In tetrahydrofuran at 0 - 50℃; for 1h; Temperature; Grignard Reaction; Inert atmosphere;	80%

α,α-dipropionoxytoluene (55696-47-4) + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With potassium carbonate at 90℃; for 16h;	94%

phenyl(propionyloxy)methyl pivalate + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With potassium carbonate at 90℃; for 16h;	94%

benzyl prop-2-ynoate (14447-01-9) → benzyl proprionate (122-63-4)

Conditions	Yield
With hydrogen In methanol at 25℃; for 6h;	97%
With hydrogen In methanol at 25℃; under 760.051 Torr; for 9h; Green chemistry; chemoselective reaction;	78%

sodium proprionate (137-40-6) + benzyl chloride (100-44-7) → benzyl proprionate (122-63-4)

Conditions	Yield
With zirconium (benzyldiethylammoniomethylphosphonate chloride) phosphate In water; toluene at 88℃; for 16h;	81.1%
With water at 110 - 115℃;
With graphene oxide supported quaternary ammonium salt at 120℃; for 7h;

benzyloxydiphenylphosphine (53772-44-4) + propionic acid (802294-64-0) → benzyl proprionate (122-63-4)

Conditions	Yield
With 2,6-dimethyl-1,4-benzoquinone In dichloromethane at 20℃; for 0.5h;	89%

propionaldehyde (123-38-6) + toluene (108-88-3) → benzyl proprionate (122-63-4)

Conditions	Yield
With tert.-butylhydroperoxide In decane at 80℃; for 5h; Inert atmosphere;	92%

ethane (74-84-0) + carbon monoxide (201230-82-2) + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With di-tert-butyl peroxide; α,α,α-trifluorotoluene; triphenylphosphine; palladium dichloride In 1,2-dichloro-ethane at 110℃; under 3800.26 Torr; for 10h; Autoclave;	61%
With di-tert-butyl peroxide In 1,2-dichloro-ethane at 120℃; under 15001.5 Torr; for 10h; Autoclave;	30%

benzyl 2-bromopropionate (3017-53-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With DMBI In tetrahydrofuran for 9h; Heating;	90%
Multi-step reaction with 2 steps 1: potassium iodide / acetone / Inert atmosphere; Reflux 2: H2B(μ-3,5-dimethylpyrazole)2BH2; 2,2'-azobis(isobutyronitrile) / toluene / 2 h / 85 °C / Inert atmosphere View Scheme

benzyl 2-chloropropanoate (81577-34-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With DMBI In 1,4-dioxane for 11h; Heating;	93%
With indium; sodium dodecyl-sulfate at 50℃; for 6h;	88 % Spectr.

tetrahydro-2-(benzyloxy)-2H-pyran (1927-62-4) + propionyl chloride (79-03-8) → benzyl proprionate (122-63-4)

Conditions	Yield
With montmorillonite K-10 In chloroform at 20℃; for 0.5h;	87%

benzyloxy-trimethylsilane (14642-79-6) + propionyl chloride (79-03-8) → benzyl proprionate (122-63-4)

Conditions	Yield
With montmorillonite K-10 In chloroform at 20℃; for 0.3h;	88%

vinyl propionate (105-38-4) + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With diethylzinc In hexane; toluene at 20℃; for 2.5h;	90%

propionic acid (802294-64-0) + benzylamine (100-46-9) → benzyl proprionate (122-63-4)

Conditions	Yield
With sodium nitrite In water at 0 - 20℃; for 0.333333h;	82%

benzyl 2-iodopropanoate (90891-07-9) → benzyl proprionate (122-63-4)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); H2B(μ-3,5-dimethylpyrazole)2BH2 In toluene at 85℃; for 2h; Inert atmosphere;	54%

benzyl ethyl ketone (1007-32-5) → benzyl proprionate (122-63-4)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 6.5h; Baeyer-Villiger oxidation;	70%
With 3-chloro-benzenecarboperoxoic acid; Mg10Al2(OH)24CO3 In 1,2-dichloro-ethane at 40℃; for 5h; Product distribution; with/without catalyst;	66 % Chromat.
With 3-chloro-benzenecarboperoxoic acid; Mg10Al2(OH)24CO3 In 1,2-dichloro-ethane at 40℃; for 5h;	66 % Chromat.
With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid In dichloromethane at 0 - 24℃; for 24h; Baeyer-Villiger Ketone Oxidation;
With glucose dehydrogenase; D-glucose; LGY1-248-D3; oxygen; nicotinamide adenine dinucleotide phosphate In aq. buffer at 30℃; for 15h; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction;

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + propionic acid (802294-64-0) → benzyl proprionate (122-63-4)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane; cyclohexane for 24h; Ambient temperature;	77%

propionyl chloride (79-03-8) + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With zinc In benzene for 0.166667h; Esterification;	85%

benzyl bromide (100-39-0) + propionic acid (802294-64-0) → benzyl proprionate (122-63-4)

Conditions	Yield
In neat (no solvent) at 20℃; for 1h;	78%

Ethyl propionate (105-37-3) + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature;	58%
With recombinant acyltransferase from Mycobacterium smegmatis In aq. phosphate buffer at 25℃; for 0.5h; pH=8; Concentration; Green chemistry; Enzymatic reaction;

diethyl 1-propionyl-1,4-dihydropyridine-3,5-dicarboxylate + benzyl alcohol (100-51-6) → benzyl proprionate (122-63-4)

Conditions	Yield
Stage #1: diethyl 1-propionyl-1,4-dihydropyridine-3,5-dicarboxylate With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 0.5h; Stage #2: benzyl alcohol With dmap In dichloromethane for 22.5h;	48%

α,α-dipropionoxytoluene (55696-47-4) → benzyl proprionate (122-63-4)

Conditions	Yield
With zinc In acetonitrile at 70℃; for 24h;

benzyl alcohol (100-51-6) + 1-cyclopentyl-hexanoic acid (6) → benzyl proprionate (122-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / Et3N / diethyl ether / 2 h / Ambient temperature 2: H2 / 6H11)3(Py)>PF6 / methanol / 17 h / 760 Torr / Ambient temperature View Scheme

benzyl proprionate (122-63-4) + phenethylamine (64-04-0) → N-phenethylpropionamide (6283-04-1) + N-benzyl-2-phenylethylamine (3647-71-0)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In neat (no solvent) at 115℃; for 24h; Inert atmosphere; Glovebox; Green chemistry;	A 98% B 67%

benzyl proprionate (122-63-4) → 1,1-dideuteriopropanol (40422-04-6)

Conditions	Yield
With lithium aluminium deuteride In diethyl ether	93%
With lithium aluminium deuteride In diethyl ether for 5h; Heating;

benzyl proprionate (122-63-4) + isobutyraldehyde (78-84-2) → (2R,3S)-3-Hydroxy-2,4-dimethyl-pentanoic acid benzyl ester

Conditions	Yield
Stage #1: benzyl proprionate With diethyl-cyclohexyl-amine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane Stage #2: isobutyraldehyde at -78 - 0℃; for 2h; Further stages.;	88%

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9) + benzyl proprionate (122-63-4) → benzyl 2-methyl-3-oxo-pentanoate (162662-03-5) + benzyl 2-(2'-hydroxytetrahydropyran-2'-yl)propionate

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Product distribution; Mechanism; various reaction conditions;	A 84% B 8%
With n-butyllithium In tetrahydrofuran; hexane 1.) 0 deg C, 45 min, 2.) -78 deg C, 3 h;	A 84% B 8%

methyl 2-(benzyloxy)acetate (31600-43-8) + benzyl proprionate (122-63-4) → benzyl 4-(benzyloxy)-2-methyl-3-oxobutanoate (214333-77-4)

Conditions	Yield
With lithium diisopropyl amide	80%

benzyl proprionate (122-63-4) + isobutyraldehyde (78-84-2) → (2R,3R)-3-Hydroxy-2,4-dimethyl-pentanoic acid benzyl ester

Conditions	Yield
Stage #1: benzyl proprionate With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane In hexane; dichloromethane at -95℃; for 1h; Stage #2: isobutyraldehyde In hexane; dichloromethane at -78 - 0℃; for 2h; Further stages.;	80%

benzyl proprionate (122-63-4) + 5-methyl-dihydro-furan-2-one (108-29-2) → benzyl (E)-2-[5-methyldihydrofuran-2(3H)-ylidene]propanoate

Conditions	Yield
Stage #1: benzyl proprionate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: 5-methyl-dihydro-furan-2-one In tetrahydrofuran; hexane Further stages.;	77%

Upstream product

• 137-40-6 sodium proprionate 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 75-03-6 ethyl iodide 
• 105-37-3 Ethyl propionate 
• 100-51-6 benzyl alcohol 
• 74-85-1 ethene 
• 123-62-6 propionic acid anhydride 
• 53772-44-4 benzyloxydiphenylphosphine 
• 802294-64-0 propionic acid 
• 55696-47-4 α,α-dipropionoxytoluene 
• 103-50-4 dibenzyl ether 
• 100-39-0 benzyl bromide 
• 123-38-6 propionaldehyde 

Downstream Products

• 848613-18-3 benzyl 2-methyl-3-phenylpropanoate 
• 108-88-3 toluene 
• 162662-03-5 benzyl 2-methyl-3-oxo-pentanoate 
• 173441-05-9 tert-butyl (3R,4S,5S)-4-(N-benzyloxycarbonylamino)-3-methoxy-5-methylheptanoate 
• 173653-47-9 benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate 
• 163768-51-2 benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate 
• 214333-77-4 benzyl 4-(benzyloxy)-2-methyl-3-oxobutanoate 
• 1199-77-5 α-methylcinnamic acid 
• 1352661-74-5 C₁₇H₂₂O₆ 
• 173653-48-0 benzyl (2S,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate 
• 149606-97-3 benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate 
• 60279-43-8 {Mo(CO)(dppe)2} 

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