103-38-8

Basic information

• Product Name: BENZYL ISOVALERATE
• Synonyms: 3-methylbutanoicacidphenylmethylester;3-methyl-butanoicaciphenylethylester;3-methyl-butanoicaciphenylmethylester;Benzyl isopentanoate;Butanoic acid, 3-methyl-, phenylethyl ester;Butanoic acid, 3-methyl-, phenylmethyl ester;Butanoicacid,3-methyl-,phenylmethylester;Isopentanoic acid, phenylmethyl ester
• CAS NO: 103-38-8
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• EINECS: 203-106-7
• Mol File: 103-38-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 116 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.988 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0294mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Water Solubility: 238.219mg/L at 30℃
• CAS DataBase Reference: BENZYL ISOVALERATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL ISOVALERATE(103-38-8)
• EPA Substance Registry System: BENZYL ISOVALERATE(103-38-8)

Safety Data

• Statements: 36/38
• Safety Statements: 24/25-37-26
• WGK Germany: 2
• RTECS: NY1415000
• TSCA: Yes
• Hazardous Substances Data: 103-38-8(Hazardous Substances Data)

Usage

Description

BENZYL ISOVALERATE is a liquid with a heavy, floral odor and a powerful, fruity apple scent. It is found in cherimoya, sapodilla fruit, and lambs' lettuce, and is used in perfumery for oriental and heavy blossom odors.

Uses

Used in Flavor Industry:
BENZYL ISOVALERATE is used as a flavoring agent for its sweet, fruity, and balsamic taste with tropical and dried fruit nuances.
Used in Perfumery Industry:
BENZYL ISOVALERATE is used as a fragrance ingredient for its heavy, floral, and oriental scent.

Preparation

May be prepared by esterification of isovaleric acid with benzyl alcohol.

InChI:InChI=1/C12H16O2/c1-10(2)8-12(13)14-9-11-6-4-3-5-7-11/h3-7,10H,8-9H2,1-2H3

Synthetic route

Ethyl isovalerate (108-64-5) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
titanium tetrachloride In toluene for 4h; Heating;	98%
titanium tetrachloride In toluene for 4h; Heating / reflux;	98%

C12H16N2O2 (1160845-88-4) → benzyl isovalerate (103-38-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform for 24h; Reflux;	80%

benzyl crotonate (71338-71-1, 92758-75-3, 65416-24-2) + methylcopper (1184-53-8) → benzyl isovalerate (103-38-8)

Conditions	Yield
With chloromethylsilane In dichloromethane for 4h; Ambient temperature;	76%

3-methyl-1-oxobutan-2-yl 4-nitrobenzoate (1262801-37-5) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; triethylamine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	74%

3,3-dimethyl acrylaldehyde (107-86-8) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With 1,4-bis[2,6-di(2-propyl)phenyl]-3-phenyl-1H-1,2,4-triazol-4-ium chloride; N-ethyl-N,N-diisopropylamine at 100℃; for 10h;	72%

aluminum ethoxide (555-75-9) + benzaldehyde (100-52-7) + isovaleraldehyde (590-86-3) → isoamyl benzoate (94-46-2) + benzyl isovalerate (103-38-8)

benzaldehyde (100-52-7) + isovaleraldehyde (590-86-3) → isoamyl benzoate (94-46-2) + benzyl isovalerate (103-38-8)

benzaldehyde (100-52-7) + isovaleraldehyde (590-86-3) → benzyl isovalerate (103-38-8)

Conditions	Yield
With aluminum ethoxide

sodium isovalerate (539-66-2) + benzyl chloride (100-44-7) → benzyl isovalerate (103-38-8)

sodium isovalerate (539-66-2) + benzyl chloroformate (501-53-1) → benzyl isovalerate (103-38-8)

isopentanoyl chloride (108-12-3) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With pyridine

3-methylbutyric acid (503-74-2) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With sulfuric acid
at 280 - 300℃; beim Leiten ueber TiO2;
unter Entfernung des gebildeten Wassers;

Isovaleric anhydride (1468-39-9) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

benzaldehyde di(neopentyl) acetal (94231-95-5) → isoamyl benzoate (94-46-2) + ((isopentyloxy)methyl)benzene (122-73-6) + benzyl isovalerate (103-38-8) + α-isopropyl cinnamaldehyde (75101-96-1) + benzaldehyde (100-52-7) + benzyl alcohol (100-51-6)

Conditions	Yield
With antimonypentachloride In 1,2-dichloro-ethane at 30℃; for 0.5h; Product distribution; Mechanism; action of Lewis acids, ferric chloride also used;

dimethylketene (598-26-5) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
boron trifluoride diethyl etherate In diethyl ether at 25℃; Rate constant; Mechanism; var. conc. of cat.;

isopentanoyl chloride (108-12-3) + sodium benzylate → benzyl isovalerate (103-38-8)

3-methyl-1-oxobutan-2-yl benzoate + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1H-imidazole; caesium carbonate In toluene at 20℃; Inert atmosphere;

3-methyl-1-oxobutan-2-yl o-nitrobenzoate (1262801-35-3) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; triethylamine In toluene at 20℃; Inert atmosphere;

3-methyl-1-oxobutan-2-yl m-nitrobenzoate (1262801-36-4) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; triethylamine In toluene at 20℃; Inert atmosphere;

3-methylbutyroyl fluoride (352-66-9) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;

isovaleraldehyde (590-86-3) → benzyl isovalerate (103-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: difluoro[4-(trifluoromethyl)phenyl]-λ3-bromane / dichloromethane / 3 h / 0 °C / Inert atmosphere 2: triethylamine / dichloromethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: dibromoisocyanuric acid / dichloromethane / 2 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.33 h / 20 °C View Scheme

isovaleryl bromide (35447-68-8) + benzyl alcohol (100-51-6) → benzyl isovalerate (103-38-8)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.333333h;	348 mg

carbon dioxide (124-38-9) + benzyl isovalerate (103-38-8) → 2-((benzyloxy)carbonyl)-3-methylbutanoic acid (1430413-87-8)

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -70℃; for 0.333333h;	88%

1-nitroethylene (3638-64-0) + benzyl isovalerate (103-38-8) → 3-methyl-2-(2-nitro-ethyl)-butyric acid benzyl ester

Conditions	Yield
With diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane -78 deg C, 1 h; -78 deg C to room temp., 35 min;	77%

benzyl isovalerate (103-38-8) + N-butoxycarbonyl-L-phenylalanine anhydride (142955-51-9) → (S)-4-tert-Butoxycarbonylamino-2-isopropyl-3-oxo-5-phenyl-pentanoic acid benzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	63%

benzyl isovalerate (103-38-8) + BOC-L-alanine-NCA (125814-30-4) → (S)-4-tert-Butoxycarbonylamino-2-isopropyl-3-oxo-pentanoic acid benzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	59%

benzyl isovalerate (103-38-8) + Nα-carbobenzyloxy-L-phenylalanine N-carboxanhydride (25613-60-9) → (S)-4-Benzyloxycarbonylamino-2-isopropyl-3-oxo-5-phenyl-pentanoic acid benzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	52%

benzyl isovalerate (103-38-8) + (S)-4-Benzyloxymethyl-2,5-dioxo-oxazolidine-3-carboxylic acid tert-butyl ester (125814-31-5) → (S)-5-Benzyloxy-4-tert-butoxycarbonylamino-2-isopropyl-3-oxo-pentanoic acid benzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	50%

benzyl isovalerate (103-38-8) + N-(tert-butoxycarbonyl)-L-leucine N-carboxyanhydride → (S)-4-tert-Butoxycarbonylamino-2-isopropyl-6-methyl-3-oxo-heptanoic acid benzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	50%

bromoacetic acid tert-butyl ester (5292-43-3) + benzyl isovalerate (103-38-8) → C18H26O4 (894147-72-9)

Conditions	Yield
Stage #1: benzyl isovalerate With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran at 0 - 20℃; Further stages.;	48%

benzyl isovalerate (103-38-8) + (S)-4-(2-Benzyloxycarbonyl-ethyl)-2,5-dioxo-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-4-tert-Butoxycarbonylamino-2-isopropyl-3-oxo-heptanedioic acid dibenzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	46%

benzyl isovalerate (103-38-8) + Z-L-Ala-NCA → (S)-4-Benzyloxycarbonylamino-2-isopropyl-3-oxo-pentanoic acid benzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	43%

benzyl isovalerate (103-38-8) + (S)-4-Benzyloxycarbonylmethyl-2,5-dioxo-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-4-tert-Butoxycarbonylamino-2-isopropyl-3-oxo-hexanedioic acid dibenzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	42%

benzyl isovalerate (103-38-8) + (S)-3-benzyloxycarbonyl-4-isopropyl-2,5-oxazolidinedione → (S)-4-Benzyloxycarbonylamino-2-isopropyl-5-methyl-3-oxo-hexanoic acid benzyl ester

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h;	40%

Upstream product

• 555-75-9 aluminum ethoxide 
• 100-52-7 benzaldehyde 
• 590-86-3 isovaleraldehyde 
• 539-66-2 sodium isovalerate 
• 501-53-1 benzyl chloroformate 
• 108-12-3 isopentanoyl chloride 
• 100-51-6 benzyl alcohol 
• 503-74-2 3-methylbutyric acid 
• 1468-39-9 Isovaleric anhydride 
• 71338-71-1 benzyl crotonate 
• 1184-53-8 methylcopper 
• 108-64-5 Ethyl isovalerate 
• 1160845-88-4 C₁₂H₁₆N₂O₂ 
• 352-66-9 3-methylbutyroyl fluoride 

Downstream Products

• 894147-72-9 C₁₈H₂₆O₄ 
• 503-74-2 3-methylbutyric acid 
• 1430413-87-8 2-((benzyloxy)carbonyl)-3-methylbutanoic acid 

Relevant articles and documents

A highly selective, high-speed, and hydrolysis-free O-acylation in subcritical water in the absence of a catalyst

(Chemical Equation Presented) Fast and furious: A wide range of alcohols are acylated by acetic anhydride, in the absence of catalyst, in subcritical water in a flow-type microreaction system. The esters are selectively produced in high yields at temperatures of 200 to 250°C. Varying the amount of acetic anhydride added with respect to the alcohols allows the regioselective acylation of one or both hydroxy groups of various dihydroxy compounds (see picture).

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required

A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.

Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ3-bromane

Oxidation of primary aliphatic aldehydes with p- trifluoromethylphenyl(difluoro)-λ3-bromane in dichloromethane at 0 °C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.