109-21-7

Basic information

• Product Name: Butyl butyrate
• Synonyms: 1-Butyl butyrate;1-butylbutyrate;Butanoic acid, butyl ester;Butanoicacid,butylester;Butanoicacidbutylester;Butyl butylate;Butyl ester of butanoic acid;Butyl n-butyrate
• CAS NO: 109-21-7
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21
• EINECS: 203-656-8
• Product Categories: A-BAlphabetic;Alpha Sort;B;BI - BZAnalytical Standards;Chemical Class;EstersAnalytical Standards;Solvents;Volatiles/ Semivolatiles;A-B;A-BFlavors and Fragrances;Alphabetical Listings;Certified Natural Products;Flavors and Fragrances;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 109-21-7.mol
• Article Data: 279

Chemical Properties

• Melting Point: -92 °C
• Boiling Point: 164-165 °C(lit.)
• Flash Point: 121 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.869 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.027mmHg at 25°C
• Refractive Index: n20/D 1.406(lit.)
• Storage Temp.: Flammables area
• Solubility: 0.50g/l
• Explosive Limit: 1%(V)
• Water Solubility: Soluble in water. (1 g/L).
• Merck: 14,1556
• BRN: 1747101
• CAS DataBase Reference: Butyl butyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Butyl butyrate(109-21-7)
• EPA Substance Registry System: Butyl butyrate(109-21-7)

Safety Data

• Statements: 10
• Safety Statements: 2-24/25
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• RTECS: ES8120000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 109-21-7(Hazardous Substances Data)

Usage

Description

Butyl butyrate is a kind of ester formed through the condensation of butyric acid and n-butanol. It has a pleasant flavor, and thus being used in the flavor industry to generate a sweet fruity flavor of pineapple-like. It occurs naturally in many kinds of fruits including apple, banana, berries, pear, plum, and strawberry. It is also found in alcoholic beverages. However, it should be noted that it is a marine pollutant, posing a threat to the marine environment. It may also penetrate into soil, contaminating groundwater and other nearby waterways.

References

https://pubchem.ncbi.nlm.nih.gov/compound/Butyl_butyrate#section=Top https://en.wikipedia.org/wiki/Butyl_butyrate

Chemical Properties

Different sources of media describe the Chemical Properties of 109-21-7 differently. You can refer to the following data:
1. CLEAR COLORLESS TO PALE YELLOWISH LIQUID
2. Butyl Butyrate is a liquid with a sweet, fruity odor. It is a volatile constituent of many fruits and honey and is used in fruit flavor compositions.
3. Butyl butyrate has a fruity (pear–pineapple-like) odor.

Occurrence

Reported found in fresh apple, apple juice, banana, orange juice, orange peel oil, melon, strawberry, Passiflora mollisima, soybean, honey and blue cheese.

Uses

Different sources of media describe the Uses of 109-21-7 differently. You can refer to the following data:
1. It is very important for the food and beverages industries and used as perfuming agents. It is a applied as a solvent for resins.
2. Butyl butyrate can be used as a reactant to synthesize: N-(Phenylmethyl)butanamide by reacting with benzylamine via ester-amide exchange reaction in the presence of supported graphene oxide catalyst.Cyclohexyl butyrate by acylation reaction with cyclohexanol using a ruthenium pincer PNN complex catalyst.Butyl ether by triiron dodecacarbonyl catalyzed hydrosilylation reaction.
3. Flavoring.

Definition

ChEBI: A butanoate ester of butan-1-ol.

Preparation

By passing vapors of n-butyl alcohol over MnO2 or ZnO at 400°C, also by passing vapors of n-butyl alcohol over CuO-VO at 180 to 200°C.

Aroma threshold values

Detection: 87 to 1000 ppb

Taste threshold values

Taste characteristics at 40 ppm: sweet, fresh, fruity, slightly fatty.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2605, 1947 DOI: 10.1021/ja01203a011Organic Syntheses, Coll. Vol. 1, p. 138, 1941Tetrahedron Letters, 22, p. 5327, 1981 DOI: 10.1016/S0040-4039(01)92493-1

General Description

A colorless liquid. Insoluble in water. A marine pollutant. Poses a threat to the aquatic environment. Immediate steps should be taken to prevent spread to the environment. May penetrate soils and contaminate groundwater and nearby waterways. Mildly irritates the eyes and skin.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Butyl butyrate reacts with acids to liberate heat along with butyl alcohol and butyric acid. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. May attack some forms of plastics [USCG, 1999].

Hazard

Irritant and narcotic. Moderate fire risk.

Health Hazard

Inhalation or ingestion causes headache, dizziness, nausea, vomiting, and narcosis. Contact with liquid irritates eyes.

Fire Hazard

Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot.

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic via intraperitoneal route. Mildly toxic by ingestion. Moderately irritating to eyes, sh, and mucous membranes by inhalation. Narcotic in hgh concentrations. Flammable liquid. To fight fire, use alcohol foam, foam, CO2, dry chemical. Incompatible with oxidizing materials. When heated to decomposition it emits acrid and irritating fumes.

InChI:InChI=1/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)/p-1

Synthetic route

butyric acid (107-92-6) + butan-1-ol (71-36-3) → butyl butyrate (109-21-7)

Conditions	Yield
With [Al(H2O)6][MS]3 In cyclohexane for 1h; Reagent/catalyst; Dean-Stark; Reflux;	100%
With Candida antarctica B lipase In 2,2,4-trimethylpentane at 40℃; for 3h; Enzymatic reaction;	98%
With DOOl-AlCl3 superacid resin for 1.5h; Heating;	97%

butan-1-ol (71-36-3) → butyl butyrate (109-21-7)

Conditions	Yield
With C29H44Cl2N2Ru; potassium tert-butylate In toluene for 15h; Reagent/catalyst; Time; Reflux;	100%
Ru complex at 118℃; for 12h; Inert atmosphere;	99%
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 2h;	99%

butyraldehyde (123-72-8) → butyl butyrate (109-21-7)

Conditions	Yield
With trimethylaluminum; benzene-1,2-diol; isopropyl alcohol In dichloromethane at 20℃; for 2h;	99%
With tris(bis(trimethylsilyl)amido)lanthanum(III) In hexane; pentane at -78 - 20℃;	45%
With aluminum ethoxide

butanoic acid anhydride (106-31-0) + butan-1-ol (71-36-3) → butyl butyrate (109-21-7)

Conditions	Yield
With ruthenium(III) 2,4-pentanedionate at 25℃; for 1h;	98%
CoCl2 In acetonitrile for 2h; Ambient temperature;	89%
With dmap; triethylamine In dichloromethane
In p-cymene at 50℃; Kinetics; Solvent;

1-Chloropropane (540-54-5) + propoxycarbonyl chloride (109-61-5) → butyl butyrate (109-21-7)

Conditions	Yield
Stage #1: 1-Chloropropane With magnesium; 1,2-dibromomethane In toluene at 60℃; for 3h; Inert atmosphere; Stage #2: propoxycarbonyl chloride With aluminum (III) chloride; manganese(ll) chloride In toluene at 0 - 20℃; for 2.25h; Inert atmosphere;	95%

triethylsilane (617-86-7) → triethylsilyl iodide (1112-49-8) + butyl butyrate (109-21-7)

Conditions	Yield
With butyryl iodide; bis(acetylacetonate)nickel(II) at 20℃; for 2h;	A 90% B 81%

butyryl iodide (78209-72-0) → triethylsilyl iodide (1112-49-8) + butyl butyrate (109-21-7)

Conditions	Yield
With triethylsilane; bis(acetylacetonate)nickel(II) at 20℃; for 2h;	A 90% B 81%

1-bromo-butane (109-65-9) + sodium butyrate (156-54-7) → butyl butyrate (109-21-7)

Conditions	Yield
With polyethylene glycol 400 at 65 - 70℃; for 3.5h;	90%

(PPh3)3CoH(N2) (21373-88-6, 16920-54-0) + phenyl butanoate (4346-18-3) → HCo(CO)(P(C6H5)3)3 (53729-69-4, 21329-67-9) + phenoxotris(triphenylphosphine)cobalt(I) (91583-66-3) + propane (74-98-6) + butyl butyrate (109-21-7) + nitrogen (7727-37-9)

Conditions	Yield
In toluene byproducts: H2; n-PrCO2Ph added to CoH(N2)(PPh3)3 in toluene in vac., reacted for 1 day at room temp.; liquid phase analysed by GLC; hexane added, ppt. filtered, washed with hexane, dried in vac., recrystd. from C6H6-hexane;	A n/a B 60% C 12% D 38% E 89%

butanoic acid ethyl ester (105-54-4) + butan-1-ol (71-36-3) → butyl butyrate (109-21-7)

Conditions	Yield
With rape seed lipase In hexane at 40℃; for 48h; Enzymatic reaction;	88%
With Candida antarctica lipase B (Novozym 435); 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; for 24h; Product distribution; Kinetics; Further Variations:; Reaction partners; Reagents;
With Candida antartica lipase B at 100℃; Enzyme kinetics; Further Variations:; Reagents; Temperatures;

butyraldehyde (123-72-8) → butyl butyrate (109-21-7) + butyric acid (107-92-6) + butan-1-ol (71-36-3)

Conditions	Yield
With dihydridotetrakis(triphenylphosphine)ruthenium; water; 1-Phenylbut-1-en-3-one In 1,2-dimethoxyethane at 180℃; for 24h; Product distribution; Mechanism; in the absence of hydrogen acceptor (benzalacetone); other aldehydes;	A n/a B 85% C n/a

triethylsilane (617-86-7) → triethylsilyl chloride (994-30-9) + butyl butyrate (109-21-7)

Conditions	Yield
With butyryl chloride; bis(acetylacetonate)nickel(II) at 90℃; for 2h;	A 83% B 68%

n-pentyldimethylsilane (29681-51-4) → butyl butyrate (109-21-7) + dimethylpentylsilylchloride (25938-34-5)

Conditions	Yield
With butyryl chloride; bis(acetylacetonate)nickel(II) at 90℃; for 2h;	A 69% B 81%

dimethylhexylsilane (63246-85-5) → butyl butyrate (109-21-7) + dimethylhexylsilyl chloride (3634-59-1)

Conditions	Yield
With butyryl chloride; bis(acetylacetonate)nickel(II) at 90℃; for 2h;	A 64% B 81%

butanoic acid anhydride (106-31-0) + (PPh3)3CoH(N2) (21373-88-6, 16920-54-0) → Co(OCO-n-C3H7) (99668-71-0) + propane (74-98-6) + butyl butyrate (109-21-7) + nitrogen (7727-37-9) + hydrogen (1333-74-0)

Conditions	Yield
In toluene in toluene at room temp. for 1 day;	A n/a B 16% C 30% D 81% E 13%

butyryl chloride (141-75-3) → butyl butyrate (109-21-7)

Conditions	Yield
With triethylsilane; iron(III)-acetylacetonate at 20℃;	80%

dihydridotetrakis(triphenylphosphine)ruthenium (27599-25-3, 54083-06-6, 19529-00-1) + butyraldehyde (123-72-8) → RuH(OCOC3H7)(P(C6H5)3)3 (25087-79-0) + butyl butyrate (109-21-7) + butan-1-ol (71-36-3)

Conditions	Yield
In neat (no solvent) educts mixed at in vac., stirred at -30°C for 2 h; evapd. in vac., solid washed with Et2O and hexane, dissolved in toluene, filtered, concd. in vac., ppt. filtered, washed with hexane, dried in vac.;	A 80% B n/a C <1
In neat (no solvent) educts mixed at in vac., stirred at 0°C for 2 h; evapd. in vac., solid washed with Et2O and hexane, dissolved in toluene, filtered, concd. in vac., ppt. filtered, washed with hexane, dried in vac.;	A n/a B 0% C <1

propyl cyanide (109-74-0) + butan-1-ol (71-36-3) → butyl butyrate (109-21-7)

Conditions	Yield
With Bromotrichloromethane; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate at 20℃; for 12h; Irradiation; Inert atmosphere;	80%

butan-1-ol (71-36-3) → butyl butyrate (109-21-7) + butyraldehyde (123-72-8)

Conditions	Yield
With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate In dichloromethane; water at 20 - 25℃; for 3h;	A 79.7% B 20.3%
With sodium chlorate; sulfuric acid; vanadia
With chromium(III) oxide; sulfuric acid

normal butyl hypochlorite (5923-22-8) → butyl butyrate (109-21-7)

Conditions	Yield
In tetrachloromethane for 4h; Irradiation;	78%
In benzene Ambient temperature; Irradiation;	78%

butan-1-ol (71-36-3) → butyl butyrate (109-21-7) + butyric acid (107-92-6)

Conditions	Yield
With sodium bromate; sodium hydrogensulfite for 2h; Ambient temperature;	A 76% B 5%
With sodium bromate; sodium hydrogensulfite for 2h; Product distribution; Mechanism; Ambient temperature; other primary alcohols and α,ω-diols, var. solvents, temp. and time;	A 76% B 5%
With [pentamethylcyclopentadienyl*Ir(2,2′-bpyO)(OH)][Na]; sodium hydroxide In water for 40h; Time; Reflux; Inert atmosphere;	A 22% B 70%

butyryl chloride (141-75-3) → methyldiethylchlorosilane (17680-28-3) + butyl butyrate (109-21-7)

Conditions	Yield
With diethylmethylsilane; bis(acetylacetonate)nickel(II) at 90℃; for 2h;	A 76% B 68%

1-butoxy-1-isobutoxy butane (20266-12-0) → 2-methyl-propan-1-ol (78-83-1) + butyl butyrate (109-21-7) + isobutyl n-butyrate (539-90-2) + isobutyric Acid (79-31-2) + butyric acid (107-92-6) + butan-1-ol (71-36-3)

Conditions	Yield
With oxygen; cobalt(II) acetate at 90℃; under 750.06 Torr; Mechanism; Rate constant; other oxygen pressure;	A 5.5% B 3% C 3.5% D 5% E 73.5% F 7%

dibutyl ether (142-96-1) → butyl butyrate (109-21-7)

Conditions	Yield
With manganese (VII)-oxide In tetrachloromethane; acetone at -45℃;	73%
With zinc dichromate(VI) In dichloromethane for 3h; Ambient temperature;	60%
With sodium bromate; hydrogen bromide In dichloromethane at 35 - 40℃; for 20h;	54%

Octanal (124-13-0) + butan-1-ol (71-36-3) → butyl butyrate (109-21-7) + Octanoic acid (124-07-2) + butyl octanoate (589-75-3)

Conditions	Yield
With sodium bromate; sodium hydrogensulfite for 2h; Ambient temperature;	A 17% B 13% C 70%

dibutyl ether (142-96-1) + butyryl chloride (141-75-3) → octane-4,5-dione (5455-24-3) + butyl butyrate (109-21-7)

Conditions	Yield
CoCl2 In acetonitrile Ambient temperature;	A 10% B 68%

dibutyl ether (142-96-1) → butyl butyrate (109-21-7) + butyric acid (107-92-6) + butan-1-ol (71-36-3)

Conditions	Yield
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 4h;	A 65% B 8% C 10%

ethanol (64-17-5) + crotonaldehyde (123-73-9) → ethyl crotonate (10544-63-5) + butyl butyrate (109-21-7) + butan-1-ol (71-36-3)

Conditions	Yield
With sodium carbonate; rhodium(III) chloride; triphenylphosphine for 5h; Heating;	A 8 % Chromat. B 61% C 31%

crotonaldehyde (123-73-9) → ethyl crotonate (10544-63-5) + butyl butyrate (109-21-7) + butan-1-ol (71-36-3)

Conditions	Yield
With ethanol; sodium carbonate; rhodium(III) chloride; triphenylphosphine for 5h; Heating;	A 8% B 61% C 31%

butyl butyrate (109-21-7) → butan-1-ol (71-36-3)

Conditions	Yield
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;	98%
With hydrogen at 223.84℃; under 5625.56 Torr; Kinetics; Thermodynamic data; Concentration; Pressure; Temperature; neat (no solvent, gas phase);
With [RuH(η2-BH4)(2-di-tert-butylphosphinomethyl-6-diethylaminomethylpyridine)]; hydrogen In tetrahydrofuran at 110℃; under 7600.51 Torr; for 12h; Autoclave;	97 %Chromat.

hexan-1-amine (111-26-2) + butyl butyrate (109-21-7) → N-hexylbutanamide (10264-17-2)

Conditions	Yield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 24h; Inert atmosphere;	97%

morpholine (110-91-8) + butyl butyrate (109-21-7) → (N-morpholin-4-yl)butan-1-one (5327-51-5)

Conditions	Yield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 21h; Inert atmosphere;	95%
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium tert-butylate In toluene at 120℃; for 48h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;	55%

piperidine (110-89-4) + butyl butyrate (109-21-7) → 1-(piperidin-1-yl)butan-1-one (4637-70-1)

Conditions	Yield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 19h; Inert atmosphere;	94%

1-methyl-piperazine (109-01-3) + butyl butyrate (109-21-7) → 1-(4-methylpiperazin-1-yl)butan-1-one (10001-51-1)

Conditions	Yield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene; benzene at 135℃; for 24h; Inert atmosphere;	94%

butyl butyrate (109-21-7) + cyclohexanol (108-93-0) → cyclohexyl butyrate (1551-44-6)

Conditions	Yield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In toluene for 34h; Inert atmosphere; Reflux;	92%

butyl butyrate (109-21-7) + para-fluorobenzylamine (140-75-0) → N-(4-fluorobenzyl)butyramide

Conditions	Yield
With C31H40MnN2O3P*C6H14O; potassium tert-butylate In toluene; 1,3,5-trimethyl-benzene at 110℃; for 48h; Schlenk technique;	88%

bromobenzene (108-86-1) + butyl butyrate (109-21-7) → 1,1-diphenylbutan-1-ol (5331-17-9)

Conditions	Yield
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; Barbier Coupling Reaction; chemoselective reaction;	87%
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; chemoselective reaction;	87%

butyl butyrate (109-21-7) + phenethylamine (64-04-0) → N-(2-phenylethyl)butanamide (6283-13-2)

Conditions	Yield
With C31H40MnN2O3P*C6H14O; potassium tert-butylate In toluene; 1,3,5-trimethyl-benzene at 110℃; for 48h; Schlenk technique;	85%

butyl butyrate (109-21-7) + para-bromotoluene (106-38-7) → 1,1-di(p-tolyl)butan-1-ol (31067-10-4)

Conditions	Yield
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; Barbier Coupling Reaction; chemoselective reaction;	83%
With magnesium; copper(II) oxide In tetrahydrofuran at 65℃; for 4h; chemoselective reaction;	83%

butyl butyrate (109-21-7) + benzylamine (100-46-9) → N-benzylbutyramide (10264-14-9)

Conditions	Yield
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium tert-butylate In toluene at 120℃; for 48h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;	82%

butyl butyrate (109-21-7) + aniline (62-53-3) → N-phenylbutyramide (1129-50-6)

Conditions	Yield
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium tert-butylate In toluene at 120℃; for 48h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;	80%

Upstream product

• 1313-13-9 Manganese dioxide 
• 1314-13-2 Zinc oxide 

Downstream Products

• 1759-53-1 Cyclopropanecarboxylic acid 

Recommend Products

• 67-64-1  acetone 
• 71-36-3  butan-1-ol 
• 1112-49-8  triethylsilyl iodide 
• 617-86-7  triethylsilane 
• 106-98-9  1-butylene 
• 107-01-7  butene-2 
• 123-38-6  propionaldehyde 
• 123-72-8  butyraldehyde 
• 107-02-8  acrolein 
• 3634-59-1  dimethylhexylsilyl chloride 
• 63246-85-5  hexyldimethylsilane 
• 136-60-7  benzoic acid, butyl ester 
• 100-51-6  benzyl alcohol 
• 100-52-7  benzaldehyde