2461-40-7

Basic information

• Product Name: Glycidyl butyrate
• Synonyms: glycidyl butyrate;(R)-2,3-epoxypropyl butyrate;2,3-EPOXYPROPYL ESTER BUTYRIC ACID;butyric acid glycidyl ester;oxiran-2-ylmethyl butanoate;Butyricacidoxiranylmethylester
• CAS NO: 2461-40-7
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• Product Categories: API intermediates
• Mol File: 2461-40-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 196.258 °C at 760 mmHg
• Flash Point: 85 °C
• Appearance: /
• Density: 1.069 g/cm³
• Vapor Pressure: 0.402mmHg at 25°C
• Refractive Index: 1.444
• CAS DataBase Reference: Glycidyl butyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Glycidyl butyrate(2461-40-7)
• EPA Substance Registry System: Glycidyl butyrate(2461-40-7)

Safety Data

• Hazardous Substances Data: 2461-40-7(Hazardous Substances Data)

Usage

General Description

Glycidyl butyrate is an organic compound with the chemical formula C7H12O3. It is an ester of butyric acid and glycidol and is commonly used as a flavor and fragrance ingredient. Glycidyl butyrate is a clear, colorless liquid that is slightly soluble in water but soluble in many organic solvents. It has a fruity and sweet odor, making it useful for providing a pleasant aroma in various products. In addition to its use in the food and fragrance industries, glycidyl butyrate is also utilized in the production of polymers and resins. Overall, glycidyl butyrate is a versatile chemical with a range of applications due to its unique properties.

InChI:InChI=1/C7H12O3/c1-2-3-7(8)10-5-6-4-9-6/h6H,2-5H2,1H3

Synthetic route

sodium butyrate (156-54-7) + epichlorohydrin (106-89-8) → (+/-)-glycidyl butyrate (2461-40-7)

Conditions	Yield
at 60℃; for 8h;	95%
With 15-crown-5 In acetonitrile for 14h; Ambient temperature;	92%
With tetrabutylammomium bromide In toluene for 5h; Solvent; Reflux;	90%
With 1,4-dioxane at 200℃;
With tetrabutylammomium bromide at 100℃; Kinetics; Temperature;

potassium n-butyrate (589-39-9) + epichlorohydrin (106-89-8) → (+/-)-glycidyl butyrate (2461-40-7)

Conditions	Yield
With tetrabutylammomium bromide In toluene for 5h; Solvent; Reflux;	70%

oxiranyl-methanol (556-52-5) + butyryl chloride (141-75-3) → (+/-)-glycidyl butyrate (2461-40-7)

Conditions	Yield
With triethylamine In toluene at 0℃; for 0.833333h;
Stage #1: oxiranyl-methanol With trimethylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: butyryl chloride In dichloromethane at 20℃; for 3h;

butanoic acid ethyl ester (105-54-4) + allyl alcohol (107-18-6) → (+/-)-glycidyl butyrate (2461-40-7) + allyl butyrate (2051-78-7) + oxiranyl-methanol (556-52-5)

Conditions	Yield
With Novozym 435; dihydrogen peroxide 1.) 15 min, 2.) 40 deg C, 16 h; Yield given. Multistep reaction. Yields of byproduct given;

allyl alcohol (107-18-6) → (+/-)-glycidyl butyrate (2461-40-7) + allyl butyrate (2051-78-7) + oxiranyl-methanol (556-52-5)

Conditions	Yield
With Novozym 435; C3H7COOC2H5; dihydrogen peroxide 1.) 15 min, 2.) 40 deg C, 16 h; Yield given. Multistep reaction. Yields of byproduct given;

(+/-)-glycidyl butyrate (2461-40-7) + 4-isopropylphenylisocyanate (31027-31-3) → <3-(4-isopropylphenyl)-2-oxo-5-oxazolidinyl>methyl butyrate (121373-21-5)

Conditions	Yield
With Tributylphosphine oxide; lithium bromide In xylene for 2h; Heating;	100%

(+/-)-glycidyl butyrate (2461-40-7) + ortho-methylphenyl iodide (615-37-2) + ethyl acrylate (140-88-5) → (E)-3-(2-(3-ethoxy-3-oxoprop-1-en-1-yl)-3-methylphenyl)-2-hydroxypropyl butyrate

Conditions	Yield
With potassium (1S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylate; palladium diacetate; XPhos In 1-methyl-pyrrolidin-2-one at 60℃; for 12h; Glovebox; Inert atmosphere; Sealed tube;	97%

(+/-)-glycidyl butyrate (2461-40-7) + ortho-methylphenyl iodide (615-37-2) + ethyl acrylate (140-88-5) → C19H26O5

Conditions	Yield
With palladium diacetate; potassium bicyclo[2.2.1]hept-2-ene-5-carboxylate; XPhos In 1-methyl-pyrrolidin-2-one at 60℃; for 12h;	97%

(+/-)-glycidyl butyrate (2461-40-7) + carbon dioxide (124-38-9) → (2-oxo-1,3-dioxolan-4-yl)methyl butyrate

Conditions	Yield
With 18-crown-6 ether at 120℃; under 39003.9 Torr; for 16h; Autoclave;	93%

(+/-)-glycidyl butyrate (2461-40-7) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → Butyric acid 3-cyano-2-hydroxy-propyl ester (142944-71-6)

Conditions	Yield
With triethylamine In tetrahydrofuran for 3.5h; Heating;	91%

(+/-)-glycidyl butyrate (2461-40-7) + methyl 4-iodo-3-methylbenzoate (5471-81-8) → methyl 7-methyl-2-(butyryloxymethyl)-2,3-dihydrobenzofuran-5-carboxylate

Conditions	Yield
With palladium diacetate; XPhos In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Inert atmosphere; Sealed tube;	91%
With palladium diacetate; potassium bicyclo[2.2.1]hept-2-ene-5-carboxylate; XPhos In 1-methyl-pyrrolidin-2-one at 80℃; for 24h;	91%

carbon disulfide (75-15-0) + (+/-)-glycidyl butyrate (2461-40-7) → C8H12O3S2

Conditions	Yield
Stage #1: (+/-)-glycidyl butyrate With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2 at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: carbon disulfide at 50℃; for 6h; Inert atmosphere;	91%

(+/-)-glycidyl butyrate (2461-40-7) + ortho-methylphenyl iodide (615-37-2) + tris-iso-propylsilyl acetylene (89343-06-6) → 2-hydroxy-3-(3-methyl-2-((triisopropylsilyl)ethynyl)phenyl)propyl butyrate

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; norborn-2-ene; potassium acetate; palladium diacetate; XPhos at 60℃; for 24h; Glovebox; Inert atmosphere; Sealed tube; regioselective reaction;	83%

(+/-)-glycidyl butyrate (2461-40-7) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → 4-butyryloxy-3-hydroxybutyric acid ethyl ester

Conditions	Yield
With 1,1-dimethyl-3,3-diethylguanidinecarbonylcobalt at 80℃; under 45004.5 Torr; for 24h; Autoclave;	79%
With 1,1-dimethyl-3,3-diethylguanidinecarbonylcobalt at 80℃; under 45004.5 Torr; for 24h; Autoclave; Schlenk technique;	79%

(+/-)-glycidyl butyrate (2461-40-7) + selenobutyric acid (787514-56-1) → C11H20O4Se (1040413-68-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; toluene at -30 - 20℃;	75%

(+/-)-glycidyl butyrate (2461-40-7) + (4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester (790703-40-1) → 3-(4-benzyloxy-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one

Conditions	Yield
Stage #1: (4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: (+/-)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;	65.5%

(+/-)-glycidyl butyrate (2461-40-7) → Butyric acid thiiranylmethyl ester (125188-61-6)

Conditions	Yield
With thiourea	60%

(+/-)-glycidyl butyrate (2461-40-7) → 1-sn-monobutyroylglycerol (5309-42-2) + (R)-glycidyl butyrate (60456-26-0) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3)

Conditions	Yield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;	A n/a B 46% C n/a

(+/-)-glycidyl butyrate (2461-40-7) → 1-sn-monobutyroylglycerol (5309-42-2) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3) + (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;	A n/a B n/a C 46%
With water; chiral ((substituted salen)Co)2-InCl3 at 20℃; for 3h;	A n/a B n/a C 45%
With water; (R,R)-[Co(salen)]2*GaCl3 at 20℃; for 4h;	A n/a B n/a C 43%
With water; chiral salen-based cobalt(II) complex at 20℃; for 4h;	A n/a B n/a C 40%

(+/-)-glycidyl butyrate (2461-40-7) → 1-sn-monobutyroylglycerol (5309-42-2) + (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃; for 16h;	A n/a B 46%
With 5CF3O3S(1-)*2Co(3+)*Y(3+)*2C36H52N2O2(2-); water In neat (no solvent) at 20℃; for 4h; Overall yield = 44 %; enantioselective reaction;	A n/a B n/a

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3)

Conditions	Yield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;	A 46% B n/a

(+/-)-glycidyl butyrate (2461-40-7) + (3-chlorophenyl) carbamic acid ethyl ester (2150-89-2) → 3-(3-chlorophenyl)-5-(hydroxymethyl)oxazolidin-2-one (42902-30-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - 20℃;	46%

(+/-)-glycidyl butyrate (2461-40-7) + ortho-methylphenyl iodide (615-37-2) → C14H18O3

Conditions	Yield
With [methanesulfonato(2-dicyclohexylphosphino-2',6'-di-isopropoxy-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II)]; C11H16O2; sodium acetate In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Glovebox;	46%

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (R)-oxiranemethanol (57044-25-4)

Conditions	Yield
With sodium phosphate buffer; 25 kDa lipase-like enzyme immobilized on DEAE-Sepharose In 1,4-dioxane; water at 25℃; for 10h; pH=7.00;	A n/a B 45%
With thermomyces lanuginosa In 1,4-dioxane; aq. phosphate buffer at 30℃; for 2h; pH=7; Temperature; Resolution of racemate; Enzymatic reaction;	A n/a B n/a

(+/-)-glycidyl butyrate (2461-40-7) → butyric acid-3-chloro-(S)-2-hydroxy-propyl ester (890051-54-4) + butyric acid-3-chloro-(R)-2-hydroxy-propyl ester (890051-57-7) + (R)-glycidyl butyrate (60456-26-0) + (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
With hydrogenchloride; (R,R)-[Co(salen)]2*GaCl3 In diethyl ether at 0 - 4℃; for 4h;	A 45% B n/a C n/a D 43%

(+/-)-glycidyl butyrate (2461-40-7) → (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
In tetrahydrofuran	44%

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3) + (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
With (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water In tetrahydrofuran at 0℃; for 12h; Jacobsen rearrangement; optical yield given as %ee;	A 40% B n/a C n/a

(+/-)-glycidyl butyrate (2461-40-7) + dibenzylamine (103-49-1) → 3-(N,N-dibenzylamino)-2-hydroxypropyl butyrate + 3-(N,N-dibenzylamino)-1-hydroxypropan-2-yl butyrate

Conditions	Yield
With ytterbium(III) triflate In tetrahydrofuran for 0.333333h; Heating; Yield given. Yields of byproduct given;

(+/-)-glycidyl butyrate (2461-40-7) → C7H9O3 (78906-37-3) + C7H11O3 (78906-48-6)

Conditions	Yield
With tert-butoxyl radical In various solvent(s)

(+/-)-glycidyl butyrate (2461-40-7) + 3-deazaadenine (6811-77-4) → Butyric acid (R)-3-(4-amino-imidazo[4,5-c]pyridin-1-yl)-2-hydroxy-propyl ester

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 5h;

(+/-)-glycidyl butyrate (2461-40-7) → Butyric acid 3-azido-2-hydroxy-propyl ester + Butyric acid 2-azido-3-hydroxy-propyl ester

Conditions	Yield
With hydrogenchloride; trimethylsilylazide; lithium isopropoxide; ytterbium(III) triflate 1) THF, r.t., 17 h, 2) THF; Yield given. Multistep reaction. Yields of byproduct given;

Upstream product

• 589-39-9 potassium n-butyrate 
• 106-89-8 epichlorohydrin 
• 105-54-4 butanoic acid ethyl ester 
• 107-18-6 allyl alcohol 
• 156-54-7 sodium butyrate 
• 556-52-5 oxiranyl-methanol 
• 141-75-3 butyryl chloride 

Downstream Products

• 5309-42-2 1-sn-monobutyroylglycerol 
• 60456-26-0 (R)-glycidyl butyrate 
• 126254-87-3 (S)-2,3-dihydroxypropyl butyrate 
• 2051-78-7 allyl butyrate 
• 29218-22-2 3-(3-fluoro-phenyl)-5-hydroxymethyl-oxazolidin-2-one 
• 42902-30-7 3-(3-chlorophenyl)-5-(hydroxymethyl)oxazolidin-2-one 
• 29218-26-6 5-hydroxymethyl-3-p-tolyl-oxazolidin-2-one 
• 65031-96-1 (S)-glycidyl butyrate 
• 556-52-5 oxiranyl-methanol 
• 890051-54-4 butyric acid-3-chloro-(S)-2-hydroxy-propyl ester 
• 890051-57-7 butyric acid-3-chloro-(R)-2-hydroxy-propyl ester 
• 57044-25-4 (R)-oxiranemethanol 
• 60456-23-7 (S)-oxiranemethanol 
• 121373-21-5 <3-(4-isopropylphenyl)-2-oxo-5-oxazolidinyl>methyl butyrate 

Relevant articles and documents

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