4-Hexanolide supplier | CasNO.695-06-7

Name
4-Hexanolide
EINECS 211-778-8
CAS No. 695-06-7
Article Data70
CAS DataBase
Density 1.003 g/cm³
Solubility 77g/L at 20℃
Melting Point -18 °C
Formula C₆H₁₀O₂
Boiling Point 214.904 °C at 760 mmHg
Molecular Weight 114.144
Flash Point 79.338 °C
Transport Information
Appearance colourless to pale yellow liquid with a herbaceous, sweet odour
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Caproicacid, g-hydroxy-, lactone (4CI);Hexanoic acid, 4-hydroxy-, g-lactone (7CI);4-Ethyl-4-butanolide;4-Hydroxyhexanoic acid lactone;5-Ethyldihydro-2(3H)-furanone;5-Ethyltetrahydro-2-furanone;g-Ethyl-g-butyrolactone;
PSA 26.30000
LogP 1.10200

Synthetic route

: 2407-43-4
5-ethyl-5H-furan-2-one

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With dodecacarbonyltetrarhodium(0); triphenylphosphine; isopropyl alcohol at 220℃; for 1h;	91%

: (4R,5S)-5-Ethyl-4-iodo-dihydro-furan-2-one

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With nickel; isopropyl alcohol for 0.25h; Heating;	90%

: 4219-24-3
hex-3-enoic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V) at 80℃; for 2h; Sealed tube;	88%
With chloro-trimethyl-silane; water; sodium iodide In hexane for 44h; Ambient temperature;	66%

: 823-22-3, 26991-67-3
5-hexanolide

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With W(OTf)6 at 180℃; for 10h; Schlenk technique; Ionic liquid; Inert atmosphere; Green chemistry;	86%
With hydrogen iodide at 125℃; for 4h;

: 128756-18-3
4-Methoxymethoxy-hexanoic acid trimethylhydrazide

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With perchloric acid In dichloromethane for 8h; Ambient temperature;	85%

: 502-44-3
hexahydro-2H-oxepin-2-one

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With W(OTf)6 at 180℃; for 10h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Schlenk technique; Ionic liquid; Inert atmosphere; Green chemistry;	85%
With silica-alumina In water at 374.84℃; under 750.075 Torr; Kinetics; Flow conditions;
With W(OTf)6 at 150℃; for 10h; Reagent/catalyst; Temperature; Green chemistry;	99 %Chromat.

: 51827-43-1
γ-Hydroxycapronitril

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With Rhodococcus rhodochrous IFO 15564 at 30℃; phosphate buffer, pH 6;	79%

: 1577-18-0
(E)-3-hexenoic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In nitromethane for 3h; Heating;	77%
With sulfuric acid

: 106-88-7
ethyloxirane

: C20H15NP(1-)*Na(1+)

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
In benzene alkalical hydrolysis;	71%

: 19781-77-2
hept-6-en-3-ol

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With cethyltrimethylammonium permanganate In chloroform at 25℃; for 4h;	69%
With (bipyH2)-CrOCl5 In dichloromethane Heating;	40%

: 29474-78-0
D-allono-1,4-lactone

A: 695-06-7
hexan-4-olide

B: 62885-37-4
4-Iodohexanoic acid

C: 5-Iodohexanoic acid

Conditions

Conditions	Yield
With hydrogen iodide at 125℃; for 4h;	A 67% B 7% C 14%

...Expand

: 90-80-2
D-Glucono-1,5-lactone

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With hydrogen iodide at 125℃; for 4h;	67%

: 89701-67-7
5-Acetyloxyhexanenitrile

A: 695-06-7
hexan-4-olide

B: 823-22-3, 26991-67-3
5-hexanolide

Conditions

Conditions	Yield
With sulfuric acid at 130℃; Yields of byproduct given;	A 62% B n/a

: 142-62-1
hexanoic acid

A: 695-06-7
hexan-4-olide

B: 823-22-3, 26991-67-3
5-hexanolide

Conditions

Conditions	Yield
With sodium persulfate In water at 85 - 90℃; for 5h;	A 60% B 22%

: 1191-25-9
6-Hydroxyhexanoic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With W(OTf)6 at 180℃; for 10h; Schlenk technique; Ionic liquid; Inert atmosphere; Green chemistry;	57%
With aluminium(III) triflate at 200℃; for 10h; Reagent/catalyst; Temperature; Green chemistry;	96 %Chromat.

: 110-44-1
hexa-2,4-dienoic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With chloro-trimethyl-silane; water; sodium iodide In hexane for 18h; Heating;	54%

: 19781-77-2
hept-6-en-3-ol

A: 695-06-7
hexan-4-olide

B: 2565-39-1
hept-6-en-3-one

Conditions

Conditions	Yield
With chromium(V)	A 40% B 50%
With potassium permanganate; water; copper(II) sulfate In dichloromethane 1.) reflux, 5 min, 2.) RT, 4 h; Yield given. Yields of byproduct given;

: 628-62-6
heptanamide

A: 695-06-7
hexan-4-olide

B: 142-62-1
hexanoic acid

C: 823-22-3, 26991-67-3
5-hexanolide

Conditions

Conditions	Yield
With sodium persulfate; copper dichloride at 85 - 90℃; for 5h;	A 38% B 42% C 18%

...Expand

: 76543-09-4
methyl 3-(oxiran-2-yl)propanoate

: 75-16-1
methylmagnesium bromide

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
Stage #1: methylmagnesium bromide With copper(l) iodide In tetrahydrofuran; diethyl ether at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl 3-(oxiran-2-yl)propanoate In tetrahydrofuran; diethyl ether at -30℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; diethyl ether; water	42%

: 628-02-4
Caproamide

A: 695-06-7
hexan-4-olide

B: 142-62-1
hexanoic acid

C: 823-22-3, 26991-67-3
5-hexanolide

Conditions

Conditions	Yield
With sodium persulfate; sodium chloride In water at 85 - 90℃; for 10h;	A 40% B 41% C 19%
With sodium persulfate; sodium chloride In water at 85 - 90℃; for 10h;	A 40 % Chromat. B 41 % Chromat. C 19%
With sodium persulfate; sodium chloride In water at 85 - 90℃; for 10h;	A 40 % Chromat. B 41 % Chromat. C 19 % Chromat.

...Expand

: 76543-09-4
methyl 3-(oxiran-2-yl)propanoate

: 917-54-4
methyllithium

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
Stage #1: methyllithium With copper(I) cyanide In tetrahydrofuran; diethyl ether at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl 3-(oxiran-2-yl)propanoate In tetrahydrofuran; diethyl ether at -30℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; diethyl ether; water	40%

: 1577-20-4
(E)-hex-4-enoic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With 1-Cyanonaphthalene; biphenyl In water; acetonitrile for 13.3333h;	36%

: 32730-32-8
5-bromomethyl-γ-butyrolactone

: 917-54-4
methyllithium

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
Stage #1: methyllithium With copper(l) iodide In diethyl ether at 0℃; for 0.25h; Inert atmosphere; Stage #2: 5-bromomethyl-γ-butyrolactone In diethyl ether at -70 - 0℃; for 5.5h; Inert atmosphere; Stage #3: With ammonium chloride In diethyl ether; water	34%

: 110-44-1
sorbic Acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid; zinc at 85℃;
With hydrogenchloride; tin(ll) chloride at 85℃; Reagens 4: Eisessig;
With hydrogenchloride; tin at 85℃; Reagens 4: Eisessig;

: 28274-28-4
2-ethyl-5-oxo-tetrahydro-furan-3-carboxylic acid

A: 695-06-7
hexan-4-olide

B: 4219-24-3
hex-3-enoic acid

Conditions

Conditions	Yield
bei der Destillation;

: 127727-92-8
trans-3-hexenenitrile

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With sulfuric acid

: 13419-69-7
(E)-2-Hexenoic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With sulfuric acid

: 1577-22-6
5-hexenoic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With PPA at 70℃;

: 688-99-3
5-hexen-3-ol

A: 695-06-7
hexan-4-olide

B: 1117-74-4
4-oxohexanoic acid

Conditions

Conditions	Yield
With sodium dichromate; dimethylsulfide borane complex; sulfuric acid 1.) Et2O, a) -78 to 25 deg C, b) 25 deg C, 12 h, 2.) reflux, 1 h; Yield given. Multistep reaction;

: 13532-38-2, 87241-93-8, 97189-67-8
γ-Hydroxycaproic acid

: 695-06-7
hexan-4-olide

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 0℃; for 1h; Yield given;

: 695-06-7
hexan-4-olide

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 4,4,5,5-tetramethyl-2-((4-((3,3,4,4-tetramethylborolan-1-yl)oxy)hexyl)oxy)-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With C12H36MgN2Si4 In neat (no solvent) at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	99%

: 695-06-7
hexan-4-olide

: 142-62-1
hexanoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; W(OTf)6; hydrogen at 135℃; under 760.051 Torr; for 12h;	97%
With palladium on activated carbon; W(OTf)6; hydrogen In neat (no solvent) at 135℃; under 760.051 Torr; for 12h;	94%

: 695-06-7
hexan-4-olide

: 201230-82-2
carbon monoxide

: 626-70-0
2-methylhexane-1,6-dioic acid

Conditions

Conditions	Yield
With hexafluoroantimonic acid at 0℃; for 1h;	96%

: 695-06-7
hexan-4-olide

: 111-26-2
hexan-1-amine

: 1378491-89-4
N-hexyl-4-hydroxyhexanamide

Conditions

Conditions	Yield
With sodium methylate In toluene at 50℃; for 70h; Inert atmosphere;	94%

: 695-06-7
hexan-4-olide

: 16432-53-4
hexane-1,4-diol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 16h; Inert atmosphere;	92%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;	77%
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Ambient temperature; Yield given;

: 695-06-7
hexan-4-olide

: 5-ethyl-dihydro-furan-2-thione

Conditions

Conditions	Yield
With Lawessons reagent; Hexamethyldisiloxane at 120℃; for 0.025h; microwave irradiation;	92%

: 695-06-7
hexan-4-olide

: 4039-82-1
Benzyl propargyl ether

: 1-benzyloxy-7-hydroxynon-2-yn-4-one

Conditions

Conditions	Yield
Stage #1: Benzyl propargyl ether With n-butyllithium In tetrahydrofuran at -78 - -30℃; Stage #2: hexan-4-olide With boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 20℃; for 1h;	92%

: 695-06-7
hexan-4-olide

: 30414-44-9
5-ethyltetrahydrofuran-2-ol

Conditions

Conditions	Yield
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 1h;	91%
With diisobutylaluminium hydride In tetrahydrofuran at -78℃;	85%
Stage #1: hexan-4-olide With diisobutylaluminium hydride In toluene at -63 - -61℃; for 1.5h; Inert atmosphere; Stage #2: With methanol In diethyl ether; toluene at 20℃;	52%
Stage #1: hexan-4-olide With diisobutylaluminium hydride In toluene at -63 - -61℃; for 1.5h; Inert atmosphere; Stage #2: With methanol In diethyl ether; toluene at 20℃;
Stage #1: hexan-4-olide With diisobutylaluminium hydride In hexane; dichloromethane at -75 - -70℃; for 4.5h; Stage #2: With water; ammonium chloride In hexane; dichloromethane Cooling with ice;

: 695-06-7
hexan-4-olide

: 75-77-4
chloro-trimethyl-silane

: 34939-91-8, 58648-56-9
dimethyl lithiomethylphosphonate

: (2-oxo-5-trimethylsilanyloxy-heptyl)-phosphonic acid dimethyl ester

Conditions

Conditions	Yield
Stage #1: hexan-4-olide; dimethyl lithiomethylphosphonate Stage #2: With lithium diisopropyl amide Stage #3: chloro-trimethyl-silane	90%

...Expand

: 695-06-7
hexan-4-olide

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

: C15H29N2O3

Conditions

Conditions	Yield
at 130℃; for 2h;	89%

: 695-06-7
hexan-4-olide

: 40726-47-4
4-hydroxyhexanamide

Conditions

Conditions	Yield
With ammonia at 20℃; for 240h;	87%
With ethanol; ammonia at 100℃;
With ammonia; water durch Schuetteln;

: 695-06-7
hexan-4-olide

: 1666-13-3
diphenyl diselenide

: 5-ethyl-3-(phenylselanyl)dihydrofuran-2(3H)-one

Conditions

Conditions	Yield
Stage #1: hexan-4-olide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.25h; Stage #2: diphenyl diselenide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78 - -40℃;	87%

: 695-06-7
hexan-4-olide

: 20487-40-5
tert-butyl propionate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 3,6-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oct-2-enoic acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: tert-butyl propionate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Stage #2: hexan-4-olide In tetrahydrofuran; hexane at -78℃; for 2h; Stage #3: tert-butyldimethylsilyl chloride With tert-butoxide In tetrahydrofuran at 20℃;	86%

...Expand

: 695-06-7
hexan-4-olide

: 540-88-5
acetic acid tert-butyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 3,6-bis-(tert-butyl-dimethyl-silanyloxy)-oct-2-enoic acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: acetic acid tert-butyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Stage #2: hexan-4-olide In tetrahydrofuran; hexane at -78℃; Stage #3: tert-butyldimethylsilyl chloride With tert-butoxide In tetrahydrofuran at 20℃;	85%

...Expand

: 695-06-7
hexan-4-olide

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 1360562-58-8
4-hydroxy-N-methoxy-N-methylhexanamide

Conditions

Conditions	Yield
With isopropylmagnesium chloride In tetrahydrofuran at -20 - -15℃; for 0.333333h; Inert atmosphere;	85%

: 695-06-7
hexan-4-olide

: 617-86-7
triethylsilane

: triethylsilyl 4-iodohexanoate

Conditions

Conditions	Yield
With 1,2-bis-(diphenylphosphino)ethane; methyl iodide; palladium(II) acetylacetonate at 80 - 90℃; for 12h;	82%

: 695-06-7
hexan-4-olide

: 1117-74-4
4-oxohexanoic acid

Conditions

Conditions	Yield
Stage #1: hexan-4-olide With sodium hydroxide In ethanol Stage #2: With sodium hypochlorite In aq. phosphate buffer at 20℃; for 20h;	81%
With tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃;	72%
With sodium hydroxide; bromine; magnesium sulfate
Multi-step reaction with 2 steps 1: NaOH / ethanol 2: NaOCl / aq. phosphate buffer / 20 h / 20 °C / pH 6.6 View Scheme

: 695-06-7
hexan-4-olide

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: N-(benzyloxy)-4-hydroxyhexanamide

Conditions

Conditions	Yield
Stage #1: O-benzylhydoxylamine hydrochloride With trimethylaluminum In tetrahydrofuran; toluene at 0 - 20℃; for 0.833333h; Stage #2: hexan-4-olide In tetrahydrofuran; toluene at 0℃; for 1.5h;	80%

: 695-06-7
hexan-4-olide

: 2393-23-9
4-methoxy-benzylamine

: 4-Hydroxyhexanoic acid 4-methoxybenzylamide

Conditions

Conditions	Yield
In neat (no solvent) at 80 - 85℃; for 16h; Heating; Large scale;	72.8%
In ethyl acetate

: 695-06-7
hexan-4-olide

: 75-03-6
ethyl iodide

: 14668-68-9
3,5-diethyl-dihydro-furan-2-one

Conditions

Conditions	Yield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide In tetrahydrofuran at -78℃;	68%
Stage #1: hexan-4-olide With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: ethyl iodide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;

4-Hexanolide Consensus Reports

Reported in EPA TSCA Inventory.

4-Hexanolide Specification

The 4-Hexanolide, with the CAS registry number 695-06-7, is also known as 5-Ethyldihydro-2(3H)-furanone. It belongs to the product categories of Heterocycles; Lactone Flavors. Its EINECS registry number is 211-778-8. This chemical's molecular formula is C₆H₁₀O₂ and molecular weight is 114.14. What's more, its IUPAC name is called 5-Ethyloxolan-2-one. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 4-Hexanolide are: (1)ACD/LogP: 0.413; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.41; (4)ACD/LogD (pH 7.4): 0.41; (5)ACD/BCF (pH 5.5): 1.21; (6)ACD/BCF (pH 7.4): 1.21; (7)ACD/KOC (pH 5.5): 39.98; (8)ACD/KOC (pH 7.4): 39.98; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.432; (14)Molar Refractivity: 29.509 cm³; (15)Molar Volume: 113.829 cm³; (16)Polarizability: 11.698×10^-24cm³; (17)Surface Tension: 29.002 dyne/cm; (18)Density: 1.003 g/cm³; (19)Flash Point: 79.338 °C; (20)Enthalpy of Vaporization: 45.124 kJ/mol; (21)Boiling Point: 214.904 °C at 760 mmHg; (22)Vapour Pressure: 0.152 mmHg at 25 °C.

Preparation of 4-Hexanolide: this chemical can be prepared by hept-6-en-3-ol. This reaction needs reagent cetyltrimethylammonium permanganate and solvent CHCl₃ at temperature of 25 °C. The reaction time is 4 hours. The yield is 69 %.

4-Hexanolide can be prepared by hept-6-en-3-ol.

Uses of 4-Hexanolide: (1) it is used as flavor; (2) it is used to produce other chemicals. For example, it can react with methanol to get 4-chloro-hexanoic acid methyl ester. The reaction occurs with reagent HCl and solvent methanol at temperature of 0 °C. The yield is 48 %.

4-Hexanolide can react with methanol to get 4-chloro-hexanoic acid methyl ester.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes. And it is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1OC(CC)CC1
(2) InChI: InChI=1S/C6H10O2/c1-2-5-3-4-6(7)8-5/h5H,2-4H2,1H3
(3) InChIKey: JBFHTYHTHYHCDJ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 794, 1979.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 794, 1979.

Product Name

4-Hexanolide

Synthetic route

4-Hexanolide Consensus Reports

4-Hexanolide Specification

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