Product Name

  • Name

    Dihydrofuran-3(2H)-one

  • EINECS 805-925-0
  • CAS No. 22929-52-8
  • Article Data39
  • CAS DataBase
  • Density 1.128 g/cm3
  • Solubility
  • Melting Point
  • Formula C4H6O2
  • Boiling Point 151.1 °C at 760 mmHg
  • Molecular Weight 86.0904
  • Flash Point 56.3 °C
  • Transport Information
  • Appearance WHITE
  • Safety 16-26-36/37/39-23
  • Risk Codes 11-19-36/37/38-22
  • Molecular Structure Molecular Structure of 22929-52-8 (Dihydrofuran-3(2H)-one)
  • Hazard Symbols HarmfulXn
  • Synonyms 3-Oxotetrahydrofuran;Dihydro-3(2H)-furanone;Dihydrofuran-3-one;Oxolan-3-one;
  • PSA 26.30000
  • LogP -0.02420

Synthetic route

3-Hydroxytetrahydrofuran
453-20-3

3-Hydroxytetrahydrofuran

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;95%
methyl 4-oxotetrahydrofuran-3-carboxylate
57595-23-0

methyl 4-oxotetrahydrofuran-3-carboxylate

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 3h; Reagent/catalyst; Temperature;90.7%
In sulfuric acid6.8 g (79%)
ethyl tetrahydrofuran-3-one 4-carboxylate
89898-51-1

ethyl tetrahydrofuran-3-one 4-carboxylate

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 5h; Reagent/catalyst;82.3%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

A

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

RS(SR)-2,3-dibromotetrahydrofuran
20245-14-1, 52911-58-7, 138610-15-8

RS(SR)-2,3-dibromotetrahydrofuran

trans-3-bromo-2-hydroxytetrahydrofuran

trans-3-bromo-2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With water; oxygen; lithium bromide; copper(ll) bromide In tetrahydrofuran at 25℃; under 760.051 Torr;A 15%
B 75%
C 10%
...Expand
3-hydroxyfuran
29212-66-6

3-hydroxyfuran

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

Conditions
ConditionsYield
Stage #1: 3-hydroxyfuran With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In dichloromethane; water ice-water bath;
Stage #2: With sodium hypochlorite; sodium hydrogencarbonate In dichloromethane; water at 0 - 5℃; for 2.66667h;		67%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0 - 5℃; for 2.66667h; pH=9.5;67%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0 - 5℃; for 2.66667h; pH=9.5;67%
(+-)-tetrahydro-furan-3-ol

(+-)-tetrahydro-furan-3-ol

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

Conditions
ConditionsYield
With copper oxide-chromium oxide catalyst at 200 - 250℃;
With sodium dichromate; diethyl ether; sulfuric acid
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

A

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

B

(2S,3S)-3-chlorotetrahydrofuran-2-ol
1120-74-7, 29120-51-2, 29307-02-6

(2S,3S)-3-chlorotetrahydrofuran-2-ol

C

(2R,3R)-3-chlorotetrahydrofuran-2-ol

(2R,3R)-3-chlorotetrahydrofuran-2-ol

2-chloro-3-hydroxytetrahydrofuran

2-chloro-3-hydroxytetrahydrofuran

Conditions
ConditionsYield
With (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl; copper dichloride; palladium (II) ion Title compound not separated from byproducts;
...Expand
2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

Conditions
ConditionsYield
With dinitrogen monoxide In benzene at 220℃; for 12h; pressure;
1-butyn-4-ol
927-74-2

1-butyn-4-ol

tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

Conditions
ConditionsYield
With 5-bromo-2-methyl-pyridine-N-oxide; [BrettPhosAu]NTf2; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere; Darkness;42 %Spectr.
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

4-methoxybenzenesulfonyl hydrazide
1950-68-1

4-methoxybenzenesulfonyl hydrazide

N'-(dihydrofuran-3(2H)-ylidene)-4-methoxybenzene-sulfonohydrazide
1510865-64-1

N'-(dihydrofuran-3(2H)-ylidene)-4-methoxybenzene-sulfonohydrazide

Conditions
ConditionsYield
In methanol at 20℃; Schlenk technique;100%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

N'-(dihydrofuran-3(2H)-ylidene)-4-methylbenzene-sulfonohydrazide
1708-19-6

N'-(dihydrofuran-3(2H)-ylidene)-4-methylbenzene-sulfonohydrazide

Conditions
ConditionsYield
In methanol at 20℃; Schlenk technique;100%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

C26H37FN4O4

C26H37FN4O4

C30H43FN4O5

C30H43FN4O5

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 0.75h;99%
Stage #1: tetrahydrofuran-3-one; C26H37FN4O4 With acetic acid In dichloromethane at 20℃; for 0.75h;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

1-ethynyl-3-oxacyclopentanol
137344-86-6

1-ethynyl-3-oxacyclopentanol

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;97%
Stage #1: tetrahydrofuran-3-one; acetylenemagnesium bromide In tetrahydrofuran at 0 - 20℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran		57%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

nitromethane
75-52-5

nitromethane

3‑nitromethylidenetetrahydrofuran

3‑nitromethylidenetetrahydrofuran

Conditions
ConditionsYield
With sodium methylate In methanol at 20 - 30℃; for 6h; Reagent/catalyst; Temperature;96.7%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

sodium cyanide
773837-37-9

sodium cyanide

3-aminotetrahydrofuran-3-carbonitrile hydrochloride

3-aminotetrahydrofuran-3-carbonitrile hydrochloride

Conditions
ConditionsYield
Stage #1: tetrahydrofuran-3-one With ammonia; acetic acid In methanol at 20℃; for 0.166667h; Cooling with ice;
Stage #2: sodium cyanide In methanol at 20 - 50℃; for 2h;
Stage #3: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.25h;		96%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

tert-Butoxybis(dimethylamino)methane
5815-08-7

tert-Butoxybis(dimethylamino)methane

(E)-4-((dimethylamino)methylene)dihydrofuran-3(2H)-one

(E)-4-((dimethylamino)methylene)dihydrofuran-3(2H)-one

Conditions
ConditionsYield
In toluene at 20℃; for 18h;90%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

3-((trimethylsilyl)ethynyl)tetrahydrofuran-3-ol

3-((trimethylsilyl)ethynyl)tetrahydrofuran-3-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: tetrahydrofuran-3-one In tetrahydrofuran at -78 - 20℃; for 1.33333h;		89%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: tetrahydrofuran-3-one In tetrahydrofuran at -78 - 20℃; for 1.33333h; Inert atmosphere;		89%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

phenylacetylene
536-74-3

phenylacetylene

3-(phenylethynyl)tetrahydrofuran-3-ol

3-(phenylethynyl)tetrahydrofuran-3-ol

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: tetrahydrofuran-3-one In tetrahydrofuran; hexane at -78 - 20℃; for 2h;		89%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

potassium cyanide
151-50-8

potassium cyanide

3-cyano-3-dimethylamino-tetrahydrofurane
176445-75-3

3-cyano-3-dimethylamino-tetrahydrofurane

Conditions
ConditionsYield
In water Ambient temperature;88%
...Expand
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate

ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate

ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate

ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate

Conditions
ConditionsYield
Stage #1: tetrahydrofuran-3-one; ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate In methanol at 25℃; for 3h; Molecular sieve;
Stage #2: With sodium cyanoborohydride In methanol at 50℃; for 12h;		88%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

1,1,1,3,3,3-hexafluoropropan-2-yl 1-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate

1,1,1,3,3,3-hexafluoropropan-2-yl 1-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate

1,1,1,3,3,3-hexafluoropropan-2-yl 1-(7-(tetrahydrofuran-3-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate

1,1,1,3,3,3-hexafluoropropan-2-yl 1-(7-(tetrahydrofuran-3-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate

Conditions
ConditionsYield
Stage #1: tetrahydrofuran-3-one; 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate With triethylamine In 1,2-dichloro-ethane at 20℃; for 1.5h;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 4h;		86%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

nitromethane
75-52-5

nitromethane

C5H9NO4

C5H9NO4

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 18h;85.9%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

methanesulfonic acid
75-75-2

methanesulfonic acid

homoalylic alcohol
627-27-0

homoalylic alcohol

methanesulfonic acid 2,6-dioxaspiro[4.5]dec-9-yl ester
503551-88-0

methanesulfonic acid 2,6-dioxaspiro[4.5]dec-9-yl ester

Conditions
ConditionsYield
In dichloromethane at 23℃; Prins cyclization;85%
In dichloromethane at 25℃; for 16h;
...Expand
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

trans-3-((2-methyl-6-(5-methyl-6-(piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol

trans-3-((2-methyl-6-(5-methyl-6-(piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol

trans-3-((2-methyl-6-(5-methyl-6-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol

trans-3-((2-methyl-6-(5-methyl-6-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 6h;85%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

isoquinoline
119-65-3

isoquinoline

1-(4-oxotetrahydrofuran-2-yl)isoquinoline

1-(4-oxotetrahydrofuran-2-yl)isoquinoline

Conditions
ConditionsYield
With sodium persulfate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; trifluoroacetic acid In water at 23℃; for 24h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; regioselective reaction;83%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

ethylamine
75-04-7

ethylamine

N-ethyltetrahydrofuran-3-amine

N-ethyltetrahydrofuran-3-amine

Conditions
ConditionsYield
Stage #1: tetrahydrofuran-3-one; ethylamine With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 16h; Molecular sieve;
Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 2h;		83%
tetrahydrofuran-3-one
22929-52-8

tetrahydrofuran-3-one

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

3-(4-methoxyphenyl)tetrahydrofuran-3-ol

3-(4-methoxyphenyl)tetrahydrofuran-3-ol

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.416667h; Inert atmosphere;
Stage #2: tetrahydrofuran-3-one In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere;		82%

Dihydrofuran-3(2H)-one Specification

The Dihydrofuran-3(2H)-one, with CAS registry number 22929-52-8, belongs to the following product categories: (1)Carbonyl Compounds; (2)Heterocycles. It has the systematic name of dihydrofuran-3(2H)-one. And its IUPAC name is oxolan-3-one. And the chemical formula of this chemical is C4H6O2.

Physical properties of Dihydrofuran-3(2H)-one: (1)ACD/LogP: -1.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.14; (4)ACD/LogD (pH 7.4): -1.14; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.68; (8)ACD/KOC (pH 7.4): 5.68; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.442; (14)Molar Refractivity: 20.18 cm3; (15)Molar Volume: 76.2 cm3; (16)Polarizability: 8×10-24cm3; (17)Surface Tension: 35.4 dyne/cm; (18)Enthalpy of Vaporization: 38.8 kJ/mol; (19)Vapour Pressure: 3.72 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
The Dihydrofuran-3(2H)-one is highly flammable, so keep it away from sources of ignition. This chemical may form explosive peroxides. And it is also harmful if swallowed. When use it, wear suitable protective clothing, gloves and eye/face protection and do not breathe vapour. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1COCC1
(2)InChI: InChI=1/C4H6O2/c5-4-1-2-6-3-4/h1-3H2
(3)InChIKey: JLPJFSCQKHRSQR-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C4H6O2/c5-4-1-2-6-3-4/h1-3H2
(5)Std. InChIKey: JLPJFSCQKHRSQR-UHFFFAOYSA-N

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