2(5H)-Furanone,3-methyl- supplier

Name
3-METHYL-2(5H)-FURANONE
EINECS
CAS No. 22122-36-7
Article Data52
CAS DataBase
Density 1.12 g/cm³
Solubility
Melting Point 72-73 °C(Solv: ethyl ether (60-29-7))
Formula C₅H₆O₂
Boiling Point 222.4 °C at 760 mmHg
Molecular Weight 98.1014
Flash Point 83.3 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Methyl-2-butenolide;2-Methylbut-2-en-4-olide;3-Methyl-2(5H)-furanone;4-Hydroxy-2-methyl-2-butenoic acid lactone;4-Hydroxy-2-methyl-2-butenoic acid g-lactone;2(5H)-Furanone, 3-methyl-;3-Methyl-2(5H)-furanone;3-Methylfuran-2(5H)-one;Furan-2(5H)-one, 3-methyl-;α-Methyl-γ-crotonolactone;
PSA 26.30000
LogP 0.48950

Synthetic route

: 201230-82-2
carbon monoxide

: 35761-83-2
3-iodo-but-2-ene-1-ol

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With potassium carbonate; hydrazine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 25℃; under 760 Torr; for 72h;	100%

: 18913-31-0
2,3-butadien-1-ol

: 201230-82-2
carbon monoxide

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; triethylamine In 1,4-dioxane at 100℃; under 7600 Torr; for 8h;	98%

: 850185-98-7
3-methyl-3-(4-trimethylsilylphenylselenyl)-3H-dihydrofuran-2-one

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With dihydrogen peroxide In dichloromethane at 0 - 20℃; for 0.75h;	96%

: 96-05-9
allyl methacrylate

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With C28H32Cl2N2ORu In toluene at 70℃; for 18h; Inert atmosphere;	91%

: 58588-90-2
α-bromomethyl-γ-butene lactone

A: 547-65-9
α-methylene-γ-butyrolactone

B: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With glucose dehydrogenase; D-glucose; NCR; nicotinamide adenine dinucleotide; NADH In dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction;	A 91% B 6%
With glucose dehydrogenase; D-glucose; Old Yellow Enzyme 3; nicotinamide adenine dinucleotide; NADH In dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction;	A 8% B 70%
With glucose dehydrogenase; D-glucose; Old Yellow Enzyme 3; nicotinamide adenine dinucleotide; NADH In dimethyl sulfoxide at 30℃; for 24h; Reagent/catalyst; Enzymatic reaction;
With glucose dehydrogenase; D-glucose; Old Yellow Enzyme 3; nicotinamide adenine dinucleotide; NADH In dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction;

: 547-65-9
α-methylene-γ-butyrolactone

: 691-37-2
4-Methyl-1-pentene

A: 22122-36-7
3-methyl-5H-furan-2-one

B: 3021-23-6
dihydro-3-(3-methylbutylidene)furan-2(3H)-one

Conditions

Conditions	Yield
With 2-chloro-1,3,2-benzodioxaborole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 14h;	A n/a B 87%
With chlorodicyclohexylphosphine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane-d2 at 40℃; for 14h;

...Expand

: 4-Bromomethyl-3-methyl-oxetan-2-one

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With silver nitrate In acetic acid Heating;	59%

: 88986-45-2
3-butenyl chloroformate

A: 547-65-9
α-methylene-γ-butyrolactone

B: 22122-36-7
3-methyl-5H-furan-2-one

C: 85120-17-8
bis(3-butenyl) carbonate

Conditions

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In xylene at 130℃; for 16h; Yield given. Yields of byproduct given;	A n/a B n/a C 49%
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In xylene at 130℃; for 16h; Yields of byproduct given;	A n/a B n/a C 49%

...Expand

: 2-chloro-3-hydroxy-2-methyl-γ-butyrolacton

A: 22122-36-7
3-methyl-5H-furan-2-one

B: 87683-09-8
3-hydroxy-2-methyl-γ-butyrolacton

Conditions

Conditions	Yield
With zinc In acetic acid for 0.5h;	A 45% B 36%

: 616-02-4
citraconic acid anhydride

A: 40834-42-2
5-hydroxy-4-methyl-5H-furan-2-one

B: 6124-79-4
4-methyl-2(5H)-furanone

C: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran THF, 0 deg C, 45 min; room temperature, 45 min;	A 5% B 43% C 5%

...Expand

: 78429-08-0
5-Benzenesulfinyl-3-methyl-dihydro-furan-2-one

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With pyridine for 3h; Heating;	27%

: 849585-22-4
LACTIC ACID

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
In water at 380℃; under 300030 Torr; for 0.0125h; Time;	23%

: 616-02-4
citraconic acid anhydride

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 6h;	15%
Stage #1: citraconic acid anhydride With N-cyclohexyl-cyclohexanamine In methanol at -15 - 20℃; for 3.5h; Stage #2: With carbonochloridic acid, butyl ester In dichloromethane at -12℃; for 12h; Stage #3: With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 3h; Further stages.;

: 1192-42-3
4,5-dihydro-3-hydroxy-3-methyl-2(3H)-furanone

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With phosphorus pentoxide
Multi-step reaction with 2 steps 1: pyridine, phosphorus tribromide / CHCl3 / 6 h / 0 °C 2: 80 percent / DBN / toluene / 0.5 h / Heating View Scheme

: 616-02-4
citraconic acid anhydride

A: 6124-79-4
4-methyl-2(5H)-furanone

B: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With sodium tetrahydroborate Yield given. Yields of byproduct given;
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Yield given. Yields of byproduct given;
With L-Selectride In tetrahydrofuran at -78 - 22℃; for 48h; Yield given. Yields of byproduct given;

: 88986-45-2
3-butenyl chloroformate

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 87532-06-7
α-methyl-γ-butyrolactone trimethylsilyl ketene acetal

A: 547-65-9
α-methylene-γ-butyrolactone

B: 22122-36-7
3-methyl-5H-furan-2-one

C: 1679-47-6
3-methyltetrahydro-2-furanone

Conditions

Conditions	Yield
With triethylamine hydrofluoride; lithium tert-butoxide CH2Cl2; Yield given. Multistep reaction. Yields of byproduct given;
With lead(IV) acetate; triethylamine hydrofluoride C2H2Cl2; Yield given. Multistep reaction. Yields of byproduct given;
With triethylamine hydrofluoride; lithium tert-butoxide C2H2Cl2; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 72017-07-3
α-Methyl-α-(phenylthio)-γ-butyrolactone

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With sodium periodate 1) aq. methanol, r.t.; 2) toluene, reflux, 0.5 h; Yield given. Multistep reaction;

: 4-Benzenesulfonyl-3-methyl-dihydro-furan-2-one

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 1h; Yield given;

: 80350-42-1
ethyl 4-acetoxy-4-chloro-2-hydroxy-2-methylbutanoate

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 4h; Heating;

: 85030-54-2
Acetic acid (E)-1-acetoxy-3-methyl-4-oxo-but-2-enyl ester

: 22122-36-7
3-methyl-5H-furan-2-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid Heating;

: 22122-36-7
3-methyl-5H-furan-2-one

: 59488-94-7
2-bromo-4-methyl-2H-furan-5-one

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 78℃; for 1.5h;	100%
With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane for 3h; Reflux; Dean-Stark;	68%
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 8h; Heating;	0.330 g

: 22122-36-7
3-methyl-5H-furan-2-one

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 176041-42-2
triisopropyl((3-methylfuran-2-yl)oxy)silane

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	99%
With triethylamine In dichloromethane at 20℃; for 1.5h;	99%
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	95%

: 22122-36-7
3-methyl-5H-furan-2-one

: 507-09-5
thioacetic acid

: cis-4-acetylthio-3-methyl-4,5-dihydro-2(3H)-furanone

Conditions

Conditions	Yield
With triethylamine at 50℃; for 72h;	95%

: 22122-36-7
3-methyl-5H-furan-2-one

: 2937-50-0
Allyl chloroformate

: 1402611-71-5
3-methylfuran-2-yl prop-2-en-1-yl carbonate

Conditions

Conditions	Yield
Stage #1: 3-methyl-5H-furan-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -60℃; Inert atmosphere; Stage #2: Allyl chloroformate In tetrahydrofuran Inert atmosphere;	94%
Stage #1: 3-methyl-5H-furan-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -60℃; Inert atmosphere; Stage #2: Allyl chloroformate In tetrahydrofuran at -60℃; for 0.333333h; Inert atmosphere;	92%

: 22122-36-7
3-methyl-5H-furan-2-one

: 3,4-dibromo-3-methyldihydrofuran-2-one

Conditions

Conditions	Yield
With bromine In dichloromethane at -10℃; for 2h;	93%

: 22122-36-7
3-methyl-5H-furan-2-one

: 2483-57-0
methyl 2-nitroacetate

: ((3R,4S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-nitro-acetic acid methyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 60℃; for 12h; Michael addition;	91%

: 98-91-9
thiobenzoic acid

: 22122-36-7
3-methyl-5H-furan-2-one

: cis-4-benzoylthio-3-methyl-4,5-dihydro-2(3H)-furanone

Conditions

Conditions	Yield
With triethylamine at 50℃; for 48h;	90%

: 22122-36-7
3-methyl-5H-furan-2-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 131497-06-8
tert-butyl(dimethyl)[(3-methylfuran-2-yl)oxy]silane

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 0℃; for 3h;	88.5%
With triethylamine In dichloromethane at 0 - 23℃; for 21h;	86%
Silylation;

: 4064-87-3
2,2-dimethyl-5-nitro-1,3-dioxane

: 22122-36-7
3-methyl-5H-furan-2-one

: trans-4-(2,2-dimethyl-5-nitro-1,3-dioxan-5-yl)-dihydro-3-methyl-2(3H)-furanone

Conditions

Conditions	Yield
With 1,1,3,3-tetramethylguanidine In acetonitrile at 17℃; for 48h;	85%

: 22122-36-7
3-methyl-5H-furan-2-one

: 79-46-9
2-nitropropane

: trans-3-methyldihydro-4-<2-(2-nitropropyl)>-2(3H)-furanone

Conditions

Conditions	Yield
With 1,1,3,3-tetramethylguanidine at 17℃; for 48h;	85%

: 22122-36-7
3-methyl-5H-furan-2-one

: 459-57-4
4-fluorobenzaldehyde

: (5S)-5-((R)-hydroxy(4-fluorophenyl)methyl)-3-methylfuran-2(5H)-one

Conditions

Conditions	Yield
Stage #1: 3-methyl-5H-furan-2-one; 4-fluorobenzaldehyde With N,O-bis-(trimethylsilyl)-acetamide; N-(3',5'-di-tert-butylbenzyl)quininium bromide; sodium 4-methoxyphenolate In tetrahydrofuran at -78℃; for 5h; Aldol Addition; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; enantioselective reaction;	82%

Yield

Stage #1: 3-methyl-5H-furan-2-one; 4-fluorobenzaldehyde With N,O-bis-(trimethylsilyl)-acetamide; N-(3',5'-di-tert-butylbenzyl)quininium bromide; sodium 4-methoxyphenolate In tetrahydrofuran at -78℃; for 5h; Aldol Addition; Inert atmosphere; Schlenk technique;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; enantioselective reaction;

82%

: 79-24-3
Nitroethane

: 22122-36-7
3-methyl-5H-furan-2-one

: (3R,4S)-3-Methyl-4-(1-nitro-ethyl)-dihydro-furan-2-one

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 24h; Michael addition;	78%

: 22122-36-7
3-methyl-5H-furan-2-one

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 61550-03-6
2-trimethylsilyloxy-3-methylfurane

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	78%
With triethylamine In dichloromethane at 20℃; for 1.5h; Cooling with ice; Inert atmosphere;	78%

: 22122-36-7
3-methyl-5H-furan-2-one

: (6S,7R,8S)-8-triisopropylsilyloxy-1-azabicyclo[5.3.0]decane-6-carbaldehyde

: (6S,7R,8S)-6-{[(1S)-hydroxy-(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]methyl}-8-triisopropylsilyloxy-1-azabicyclo[5.3.0]decane

Conditions

Conditions	Yield
Stage #1: 3-methyl-5H-furan-2-one With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: (6S,7R,8S)-8-triisopropylsilyloxy-1-azabicyclo[5.3.0]decane-6-carbaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; diastereoselective reaction;	78%

: 22122-36-7
3-methyl-5H-furan-2-one

: 121625-00-1
3,6-dimethoxyl-2-methylbenzaldehyde

: C15H18O5

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In chloroform for 0.5h; Reagent/catalyst; Inert atmosphere; UV-irradiation;	78%

: 54911-85-2
4-tetrahydropyranyloxybutanal

: 22122-36-7
3-methyl-5H-furan-2-one

: 1038587-97-1
5-[1-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-3-methylfuran-2-(5H)-one

Conditions

Conditions	Yield
Stage #1: 3-methyl-5H-furan-2-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 4-tetrahydropyranyloxybutanal In tetrahydrofuran at -78 - 20℃; for 2h; Further stages.;	76%

: 22122-36-7
3-methyl-5H-furan-2-one

: 104-88-1
4-chlorobenzaldehyde

: (5S)-5-((R)-hydroxy(4-chlorophenyl)methyl)-3-methylfuran-2(5H)-one

Conditions

Conditions	Yield
Stage #1: 3-methyl-5H-furan-2-one; 4-chlorobenzaldehyde With N,O-bis-(trimethylsilyl)-acetamide; N-(3',5'-di-tert-butylbenzyl)quininium bromide; sodium 4-methoxyphenolate In tetrahydrofuran at -78℃; for 5h; Aldol Addition; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; enantioselective reaction;	75%

Yield

Stage #1: 3-methyl-5H-furan-2-one; 4-chlorobenzaldehyde With N,O-bis-(trimethylsilyl)-acetamide; N-(3',5'-di-tert-butylbenzyl)quininium bromide; sodium 4-methoxyphenolate In tetrahydrofuran at -78℃; for 5h; Aldol Addition; Inert atmosphere; Schlenk technique;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; enantioselective reaction;

75%

2(5H)-Furanone,3-methyl- Specification

The 2(5H)-Furanone,3-methyl-, with the CAS registry number 22122-36-7-6, has the systematic name of 3-methylfuran-2(5H)-one. It belongs to the following product categories: Building Blocks; Furans; Heterocyclic Building Blocks. The molecular formula of this chemical is C₅H₆O₂.

The physical properties of 2(5H)-Furanone,3-methyl- are as following: (1)ACD/LogP: -0.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.25; (4)ACD/LogD (pH 7.4): -0.25; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 17.51; (8)ACD/KOC (pH 7.4): 17.51; (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: 1.471; (14)Molar Refractivity: 24.49 cm³; (15)Molar Volume: 87.5 cm³; (16)Polarizability: 9.7×10^-24cm³; (17)Surface Tension: 33.1 dyne/cm; (18)Density: 1.12 g/cm³; (19)Flash Point: 83.3 °C; (20)Enthalpy of Vaporization: 45.89 kJ/mol; (21)Boiling Point: 222.4 °C at 760 mmHg; (22)Vapour Pressure: 0.102 mmHg at 25°C.

Uses of 2(5H)-Furanone,3-methyl-: It can react with 2-nitro-propane to produce trans-3-methyldihydro-4-[2-(2-nitropropyl)]-2(3H)-furanone. This reaction will need reagent tetramethylguanidine (TMG). The reaction time is 2 days with temperature of 17°C, and the yield is about 85%.

2(5H)-Furanone,3-methyl- can react with 2-nitro-propane to produce trans-3-methyldihydro-4-[2-(2-nitropropyl)]-2(3H)-furanone

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting 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=C\1OC/C=C/1C
(2)InChI: InChI=1/C5H6O2/c1-4-2-3-7-5(4)6/h2H,3H2,1H3
(3)InChIKey: VGHBEMPMIVEGJP-UHFFFAOYAW

Product Name

3-METHYL-2(5H)-FURANONE

Synthetic route

2(5H)-Furanone,3-methyl- Specification

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