5-Hydroxy-4-methyl-2(5H)-furanone supplier

Name
5-HYDROXY-4-METHYL-2(5H)FURANONE
EINECS 609-869-6
CAS No. 40834-42-2
Article Data13
CAS DataBase
Density 1.35 g/cm³
Solubility
Melting Point
Formula C₅H₆O₃
Boiling Point 328.121 °C at 760 mmHg
Molecular Weight 114.101
Flash Point 163.168 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Hydroxy-3-methylbut-2-en-4-olide;4-Methyl-5-hydroxy-2(5H)-furanone;5-Hydroxy-4-methyl-5H-furan-2-one;5-hydroxy-4-methylfuran-2(5H)-one;4-Methyl-5-hydroxy-2(5H)-furanone;
PSA 46.53000
LogP -0.19210

Synthetic route

: 83803-81-0
ethyl (E/Z)-4,4-dimethoxy-3-methylbut-2-enoate

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

Conditions

Conditions	Yield
With hydrogenchloride; iodine for 3h; Heating;	100%

: C14H26O3Si

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

Conditions

Conditions	Yield
With amberlyst-15; water Ambient temperature;	81%

: 123-38-6
propionaldehyde

: 298-12-4
Glyoxilic acid

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

Conditions

Conditions	Yield
With morpholine; hydrogenchloride In water at 20℃; for 13h; Reflux;	76%
With morpholine In 1,4-dioxane; water
Stage #1: Glyoxilic acid With morpholine In n-heptane; water at 0 - 20℃; Stage #2: propionaldehyde In n-heptane; water at 20 - 45℃; Stage #3: With hydrogenchloride In n-heptane; water at 20℃;

: 123-38-6
propionaldehyde

: 563-96-2
2,2-dihydroxyacetic acid

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

Conditions

Conditions	Yield
With morpholin hydrochloride In 1,4-dioxane; water 1) RT, 1 h, 2) 24 h, reflux;	76%

: 616-02-4
citraconic acid anhydride

A: 931-23-7
5-Hydroxy-3-methyl-5H-furan-2-one

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

Conditions

Conditions	Yield
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -30 - -15℃; for 3h; Inert atmosphere;	A 7% B 60%

: 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

: 78920-07-7
γ-morpholinobutenolide

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

Conditions

Conditions	Yield
With hydrogenchloride for 0.25h; Heating; Yield given;

: 78920-13-5
2-ethoxy-3-methyl-2H-furan-5-one

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

Conditions

Conditions	Yield
With hydrogenchloride for 0.25h; Heating; Yield given;

: 26315-61-7
L-menthyl glyoxylate

: 51043-49-3
(E)-1-(N-morpholino)propene

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

B: 109745-72-4
(E)-3-Methyl-4-oxo-but-2-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Conditions

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid Multistep reaction. Yields of byproduct given;
With sulfuric acid; toluene-4-sulfonic acid Yield given. Multistep reaction;

...Expand

: 203131-19-5
4-methyl-2-(triisopropyl)silyloxy-furan

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / dimethyldioxirane / acetone; CH2Cl2 2: 81 percent / H2O, Amberlyst-15 / Ambient temperature View Scheme

: 4744-08-5
1,1-diethoxypropane

: 10024-89-2
morpholin hydrochloride

: 6000-59-5
glyoxalic acid monohydrate

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

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; aqueous sodium chloride; ethyl acetate

...Expand

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

BF4OEt3: BF4OEt3

: 62054-50-6
(Z)-3-Methyl-4-oxo-but-2-enoic acid ethyl ester

Conditions

Conditions	Yield
With sodium hydride	95%

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

: 108-98-5
thiophenol

: 4-methyl-5-(phenylthio)furan-2(5H)-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 80℃; for 15h;	90%

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

: 26487-92-3
3-(triphenylphosphoranylidene)butan-2-one

: 58661-11-3
4-Methyl-5-(1-methyl-2-oxo-propyl)-5H-furan-2-one

Conditions

Conditions	Yield
In toluene Heating;	85%

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

: 74-88-4
methyl iodide

: 96928-85-7
methyl (Z)-3-methyl-4-oxo-2-butenoate

Conditions

Conditions	Yield
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide	85%
With sodium hydride 1.) HMPA, 0 deg C, 1 h, 2.) 20 min; Yield given. Multistep reaction;

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

: 994-30-9
triethylsilyl chloride

: 958300-33-9
5-triethylsilyloxy-4-methyl-2(5H)-furanone

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1h;	82%

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

: 54709-94-3
3-methyl-5,6-diaza-2,4-cyclohexadien-1-one

Conditions

Conditions	Yield
With hydrazine In tetrahydrofuran at 20 - 60℃;	80%
With hydrazine In tetrahydrofuran at 20 - 60℃;	80%
Multi-step reaction with 4 steps 1: tetrahydrofuran / 4 h / Heating 2: conc. HCl / 0.25 h / Heating 3: HCl(g) / 12 h / Heating 4: 60 percent / H2N-NH2*H2O / aq. ethanol / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: HCl(g) / 12 h / Heating 2: 60 percent / H2N-NH2*H2O / aq. ethanol / 3 h / Heating View Scheme

: 55809-36-4
3-amino-5-tert-butylisoxazole

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

: 5-(5-tert-butyl-1,2-isoxazol-3-yl)amino-4-methyl-2,5-dihydrofuran-2-one

Conditions

Conditions	Yield
In toluene for 8h; Reflux;	71%

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

: 100-51-6
benzyl alcohol

: 5-(benzyloxy)-4-methylfuran-2(5H)-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane; toluene for 5h; Heating;	70%

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

: 100-46-9
benzylamine

: 42855-59-4
1-benzyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one

Conditions

Conditions	Yield
Stage #1: 5-hydroxy-4-methyl-5H-furan-2-one; benzylamine In isopropyl alcohol at 40℃; for 1h; Stage #2: With sodium tetrahydroborate; sodium hydroxide In water; isopropyl alcohol at 0 - 25℃; for 1.5h; Stage #3: With acetic acid at 50℃; for 16h; pH=7-8;	69%

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

: 1095823-39-4
5-chloro-4-(trifluoromethyl)pyridin-2-amine

: 5-(5-chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one

Conditions

Conditions	Yield
In toluene for 16h; Reflux;	68%

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

: 69739-34-0
t-butyldimethylsiyl triflate

: 958300-34-0
5-tert-butyldimethylsilyloxy-4-methyl-2(5H)-furanone

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 2h;	64%

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

: 545-06-2
trichloroacetonitrile

: 861899-14-1
3-methyl-5-oxo-2,5-dihydrofuran-2-yl 2,2,2-trichloroacetimidate

Conditions

Conditions	Yield
With sodium hydride In dichloromethane at 20℃; for 4h;	63%

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

: 2393-23-9
4-methoxy-benzylamine

: 1-(4-methoxybenzyl)-4-methyl-1,5-dihydro-2H-pyrrol-2-one

Conditions

Conditions	Yield
Stage #1: 5-hydroxy-4-methyl-5H-furan-2-one; 4-methoxy-benzylamine In isopropyl alcohol at 40℃; for 1h; Stage #2: With sodium tetrahydroborate; sodium hydroxide In water; isopropyl alcohol at 0 - 25℃; for 1.5h; Stage #3: With acetic acid In water; isopropyl alcohol at 50℃; for 16h; pH=7-8;	63%

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

: 4227-95-6
[13C]methyl iodide

: 4-methyl-5-(methyl-13C)furan-2(5H)-one

Conditions

Conditions	Yield
Stage #1: [13C]methyl iodide With magnesium In diethyl ether at 40℃; for 1h; Inert atmosphere; Stage #2: 5-hydroxy-4-methyl-5H-furan-2-one In diethyl ether at 0 - 20℃;	57%

: 108-05-4
vinyl acetate

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

: 180063-09-6
(-)-5-(R)-acetoxy-4-methyl-2(5H)-furanone

Conditions

Conditions	Yield
With lipase R immobilized on Hyflo Super Cell In diethyl ether for 240h; Ambient temperature;	52%

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

: 2216-51-5
(-)-menthol

A: 120262-97-7, 120263-06-1, 120263-07-2, 120262-96-6
5-menthyloxy-4-methyl-2<5H>-furanone

B: 120262-97-7
(5S)-5-(l-menthyloxy)-4-methyl-2(5H)-furanone

Conditions

Conditions	Yield
	A 39% B n/a
at 120℃; for 72h; Yield given. Yields of byproduct given;
at 120℃; for 72h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

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

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

: 4-methyl-5-cinnamyloxy-2(5H)-furanone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 24h; Heating;	34%

: 22391-29-3
(E)-5-(furan-3-yl)-2-methylpent-2-en-1-ol

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

: 83882-99-9
ursinanolide

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane for 72h; Ambient temperature;	27%

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

: 70143-03-2
Z-(3,7-dimethylocta-2,6-dienyl)diphenylphosphine oxide

: 70143-09-8
2Z,4Z,6Z-3,7,11-trimethyldideca-2,4,6,10-tetraenoic acid

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran for 3h;	10%

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

: 13303-62-3
E-(3,7-dimethylocta-2,6-dienyl)diphenylphosphine oxide

: 70143-08-7
2Z,4E,6E-3,7,11-trimethyldideca-2,4,6,10-tetraenoic acid

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran	7%

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

: 1067-74-9
Methyl diethylphosphonoacetate

: 3555-79-1
(2Z,4E)-5-methoxycarbonyl-3-methyl-2,4-petadienone acid

Conditions

Conditions	Yield
With sodium methylate In methanol; diethyl ether

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

: 57380-65-1
cyclohex-1-enylmethyl-triphenyl-phosphonium; bromide

: 41438-10-2
(2Z,4E)-5-Cyclohex-1-enyl-3-methyl-penta-2,4-dienoic acid

Conditions

Conditions	Yield
(i) PhLi, (ii) /BRN= 1561665/; Multistep reaction;

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

: 56013-01-5
triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide

: 14398-44-8
(2Z,4E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-2,4-pentadienoic acid

Conditions

Conditions	Yield
(i) PhLi, (ii) /BRN= 1561665/; Multistep reaction;

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

: 54168-84-2
trans-β-formyl crotonic acid

Conditions

Conditions	Yield
With sodium methylate In methanol

5-Hydroxy-4-methyl-2(5H)-furanone Specification

The 2(5H)-Furanone,5-hydroxy-4-methyl-, with the CAS registry number 40834-42-2, has the systematic name of 5-hydroxy-4-methylfuran-2(5H)-one. And the molecular formula of this chemical is C₅H₆O₃. It belongs to the product category of Intermediates of Isotretinoin.

The physical properties of 2(5H)-Furanone,5-hydroxy-4-methyl- are as following: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 2.513; (5)ACD/KOC (pH 7.4): 2.507; (6)#H bond acceptors: 3; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 1; (9)Polar Surface Area: 46.53 Å²; (10)Index of Refraction: 1.529; (11)Molar Refractivity: 26.081 cm³; (12)Molar Volume: 84.521 cm³; (13)Polarizability: 10.339×10^-24cm³; (14)Surface Tension: 50.188 dyne/cm; (15)Density: 1.35 g/cm³; (16)Flash Point: 163.168 °C; (17)Enthalpy of Vaporization: 66.111 kJ/mol; (18)Boiling Point: 328.121 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC1=CC(=O)OC1O
(2)InChI: InChI=1/C5H6O3/c1-3-2-4(6)8-5(3)7/h2,5,7H,1H3
(3)InChIKey: XRNPHZPFAWLRNJ-UHFFFAOYAH

Product Name

5-HYDROXY-4-METHYL-2(5H)FURANONE

Synthetic route

5-Hydroxy-4-methyl-2(5H)-furanone Specification

Related Products

Hot Products