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(S)-(-)-5-Hydroxymethyl-2(5H)-furanone
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Name

(S)-(-)-5-Hydroxymethyl-2(5H)-furanone

 EINECS N/A
CAS No. 78508-96-0 Density 1.295 g/cm3
PSA 46.53000 LogP -0.53970
Solubility Slightly soluble in water. Melting Point 41-43 °C(lit.)
Formula C5H6O3 Boiling Point 334.754 °C at 760 mmHg
Molecular Weight 114.101 Flash Point 166.808 °C
Transport Information N/A Appearance N/A
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 78508-96-0 ((S)-(-)HYDROXYMETHYL-3(2H)-FURANONE) Hazard Symbols N/A
Synonyms

2(5H)-Furanone,5-(hydroxymethyl)-, (S)-;(5S)-Hydroxymethyl-5H-furan-2-one;(S)-(-)-5-(Hydroxymethyl)-2(5H)furanone;(S)-5-(Hydroxymethyl)furan-2(5H)-one;(S)-5-Hydroxy-2-penten-4-olide;l-Ranunculin aglycon;

Article Data 46

(S)-(-)-5-Hydroxymethyl-2(5H)-furanone Synthetic route

81703-94-8

methyl (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With sulfuric acid In methanol at 23℃; for 2h;97%
With camphor-10-sulfonic acid In methanol at 20℃;95%
With sulfuric acid In methanol at 20℃; for 2h;93%
With hydrogenchloride In water; acetonitrile for 2.75h; Product distribution; Further Variations:; Reagents;84%
With camphor-10-sulfonic acid at 25℃; for 3h;
36326-38-2, 64520-58-7, 91057-97-5, 91926-90-8, 104321-62-2, 124818-64-0, 128525-67-7, 128525-69-9, 104321-63-3

ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With sulfuric acid In methanol for 0.5h; Ambient temperature;95%
With sulfuric acid In methanol
91926-90-8

ethyl (Z)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With hydrogenchloride90%
With hydrogenchloride In ethanol for 2h; Ambient temperature;81%
With sulfuric acid
76236-32-3

2,3-dideoxy-5-O-(triphenylmethyl)-D-glycero-pent-2-enono-1,4-lactone

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Ambient temperature;90%
With hydrogenchloride; methanol
66601-82-9

methyl (S)-4,5-dihydroxy-4,5-O-isopropylidene-2-pentenoate

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With sulfuric acid In methanol at 25℃; for 1h;90%
With sulfuric acid; water In methanol at 20℃; for 2h; Cyclization;85%
37112-31-5

levoglucosenone

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With dihydrogen peroxide In water at 50℃; for 10h; Baeyer-Villiger Ketone Oxidation; Inert atmosphere; Cooling with ice;84%
Stage #1: levoglucosenone With Candida antarctica B lipase; dihydrogen peroxide In ethyl acetate at 40℃; for 8h; Baeyer-Villiger Ketone Oxidation; Green chemistry; Enzymatic reaction;
Stage #2: In 1,4-dioxane at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Green chemistry; regioselective reaction;		83%
With dihydrogen peroxide In water at 0 - 50℃; for 1h; Baeyer-Villiger Ketone Oxidation;76%
105122-15-4

(5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With water; acetic acid In tetrahydrofuran at 24℃; for 22h;82%
With acetic acid In tetrahydrofuran; water at 24℃; for 22h;82%
37112-31-5

levoglucosenone

A

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

B

85846-84-0

(-)-(S)-5-formyloxymethyloxol-3-en-2one

Conditions
ConditionsYield
With dihydrogen peroxide In water at 50℃; for 10h; Baeyer-Villiger Ketone Oxidation; Inert atmosphere; Cooling with ice; Large scale;A 71%
B n/a
With peracetic acid; dimethylsulfide; acetic acid 1.) RT, 2 d, 2.) 1 h; Multistep reaction. Title compound not separated from byproducts;
With Candida antarctica B lipase; dihydrogen peroxide In ethyl acetate at 40℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Baeyer-Villiger Ketone Oxidation; Green chemistry; Enzymatic reaction; regioselective reaction;
5336-08-3

D-Ribono-1,4-lactone

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
With methyltrioxorhenium(VII) at 170 - 180℃; for 15h; Sealed tube; Inert atmosphere;70%
Multi-step reaction with 2 steps
1: 1.) THF, 12 h, reflux, 2.) 7 d
2: 68 percent / 220 °C / 40 Torr
View Scheme
Multi-step reaction with 2 steps
1: tetrahydrofuran / 12 h / Heating
2: 68 percent / 220 °C / 40 Torr
View Scheme
With methyltrioxorhenium(VII) at 155℃; for 2h; Inert atmosphere;23.5 mg
78508-93-7

2,3-O-(ethoxymethylene)-D-ribonic acid γ-lactone

78508-96-0

(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions
ConditionsYield
at 220℃; under 40 Torr;68%

(S)-(-)-5-Hydroxymethyl-2(5H)-furanone Specification

The (S)-(-)-5-Hydroxymethyl-2(5H)-furanone, with the CAS registry number 78508-96-0, has the systematic name of (5S)-5-(hydroxymethyl)furan-2(5H)-one. It belongs to the following product categories: Chiral Reagent; Chiral Building Blocks; Furans; Heterocyclic Building Blocks. And the molecular formula of the chemical is C5H6O3. What's more, while dealing with this chemical, you should avoid contact with skin and eyes.

The characteristics of (S)-(-)-5-Hydroxymethyl-2(5H)-furanone are as followings: (1)ACD/LogP: -1.92; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 46.53 Å2; (7)Index of Refraction: 1.502; (8)Molar Refractivity: 26.015 cm3; (9)Molar Volume: 88.121 cm3; (10)Polarizability: 10.313×10-24cm3; (11)Surface Tension: 45.369 dyne/cm; (12)Density: 1.295 g/cm3; (13)Flash Point: 166.808 °C; (14)Enthalpy of Vaporization: 66.937 kJ/mol; (15)Boiling Point: 334.754 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C\1O[C@@H](/C=C/1)CO
(2)InChI: InChI=1/C5H6O3/c6-3-4-1-2-5(7)8-4/h1-2,4,6H,3H2/t4-/m0/s1
(3)InChIKey: AWNLUIGMHSSXHB-BYPYZUCNBO

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