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| CAS No.: | 78508-96-0 |
|---|---|
| Name: | (S)-(-)HYDROXYMETHYL-3(2H)-FURANONE |
| Article Data: | 46 |
| Cas Database | |
| Molecular Structure: | |
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| Formula: | C5H6O3 |
| Molecular Weight: | 114.101 |
| 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; |
| Density: | 1.295 g/cm3 |
| Melting Point: | 41-43 °C(lit.) |
| Boiling Point: | 334.754 °C at 760 mmHg |
| Flash Point: | 166.808 °C |
| Solubility: | Slightly soluble in water. |
| Safety: | 22-24/25 |
| PSA: | 46.53000 |
| LogP: | -0.53970 |
- 78510-19-7N-trans-Feruloyl-3-methoxytyramine
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- 78-51-3Tris(2-butoxyethyl) phosphate(TBEP)
- 78515-16-9Benzoic acid,5-formyl-2-methoxy-, methyl ester
- 78515-84-1Proper-myl (9CI)
- 78518-25-9D-glycero-D-gulo-Heptonic acid, 2-(4-methylphenyl)hydrazide
- 78521-39-8Hexanoic acid,6-[[(4-methylphenyl)sulfonyl]amino]-
- 785-30-8Benzamide,4-amino-N-(4-aminophenyl)-
- 78531-29-02-Propanamine,1,3-dimethoxy-
- 78531-59-6Ethanone,1-[4-(4-pentylcyclohexyl)phenyl]-, trans- (9CI)
- 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride | 90% |
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| at 220℃; under 40 Torr; | 68% |
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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