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| CAS No.: | 67-47-0 |
|---|---|
| Name: | 5-Hydroxymethylfurfural |
| Article Data: | 788 |
| Cas Database | |
| Molecular Structure: | |
|
|
|
| Formula: | C6H6O3 |
| Molecular Weight: | 126.112 |
| Synonyms: | 2-Hydroxymethyl-5-furfural;5-(Hydroxymethyl)-2-furaldehyde;5-(Hydroxymethyl)-2-furancarbonal;5-(Hydroxymethyl)-2-furancarboxaldehyde;5-(Hydroxymethyl)-2-furfural;5-(Hydroxymethyl)-2-furfuraldehyde;5-(Hydroxymethyl)furfural;5-Hydroxymethyl-2-formylfuran;5-Hydroxymethylfuraldehyde;5-Hydroxymethylfuran-2-aldehyde;5-Hydroxymethylfurfuraldehyde;5-Hydroxymethylfurfurol;5-Oxymethylfurfurole;HMF;Hydroxymethylfurfural;Hydroxymethylfurfuralaldehyde;Hydroxymethylfurfuraldehyde;NSC 40738;5-Hydroxymethyl-2furfuraldehyde;5-Hydroxymethylfurfural;2-Furaldehyde,5-(hydroxymethyl)- (8CI);2-Formyl-5-hydroxymethylfuran; |
| EINECS: | 200-654-9 |
| Density: | 1.29 g/cm3 |
| Melting Point: | 30-34 °C |
| Boiling Point: | 291.5 °C at 760 mmHg |
| Flash Point: | 79.4 °C |
| Solubility: | Soluble in water, alcohol, ethyl acetate, acetone, dimethylformamide, benzene, ether and chloroform. |
| Appearance: | Beige coloured crystalline solid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38-52/53 |
| Safety: | 26-36-24/25 |
| PSA: | 50.44000 |
| LogP: | 0.58440 |
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- 67-47-0
5-hydroxymethyl-2-furfuraldehyde
| Conditions | Yield |
|---|---|
| With water at 25℃; for 1h; | 100% |
| With ethanol; silver nitrate | |
| With ethanol; water; barium carbonate | |
| With ethanol; silver(I) acetate at 80℃; |
| Conditions | Yield |
|---|---|
| With tetraethylammonium bromide; water at 80 - 100℃; for 0.416667h; | 100% |
| With tetraethylammonium bromide In water at 80 - 100℃; for 0.666667h; Inert atmosphere; | 100% |
| With sulfonated polyphenylene sulfide sulfone catalyst In dimethyl sulfoxide at 20 - 90℃; for 1.33333h; Temperature; | 100% |
| Conditions | Yield |
|---|---|
| With H-Beta catalyst In dimethyl sulfoxide at 119.84℃; for 3h; Solvent; Time; Temperature; Inert atmosphere; Green chemistry; | 100% |
| With sodium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water at 180℃; under 15001.5 Torr; for 1.75h; Inert atmosphere; | 98.2% |
| lanthanum(III) chloride In dimethyl sulfoxide at 120℃; for 2h; Dehydration; | 93% |
| Conditions | Yield |
|---|---|
| With formic acid; tetrabutylammomium bromide In ethanol; water at 270℃; under 112511 Torr; for 4h; Pressure; Reagent/catalyst; | 100% |
| With nickel doped 3D hybrids of reduced graphene oxide In tetrahydrofuran; water at 200℃; Solvent; Temperature; Reagent/catalyst; Microwave irradiation; Sealed tube; | 95% |
| With sodium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water at 175℃; under 15001.5 Torr; for 1.75h; Reagent/catalyst; Concentration; Solvent; Inert atmosphere; | 90.5% |
- 67-47-0
5-hydroxymethyl-2-furfuraldehyde
| Conditions | Yield |
|---|---|
| With Fe-based metal-organic framework Fe/C-S In ethanol at 100℃; under 750.075 Torr; for 2h; Inert atmosphere; | 99% |
| With 1-butyl-3-methylimidazolium chloride In ethanol at 50℃; for 2h; Solvent; | 97.4% |
| With Amberlyst-15 In dimethyl sulfoxide at 120℃; for 1.5h; Temperature; Time; Solvent; Reagent/catalyst; Concentration; Inert atmosphere; | 97.1% |
| Conditions | Yield |
|---|---|
| oxalic acid In dimethyl sulfoxide at 150℃; for 6h; Product distribution / selectivity; | 99% |
| With porous composite Al2SnO5 treated with phosphoric acid In N,N-dimethyl-formamide at 100℃; for 8h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 95% |
| With sulfonated carbon sphere solid acid catalyst In dimethyl sulfoxide at 160℃; for 1.5h; Reagent/catalyst; Solvent; Temperature; | 90% |
- 102390-86-3
5-(2-furaldehyde)methyl formate
- 67-47-0
5-hydroxymethyl-2-furfuraldehyde
| Conditions | Yield |
|---|---|
| With potassium carbonate In methanol at 50℃; | 94% |
- 67-47-0
5-hydroxymethyl-2-furfuraldehyde
| Conditions | Yield |
|---|---|
| With N-(4-sulphonic acid)butylpyridinium hydrogen sulphate In dimethyl sulfoxide at 150℃; for 2h; Reagent/catalyst; Solvent; Temperature; Large scale; | 93.2% |
- 67-47-0
5-hydroxymethyl-2-furfuraldehyde
| Conditions | Yield |
|---|---|
| With sulfuric acid In tetrahydrofuran at 200℃; Catalytic behavior; Reagent/catalyst; Temperature; | 99% |
| With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate; sodium chloride In tetrahydrofuran; water at 180℃; for 0.05h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Solvent; Autoclave; | 95% |
| With mesoscopically assembled sulfated zirconia nanoparticle In dimethyl sulfoxide at 110℃; for 2h; Reagent/catalyst; Time; Temperature; Autoclave; Green chemistry; | 91.9% |
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- 67-47-0
5-hydroxymethyl-2-furfuraldehyde
| Conditions | Yield |
|---|---|
| With phosphotungstic acid at 80℃; for 0.0833333h; Reagent/catalyst; Temperature; Solvent; Ionic liquid; Green chemistry; | 99% |
| With sodium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water at 175℃; under 15001.5 Torr; for 0.5h; Inert atmosphere; | 98.6% |
| With tin montmorillonite In tetrahydrofuran; dimethyl sulfoxide at 160℃; for 1h; | 78.1% |
| With tin (IV) chloride pentahydrate; 1-ethyl-3-methylimidazolium tetrafluoroborate at 100℃; for 3h; Ionic liquid; | 62% |
| With cerium(IV) phosphotungstate In water at 443℃; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave; |
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Chemistry
Molecular Structure of 5-Oxymethylfurfurole (CAS NO.67-47-0):
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IUPAC Name: 5-(Hydroxymethyl)furan-2-carbaldehyde
Molecular Formula: C6H6O3
Molecular Weight: 126.11
EINECS: 200-654-9
Melting Point: 28-34 °C(lit.)
storage temp.: 2-8 °C
Index of Refraction: 1.563
Molar Refractivity: 31.75 cm3
Molar Volume: 97.7 cm3
Surface Tension: 50 dyne/cm
Density: 1.29 g/cm3
Flash Point: 79.4 °C
Enthalpy of Vaporization: 56.07 kJ/mol
Boiling Point: 291.5 °C at 760 mmHg
Vapour Pressure: 0.000891 mmHg at 25 °C
Solubility: highly water-soluble
Sensitive: Air & Light Sensitive
Appearance: Beige Coloured Crystalline Solid
Classification Code: Mutation data; Tumor data
Product Categories: Aromatic Aldehydes & Derivatives (substituted); Aldehydes; Furans, Benzofurans & Dihydrobenzofurans; API intermediates; Detergents; furnan Flavor; Intermediates & Fine Chemicals; Mutagenesis Research Chemicals; Pharmaceuticals; Furans, Benzofurans & Dihydrobenzofurans
History
5-Oxymethylfurfurole (CAS NO.67-47-0) was studied by French chemist Louis Maillard in 1912 in studies on non-enzymatic reactions of glucose.
Uses
5-Oxymethylfurfurole (CAS NO.67-47-0) can be converted to 2,5-Dimethylfuran (DMF), which is a liquid biofuel that in certain ways is superior to ethanol. Oxidation of 5-Oxymethylfurfurole also gives 2,5-Furandicarboxylic acid, which has been proposed as a replacement terephthalic acid for the production of plastics. It has been found to bind specifically with intracellular sickle hemoglobin (HbS). Preliminary in vivo studies using transgenic sickle mice showed that orally administered it inhibits the formation of sickled cells in the blood.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| rat | LD50 | oral | 2500mg/kg (2500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | National Technical Information Service. Vol. OTS0544683, |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of 5-Oxymethylfurfurole (CAS NO.67-47-0):
Hazard Codes: 
Xi
Risk Statements: 36/37/38-52/53
R36/37/38:Irritating to eyes, respiratory system and skin.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: LT7031100
Specification
5-Oxymethylfurfurole (CAS NO.67-47-0), its Synonyms are 2-Hydroxymethyl-5-furfural ; 5-(Hyddroxymethyl)furfurole ; 5-(Hydroxymethyl)-2-furancarbonal ; 5-(Hydroxymethyl)-2-furancarboxaldehyde ; 5-(Hydroxymethyl)-2-furfural ; 5-(Hydroxymethyl)-2-furfuraldehyde ; 5-(Hydroxymethyl)furfural ; 5-Hydroxymethyl-2-formylfuran ; 5-Hydroxymethylfuraldehyde ; 5-Hydroxymethylfuran-2-aldehyde ; Hydroxymethylfurfural ; Hydroxymethylfurfuralaldehyde ; Hydroxymethylfurfuraldehyde ; Hydroxymethylfurfurole .