Conditions | Yield |
---|---|
With hydrogen under 2250.23 Torr; for 15h; | 100% |
With CuZnCo-2.5 In ethanol at 200℃; for 0.5h; Temperature; Reagent/catalyst; Solvent; Autoclave; | 99.8% |
With hydrogen at 160℃; under 7500.75 Torr; for 1.5h; Catalytic behavior; Time; chemoselective reaction; | 98.1% |
Conditions | Yield |
---|---|
With ethanol at 210℃; for 5h; Reagent/catalyst; Autoclave; | A 99% B n/a |
Conditions | Yield |
---|---|
With MCM-36_M56 zeolite at 349.84℃; under 760.051 Torr; for 0.5h; | 98% |
With choline chloride; urea at 80℃; for 12h; Paal-Knorr Furan Synthesis; | 95% |
η-benzene-η-pentamethylcyclopentadienylrhodium(III) tetrafluoroborate at 200℃; for 5h; aldol condensation; | 90% |
Conditions | Yield |
---|---|
With tetradecane; hydrogen In ethanol at 200℃; under 22502.3 Torr; for 15h; Reagent/catalyst; Temperature; Pressure; | 97.6% |
With formic acid; sulfuric acid; palladium on carbon In tetrahydrofuran for 15h; Reflux; | |
With formic acid; sulfuric acid; palladium on activated charcoal In tetrahydrofuran for 15h; Reflux; |
Conditions | Yield |
---|---|
With hydrogen; pyrographite; N,N-dimethyl-formamide; palladium dichloride under 2585.81 Torr; for 1.75h; | 96% |
With methanol; Cu/Al2O3 at 240℃; for 6h; Reagent/catalyst; Sealed tube; | 72.8% |
With potassium tert-butylate; hydrazine hydrate In iso-butanol at 120℃; for 4h; Wolff-Kishner Reduction; | 62% |
5-methyl-2-furfuryl acetate
2,5-dimethylfuran
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; nickel dichloride at 0℃; for 3h; | 95% |
5-hydroxymethyl-2-furfuraldehyde
A
2-methylfuran
B
(2-furyl)methyl alcohol
C
2,5-dimethylfuran
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane at 180℃; under 11251.1 Torr; for 2h; Catalytic behavior; | A n/a B n/a C 93.4% |
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; N,N-dimethyl-formamide In toluene at 35 - 43℃; under 258.581 - 2585.81 Torr; Reagent/catalyst; Solvent; Pressure; Temperature; | 93% |
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; palladium/alumina; hydrogen In toluene at 30 - 35℃; under 2828.7 - 3345.86 Torr; for 2h; Reagent/catalyst; Solvent; | 84% |
With palladium on activated charcoal; hydrogen |
7-oxanorborn-5-ene-2,3-dicarboxylic anhydride
methyl iodide
2,5-dimethylfuran
Conditions | Yield |
---|---|
With aluminum (III) chloride at 120℃; for 2h; Reagent/catalyst; Temperature; | 93% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In diethyl ether under 1535.79 Torr; for 0.666667h; Solvent; | A n/a B 92% |
5-hydroxymethyl-tetrahydrofuran-2-carbaldehyde
A
2,5-dimethyltetrahydrofuran
B
tetrahydrofuran-2,5-dimethanol
C
2,5-dimethylfuran
D
2,5-hexanedione
E
5-methyltetrahydro-2-furaldehyde
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane at 180℃; under 9000.9 Torr; for 4h; Catalytic behavior; Overall yield = 100 %; | A 1.4% B 3.6% C 91.5% D 3.2% E n/a |
With hydrogen In 1,4-dioxane at 180℃; under 9000.9 Torr; for 4h; Catalytic behavior; Overall yield = 100 %; | A 9.5% B 4.9% C 80.1% D 3.4% E n/a |
2,5-bis(trimethylsilyloxy)hexa-2,4-diene
2,5-dimethylfuran
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 140℃; for 3.5h; | 90% |
Conditions | Yield |
---|---|
Amberlite IR-120 at 180℃; for 12h; | A 89% B 0.2% |
Amberlite IR-120 at 180℃; for 12h; Product distribution; various temperatures, also with Nafion-H; | A 89% B 0.2% |
Nafion-H at 180℃; for 12h; | A 30% B 3% |
5-hydroxymethyl-2-furfuraldehyde
A
2,5-dimethyltetrahydrofuran
B
2,5-dimethylfuran
C
n-hexan-2-ol
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane at 180℃; under 11251.1 Torr; for 15h; Temperature; Sealed tube; | A n/a B 88.5% C n/a |
Conditions | Yield |
---|---|
With hydrogen; 2 wt% Pd/C In tetrahydrofuran at 90℃; under 7757.43 Torr; for 2h; | 86% |
With methanol; sodium tetrahydroborate; nickel dichloride at 0℃; for 3h; | 67% |
With palladium on carbon; hydrogen In tetrahydrofuran at 90℃; under 2585.81 Torr; for 4h; | |
With hydrogen; Pd/C under 25858.1 Torr; Product distribution / selectivity; |
5-hydroxymethyl-2-furfuraldehyde
A
2,5-dimethyltetrahydrofuran
B
2,5-dimethylfuran
Conditions | Yield |
---|---|
With isopropyl alcohol In decane at 160℃; under 15001.5 Torr; for 8h; Reagent/catalyst; Temperature; Solvent; Pressure; Autoclave; Inert atmosphere; | A 8% B 84% |
With hydrogen In tetrahydrofuran at 220℃; under 11251.1 Torr; for 2.5h; Time; | A 6.4% B 67.5% |
With rhodium on carbon; hydrogen; 1-butyl-3-methylimidazolium chloride In tetrahydrofuran; water at 220℃; under 37503.8 Torr; for 5h; Solvent; Reagent/catalyst; Autoclave; | A 20% B 47% |
2-(chloromethyl)-5-(dibutoxymethyl)furan
2,5-dimethylfuran
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In pentane for 0.5h; | 82% |
With 5%-palladium/activated carbon; hydrogen In pentane under 1277.21 Torr; for 0.666667h; Solvent; | 93 %Chromat. |
2,5-bis-(hydroxymethyl)furan
A
2,5-dimethylfuran
B
5-Methylfurfural
C
2,5-diformylfurane
Conditions | Yield |
---|---|
With iodine at 60℃; for 10h; Inert atmosphere; Sealed tube; | A 5% B 80% C 6% |
5-hydroxymethyl-2-furfuraldehyde
A
2,5-dimethylfuran
B
5-Methylfurfural
C
2,5-bis-(hydroxymethyl)furan
E
2,2′-(1,2-ethanediyl)bis [5-methylfuran]
Conditions | Yield |
---|---|
With hydrogen In tetrahydrofuran at 130℃; under 7500.75 Torr; for 24h; Pressure; Temperature; Reagent/catalyst; Time; Autoclave; High pressure; | A 76% B n/a C n/a D n/a E n/a |
A
2,5-dimethylfuran
B
(E)-1,1,3,3-Tetrachlor-2,4-dineopentyl-1,3-disilacyclobutan
C
3,3-Dichlor-4-trichlorsilyl-6,6-dimethyl-3-silahept-1-en
Conditions | Yield |
---|---|
In neat (no solvent) at 170℃; for 72h; vacuum; Further byproducts given; | A n/a B n/a C n/a D 75% |
A
2,5-dimethylfuran
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; acetic acid In N,N-dimethyl-formamide at 20℃; under 1535.79 Torr; | A 74% B n/a |
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; acetic acid In N,N-dimethyl-formamide at 20℃; under 1535.79 Torr; | A 73% B n/a |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen; acetic acid under 1535.79 Torr; | A 72% B n/a |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tributylphosphine; perfluorinated resinsulfonic acid (Nafion-H type) at 130℃; for 5h; | 71% |
Conditions | Yield |
---|---|
With hydrogen; Al(OH)(2,2'-bipyridine-5,5'-dicarboxylic acid)0.81(PdCl2)0.48(OTf)0.38 at 150℃; under 15001.5 Torr; for 24h; | A 71% B 29% |
With awaruite; hydrogen at 160℃; under 7500.75 Torr; for 2h; Catalytic behavior; Time; chemoselective reaction; | A 15.7% B 19.8% |
With hydrogenchloride; hydrogen In tetrahydrofuran at 60℃; under 760.051 Torr; for 6h; Reagent/catalyst; Schlenk technique; | A 8 %Chromat. B 7 %Chromat. |
5-hydroxymethyl-tetrahydrofuran-2-carbaldehyde
A
2,5-dimethyltetrahydrofuran
B
tetrahydrofuran-2,5-dimethanol
C
2,5-dimethylfuran
D
2-hydroxymethyl-5-methylfuran
E
5-methyltetrahydro-2-furaldehyde
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane at 180℃; under 9000.9 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Overall yield = 100 %; | A 25.4% B 3.1% C 66.4% D 2.8% E n/a |
Conditions | Yield |
---|---|
With aluminum (III) chloride; phosphoric acid; 5 wt% ruthenium/carbon; sulfuric acid; hydrogen In N,N-dimethyl-formamide at 200℃; under 11251.1 Torr; for 12h; Reagent/catalyst; Autoclave; | 66.3% |
With palladium on activated charcoal; hydrogen; zinc(II) chloride In tetrahydrofuran; water at 150℃; under 6000.6 Torr; for 9.5h; | 19% |
Multi-step reaction with 2 steps 1: Amb-70; Sn-β / water; tetrahydrofuran; 2-methyltetrahydrofuran / 0.67 h / 130 °C 2: SnRu/C; hydrogen / water / 4 h / 200 °C View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid at 80℃; for 10h; Reagent/catalyst; Temperature; | 64% |
5-hydroxymethyl-2-furfuraldehyde
A
2,5-dimethylfuran
B
2-hydroxymethyl-5-methylfuran
Conditions | Yield |
---|---|
With hydrogen In tetrahydrofuran at 220℃; under 11251.1 Torr; for 2h; | A 62.3% B 9.3% |
With hydrogenchloride; palladium on activated charcoal; hydrogen In tetrahydrofuran at 60℃; under 760.051 Torr; for 12h; Reagent/catalyst; Schlenk technique; | |
With hydrogen In ethanol at 230℃; under 37503.8 Torr; for 6h; | A 85.9 %Chromat. B 10.6 %Chromat. |
Conditions | Yield |
---|---|
With water at 100℃; for 2h; | 100% |
With carbon dioxide In water at 150℃; under 30003 Torr; for 15h; Autoclave; | 95% |
With carbon dioxide In water at 150℃; under 30003 Torr; for 15h; Autoclave; | 95% |
2,5-dimethylfuran
mesoxalate de methyle
2-Hydroxy-2-(5-methyl-furan-2-ylmethyl)-malonic acid dimethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; under 6375510 Torr; for 24h; | 100% |
In dichloromethane at 25℃; under 7500600 Torr; for 20h; | 80% |
In dichloromethane at 25℃; under 7500600 Torr; | 80% |
2,5-dimethylfuran
α-chloroacetophenone benzoylhydrazone
1-benzoyl-4a,6-dimethyl-3-phenyl,1,4,4a,7a-tetrahydrofuro<2,3-e>pyridazine
Conditions | Yield |
---|---|
With sodium carbonate In dichloromethane for 12h; | 100% |
2,5-dimethylfuran
dimethyl acetylenedicarboxylate
dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 103℃; | 100% |
In dichloromethane under 7500600 Torr; for 20h; Ambient temperature; | 95% |
In 1,4-dioxane at 101℃; for 17.5h; | 81% |
2,5-dimethylfuran
dimethyl acetylenedicarboxylate
dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
Conditions | Yield |
---|---|
at 100℃; for 21h; | 100% |
at 100℃; for 2h; Sealed tube; | 78% |
In 1,4-dioxane at 100℃; for 24h; Diels-Alder reaction; | |
In toluene at 150℃; Diels-Alder reaction; Microwave irradiation; |
2,5-dimethylfuran
1,4-dimethyl-2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene
Conditions | Yield |
---|---|
With oxygen In chloroform at -60℃; | 100% |
With oxygen In dichloromethane Rate constant; | |
With oxygen In dichloromethane Rate constant; Mechanism; Irradiation; further furans and cyclopentadienes; |
2,5-dimethylfuran
2,5-dimethoxyphenyl triflate
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 25℃; | 100% |
Conditions | Yield |
---|---|
In acetonitrile at 20 - 40℃; for 0.583333h; Schlenk technique; Inert atmosphere; | 100% |
2,5-dimethylfuran
sodium 2-(4-methoxyphenyl)diazene-1-sulfonate
trifluoroacetic acid
Conditions | Yield |
---|---|
In acetonitrile at 20 - 40℃; for 0.583333h; Schlenk technique; Inert atmosphere; | 100% |
2,5-dimethylfuran
(Z)-hex-3-ene-2,5-dione
Conditions | Yield |
---|---|
With magnesium monoperoxyphthalate hexahydrate In ethanol; water for 0.25h; Ambient temperature; | 99% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -10 - 20℃; | 99% |
With monoperoxyphthalic acid magnesium salt hexahydrate In ethanol; water at 20℃; for 0.25h; Inert atmosphere; | 99% |
2,5-dimethylfuran
1,2,3,3-tetrachlorocyclopropene
2,3,4,4-tetrachloro-1,5-dimethyl-8-oxa-bicyclo-[3.2.1]octa-2,6-diene
Conditions | Yield |
---|---|
In benzene at 80℃; Diels-Alder cycloaddition; | 99% |
In toluene for 16h; Diels-Alder Reaction; Heating / reflux; | 95.9% |
In toluene for 16h; Heating / reflux; |
Conditions | Yield |
---|---|
With tin(IV) chloride; bis(1,5-cyclooctadiene)diiridium(I) dichloride at 90℃; for 0.166667h; | 99% |
With [Cp*Ir(SnCl3)2{SnCl2(H2O)2}] In 1,2-dichloro-ethane at 70℃; Schlenk technique; Inert atmosphere; regioselective reaction; | 96% |
With copper(ll) bromide In 1,2-dichloro-ethane at 85℃; for 3h; Friedel-Crafts Alkylation; | 85% |
2,5-dimethylfuran
bis(pinacol)diborane
2-(2,5-dimethylfuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether Inert atmosphere; Stage #2: 2,5-dimethylfuran In tert-butyl methyl ether at 80℃; for 0.0333333h; Inert atmosphere; Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
In toluene Diels-Alder Cycloaddition; Reflux; | 99% |
2,5-dimethylfuran
dimethyl acetylenedicarboxylate
diethyl 1,4-dimethyl-7-oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 100℃; for 24h; Diels-Alder Cycloaddition; Inert atmosphere; | 99% |
2,5-dimethylfuran
ferrocenyl(2-methylphenyl)methanol
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In 1,2-dichloro-ethane at 20℃; chemospecific reaction; | 99% |
Conditions | Yield |
---|---|
In dichloromethane for 20h; Ambient temperature; | 98% |
2,5-dimethylfuran
2,3,5,6-tetrabromo-p-xylene
6,7-dibromo-1,4,5,8-tetramethyl-1,4-dihydronaphthlene-1,4-endoxide
Conditions | Yield |
---|---|
With n-butyllithium In hexane; toluene at -78℃; for 2h; | 98% |
2,5-dimethylfuran
3,4-dibromo-1-methyl-2,5-dihydropyrrole-2,5-dione
2,6-dibromo-1,4,7-trimethyl-10-oxa-4-azatricyclo<5.2.1.02,6>dec-8-ene-3,5-dione
Conditions | Yield |
---|---|
at 70℃; for 18h; | 98% |
Conditions | Yield |
---|---|
With Hf/SBA-15(20) at 150℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere; | 98% |
With solid acid H form zeolite Y with 2.6 Si/Al catalyst In toluene at 150℃; under 3750.38 Torr; for 0.5h; Inert atmosphere; | 93% |
With Fe3O4atSiO2atCS-SO3H In methanol; water at 170℃; for 3h; Temperature; Solvent; Autoclave; | 79.9 %Chromat. |
Conditions | Yield |
---|---|
With hafnium tetrachloride In dichloromethane at -30℃; for 11h; | 97% |
Conditions | Yield |
---|---|
With P-containing zeolite Beta In n-heptane at 250℃; under 46504.7 Torr; Reagent/catalyst; Diels-Alder Cycloaddition; | 97% |
With benzoic acid anhydride In acetic acid at 280℃; under 63006.3 Torr; for 8h; Pressure; Reagent/catalyst; Solvent; Temperature; Time; | 92.3% |
With copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 270℃; under 26892.4 - 82745.9 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; | 91% |
2,5-dimethylfuran
1-(4-methylbenzenesulfonyl)-4-(4-fluorobenzene)-1H-1,2,3-triazole
1-(4-(4-fluorophenyl)-2-methyl-1-tosyl-1H-pyrrol-3-yl)propan-2-one
Conditions | Yield |
---|---|
With Rh2[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 In 1,2-dichloro-ethane at 70℃; for 6h; Inert atmosphere; | 97% |
2,5-dimethylfuran
α-bromomethyl p-nitrophenyl ketoxime
Conditions | Yield |
---|---|
With sodium carbonate In dichloromethane at 20℃; for 17.5h; | 97% |
2,5-dimethylfuran
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 16h; Diels-Alder Cycloaddition; | 97% |
2,5-dimethylfuran
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
1,4-dimethyl-1,4-dihydro-1,4-epoxynaphthalene
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 20℃; for 16h; Diels-Alder Cycloaddition; | 97% |
Molecular Structure of 2,5-Dimethyl furane (CAS NO.625-86-5):
IUPAC Name: 2,5-Dimethylfuran
Molecular Formula: C6H8O
Molecular Weight: 96.13
EINECS: 210-914-3
Melting Point: -62 °C
Index of Refraction: 1.45
Molar Refractivity: 28.2 cm3
Molar Volume: 104.7 cm3
Surface Tension: 25.9 dyne/cm
Density: 0.917 g/cm3
Flash Point: 29 °F
Enthalpy of Vaporization: 31.91 kJ/mol
Boiling Point: 93.1 °C at 760 mmHg
Vapour Pressure: 57.1 mmHg at 25 °C
storage temp.: Flammables area
Classification Code: Mutation data
Appearance: clear colorless to amber liquid
Canonical SMILES: CC1=CC=C(O1)C
InChI: InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
InChIKey: GSNUFIFRDBKVIE-UHFFFAOYSA-N
Product Categories: Furans; furnan Flavor; Building Blocks; Heterocyclic Building Blocks
Air & Water Reactions: Highly flammable, Insoluble in water
2,5-Dimethyl furane (CAS NO.625-86-5) is used as a pharmaceutical intermediate and potential biofuel and used for organic synthesis.
1. | dnr-bcs 190 µg/disc | DFSCDX Developments in Food Science. 13 (1986),353. | ||
2. | cyt-ham:ovr 8 mmol/L | CALEDQ Cancer Letters (Shannon, Ireland). 13 (1981),89. | ||
3. | ihl-rat LCLo:500 ppm/4H | JIHTAB Journal of Industrial Hygiene and Toxicology. 31 (1949),343. |
Reported in EPA TSCA Inventory.
Moderately toxic by inhalation. Mutation data reported. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Keep away from heat and open flame. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of 2,5-Dimethyl furane (CAS NO.625-86-5):
Hazard Codes: F,Xn
Risk Statements: 11-22
R11:Highly flammable.
R22:Harmful if swallowed.
Safety Statements: 16
S16:Keep away from sources of ignition.
RIDADR: UN 1993 3/PG 2
WGK Germany: 3
RTECS: LU0875000
F: 8
Hazard Note: Harmful/Flammable
HazardClass: 3
PackingGroup: II
2,5-Dimethyl furane (CAS NO.625-86-5), its Synonyms are 2,5-Dimethylfuran ; Furan, 2,5-dimethyl- ; 2.5-Dimethyl furan .
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