Conditions | Yield |
---|---|
With carbon dioxide; palladium/alumina at 145℃; under 45004.5 Torr; for 6.5h; Green chemistry; | 99% |
With carbon dioxide; 5% Pd(II)/C(eggshell) at 250℃; under 112511 Torr; Supercritical conditions; | 98% |
With palladium nanoparticles deposited on porous SBA-15 In cyclohexane at 150℃; for 24h; Molecular sieve; | 96% |
2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>
A
furan
B
1-oxaspiro<4.4>non-3-en-2-one
Conditions | Yield |
---|---|
In tetrahydrofuran at 130℃; | A n/a B 98% |
A
furan
Conditions | Yield |
---|---|
at 120℃; for 0.25h; Irradiation; | A n/a B 98% |
A
furan
Conditions | Yield |
---|---|
at 120℃; for 0.25h; Irradiation; | A n/a B 98% |
A
furan
Conditions | Yield |
---|---|
at 140℃; for 0.166667h; Irradiation; | A n/a B 98% |
A
furan
Conditions | Yield |
---|---|
at 120℃; for 0.25h; Irradiation; | A n/a B 98% |
A
furan
Conditions | Yield |
---|---|
at 140℃; for 0.166667h; Irradiation; | A n/a B 98% |
2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>
A
furan
B
1-oxa-spiro[4.5]dec-3-en-2-one
Conditions | Yield |
---|---|
In tetrahydrofuran at 130℃; under 7 Torr; | A n/a B 97% |
Conditions | Yield |
---|---|
tetra-n-heptylammonium iodide; tributyltin iodide In para-xylene at 109 - 117℃; for 0.75h; | A 96.1% B n/a C n/a |
2-methoxyfuran
trans-Crotonaldehyde
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
furan
Conditions | Yield |
---|---|
In diethyl ether; chloroform | 95% |
Conditions | Yield |
---|---|
With n-butyllithium; deuteromethanol In tetrahydrofuran; cyclohexane at -65℃; | A 6% B 93% |
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; copper diacetate; silver nitrate; sodium hydroxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 12h; Autoclave; Green chemistry; | 91% |
Conditions | Yield |
---|---|
at 500℃; under 0.01 Torr; Irradiation; | A n/a B 90% |
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; copper diacetate; silver nitrate; sodium hydroxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 12h; Autoclave; Green chemistry; | 90% |
(1R,2S,5R,6S,7S)-5-(2'-oxo-1'-propyl)-4,10-dioxatricyclo<5.2.1.O2,6>dec-8-ene
A
furan
B
(R)-2-(2'-oxo-1'-propyl)-2,5-dihydrofuran
Conditions | Yield |
---|---|
at 500℃; under 0.01 Torr; flash termolyses, contact time = 50 ms; | A n/a B 82% |
2-Furan-2-yl-4-hydroxy-6-oxo-4-phenyl-cyclohexanecarboxylic acid ethyl ester
A
furan
B
ethyl 3-hydroxy-[1,1'-biphenyl]-4-carboxylate
Conditions | Yield |
---|---|
With perchloric acid In benzene for 10h; Heating; | A n/a B 82% |
(1R,2S,5R,6S,7S)-5-cyanomethyl-4,10-dioxatricyclo<5.2.1.O2,6>dec-8-ene
A
furan
B
(R)-2-cyanomethyl-2,5-dihydrofuran
Conditions | Yield |
---|---|
at 500℃; under 0.01 Torr; flash termolyses, contact time = 50 ms; | A n/a B 80% |
diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate
aniline
A
furan
Conditions | Yield |
---|---|
In neat (no solvent) at 90℃; for 6h; Solvent; Temperature; Schlenk technique; Green chemistry; | A n/a B 77% |
furfural
A
Tetrahydrofurfuryl alcohol
B
furan
C
2-methylfuran
D
(2-furyl)methyl alcohol
Conditions | Yield |
---|---|
With hydrogen In methanol at 119.84℃; under 7500.75 Torr; for 1h; Catalytic behavior; Solvent; Reagent/catalyst; Autoclave; | A 6.2% B 8.9% C 7.7% D 75.5% |
With hydrogen In isopropyl alcohol at 180℃; under 15001.5 Torr; for 5h; Kinetics; Catalytic behavior; Time; Autoclave; Sealed tube; | A 13% B 22% C 54% D 8% |
With hydrogen at 250℃; under 760.051 Torr; | A 10.2% B 13.5% C 38.6% D 19% |
Conditions | Yield |
---|---|
With hydrogen at 210℃; Catalytic behavior; Temperature; | A 24.5% B 75.4% |
With nickel supported catalyst In methanol; water at 260℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Inert atmosphere; Autoclave; | A 58% B 31% |
With hydrogen; palladium on activated charcoal at 200℃; Product distribution; other catalysts, other temperatures, different ratios of H2, other selectivity; |
Conditions | Yield |
---|---|
at 358℃; for 0.000833333h; Product distribution; Curie-point pyrolysis; | A 15.3% B 74% C 2% |
morpholine
diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate
A
furan
B
diethyl (Z)-2-(morpholino)-2-butenedioate
Conditions | Yield |
---|---|
In neat (no solvent) at 90℃; for 0.0166667h; Schlenk technique; Green chemistry; | A n/a B 73% |
Conditions | Yield |
---|---|
With hydrogen In methanol at 119.84℃; for 1h; Catalytic behavior; Solvent; Reagent/catalyst; Autoclave; | A 13.4% B 10.3% C 70.7% |
With hydrogen at 210℃; | A 56.6% B 11.5% C 16.2% |
With hydrogen In isopropyl alcohol at 240℃; under 18751.9 Torr; for 1h; Catalytic behavior; Temperature; | A 39% B 7.3% C 25.9% |
Conditions | Yield |
---|---|
With oxygen; palladium diacetate; copper (I) acetate at 40℃; for 20h; | 70% |
4-(3,6-Dihydro-[1,2]oxazin-2-yl)-benzoic acid methyl ester
A
furan
B
1-(4-(methyl carboxylate) phenyl) pyrrole
C
4-methoxycarbonyl aniline
Conditions | Yield |
---|---|
In methanol Irradiation; | A n/a B 70% C 24% |
diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate
4-phenyl-1-piperazine
A
furan
Conditions | Yield |
---|---|
In neat (no solvent) at 90℃; for 0.0166667h; Schlenk technique; Green chemistry; | A n/a B 70% |
Conditions | Yield |
---|---|
at 358℃; for 0.000833333h; Product distribution; Curie-point pyrolysis; | A 3.2% B 69.8% C 3.1% D 8.6% |
D-Mannose
A
furan
B
furfural
C
Glycolaldehyde
D
hydroxy-2-propanone
Conditions | Yield |
---|---|
at 358℃; for 0.000833333h; Product distribution; Curie-point pyrolysis; | A 2.2% B 63.4% C 18.4% D 7.2% |
furan
maleic anhydride
exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
Conditions | Yield |
---|---|
In neat (no solvent, solid phase) for 1h; Diels-Alder Cycloaddition; Milling; | 100% |
In toluene at 110℃; for 24h; Diels-Alder Cycloaddition; Reflux; stereospecific reaction; | 100% |
at 25℃; for 16h; Diels-Alder reaction; | 98% |
Conditions | Yield |
---|---|
With 3% Pd/C; hydrogen In isopropyl alcohol at 219.84℃; under 25858.1 Torr; for 5h; Inert atmosphere; | 100% |
With hydrogen; acetic acid In water at 39.84℃; for 2h; Inert atmosphere; | 98% |
With ruthenium; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; under 22502.3 Torr; for 36h; Autoclave; chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
In diethyl ether Diels-Alder reaction; | 100% |
In diethyl ether at 20℃; for 6h; Diels-Alder Cycloaddition; | 98% |
In toluene at 20℃; for 72h; | 97% |
Conditions | Yield |
---|---|
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere; Stage #2: cyclobutanone In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water | 100% |
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 4h; Inert atmosphere; Stage #2: cyclobutanone In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; | 82% |
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere; Stage #2: cyclobutanone In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere; | 71% |
furan
dimethyl diazomalonate
2-((Z)-4-Oxo-but-2-enylidene)-malonic acid dimethyl ester
Conditions | Yield |
---|---|
With rhodium(II) acetate at 20℃; for 96h; | 100% |
Conditions | Yield |
---|---|
With copper (I) trifluoromethane sulfonate benzene In benzene for 0.25h; Ambient temperature; | 100% |
With <(CF3SO3Cu)2PhH>; calcium carbonate In benzene for 0.25h; Ambient temperature; Yield given; |
furan
ethyl bromopyruvate tert-butoxycarbonylhydrazone
t-Butyl ethyl 1,4,4a,7a-tetrahydrofuro<3,2-c>pyridazine-1,3-dicarboxylate
Conditions | Yield |
---|---|
With sodium carbonate In dichloromethane for 16h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With zinc(II) iodide at 40℃; for 48h; | 100% |
With zinc(II) chloride at 20℃; for 16h; | 90% |
Stage #1: acrylonitrile With zinc(II) chloride at 20℃; for 0.166667h; Stage #2: furan at 20℃; for 14h; | 83% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In dichloromethane for 0.166667h; Ambient temperature; | 100% |
With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 20℃; for 0.5h; | 64% |
furan
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In dichloromethane Ambient temperature; | 100% |
furan
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In dichloromethane Ambient temperature; | 100% |
furan
methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate
Conditions | Yield |
---|---|
In tetrahydrofuran for 168h; Ambient temperature; | 100% |
furan
(phenyl)[2,4,5-tris(trimethylsilyl)phenyl]iodonium triflate
1,4-endoxy-1,4-dihydro-6,7-bis(trimethylsilyl)naphthalene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.333333h; | 100% |
With tetrabutyl ammonium fluoride; diisopropylamine In tetrahydrofuran; dichloromethane for 0.166667h; Ambient temperature; Yield given; | |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; | 600 mg |
furan
11-oxa-tricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-4-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 0℃; for 0.5h; | 100% |
furan
Conditions | Yield |
---|---|
In benzene Cycloaddition; UV-irradiation; | 100% |
furan
5,5,5',5'-Tetramethyl-5H,5'H-[3,3']bipyrazolyl
A
2,7-dimethyl-octa-2,6-dien-4-yne
B
(1S,5S,6S)-6-(4-Methyl-pent-3-en-1-ynyl)-2-oxa-bicyclo[3.1.0]hex-3-ene
Conditions | Yield |
---|---|
In various solvent(s) at 12℃; Irradiation; pyrex, Philips HPK 125; | A 100% B 68% C n/a |
Conditions | Yield |
---|---|
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane for 1h; Reflux; Inert atmosphere; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; hexane at 20℃; for 0.166667h; | 100% |
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane for 0.5h; Metallation; lithiation; Heating; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; hexane at 20℃; for 0.5h; Substitution; | 84% |
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 0℃; for 1h; Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.25h; | 56% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; cycloaddition; elimination; | 100% |
furan
3-methyl-11-oxatricyclo[6.2.1.02,7]undeca-2(7)3,5,9-tetraene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; cycloaddition; elimination; | 100% |
furan
1,4-dihydro-1,4-epoxy-6-methylnaphthalene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; cycloaddition; elimination; | 100% |
furan
2-azidoacrylic acid benzyl ester
Conditions | Yield |
---|---|
Stage #1: 2-azidoacrylic acid benzyl ester In toluene at 110℃; Stage #2: furan In toluene at 20℃; for 168h; Diels-Alder reaction; Further stages.; | 100% |
furan
(1S,4R)-bicyclo[2.2.1]heptan-2-one
Conditions | Yield |
---|---|
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: (1S,4R)-bicyclo[2.2.1]heptan-2-one In tetrahydrofuran; hexane at 20℃; for 6h; | 100% |
With n-butyllithium In tetrahydrofuran at 20℃; for 18h; | 100% |
furan
maleiimide
3,6-epoxy-1,2,3,6-tetrahydrophthalimide
Conditions | Yield |
---|---|
In diethyl ether Diels-Alder reaction; | 100% |
In diethyl ether at 100℃; for 8h; Autoclave; | 99% |
In diethyl ether at 100℃; Inert atmosphere; Sealed tube; | 99% |
Conditions | Yield |
---|---|
In chloroform at 38℃; for 120h; | 100% |
In chloroform at 35℃; for 336000h; Diels-Alder reaction; | 74% |
Stage #1: furan; 3-maleimidepropionic acid In chloroform Darkness; Heating; Stage #2: In methanol; ethyl acetate at 45℃; for 0.25h; | 65% |
Conditions | Yield |
---|---|
In hexane at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 5h; Stage #2: 8-Bromo-1-octene In tetrahydrofuran; hexane at -78 - 20℃; | 100% |
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 4h; Stage #2: 8-Bromo-1-octene In tetrahydrofuran; hexane at 20℃; Further stages.; |
furan
[Rh(H)(Ph)(η5-pentamethylcyclopentadienyl)(PMe3)]
(C5Me5)Rh(PMe3)(2-furanyl)H
Conditions | Yield |
---|---|
In hexane N2-atmosphere; stirring (60°C, 23 h); evapn. (vac.); | 100% |
Conditions | Yield |
---|---|
In hexane (N2); standard Schlenk technique; hexane and PEt3 were added via syringeto mixt. of Ru complex and ligand; mixt. was stirred at room temp. for 20 h; volatiles evapd. with oil diffusion pump; crystd. from hexane at -30°C; recrystd. (pentane); | 100% |
furan
10-(trimethylsilyl)phenanthren-9-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 40℃; for 16h; Inert atmosphere; | 100% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; | 81% |
furan
6-bromo-2,5,8-trimethoxy-4-methylquinoline
5-aza-8-methyl-6,9,10-Dimethoxy-1,4-dihydro-1,4-epoxyanthracene
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -75℃; for 3h; | 100% |
Molecular Structure:
Molecular Formula: C4H4O
Molecular Weight: 68.074
IUPAC Name: Furan
Synonyms of Furan (CAS NO.110-00-9): 1,4-Epoxy-1,3-butadiene ; 5-17-01-00291 (Beilstein Handbook Reference) ; AI3-24244 ; Axole ; BRN 0103221 ; CCRIS 3159 ; Divinylene oxide ; EINECS 203-727-3 ; Furfuran ; HSDB 89 ; NCI-C56202 ; Oxacyclopentadiene ; Oxole ; RCRA waste number U124 ; Tetrole ; Furan [UN2389] [Flammable liquid] ; UN2389
CAS NO: 110-00-9
Classification Code: Mutation data ; Reproductive Effect ; Tumor data
Melting point: -85.6 °C
Index of Refraction: 1.427
Molar Refractivity: 18.55 cm3
Molar Volume: 72.2 cm3
Surface Tension: 24.8 dyne/cm
Density: 0.942 g/cm3
Enthalpy of Vaporization: 27.1 kJ/mol
Boiling Point: 31.4 °C at 760 mmHg
Vapour Pressure: 605 mmHg at 25°C
Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system similar to benzene. Because of the aromaticity, the molecule is flat and lacks discrete double bonds. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system.
In 1780 by Carl Wilhelm Scheele, the first Furan (CAS NO.110-00-9) derivative to be described was 2-furoic acid. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Limpricht in 1870, although he called it tetraphenol.
Furan (CAS NO.110-00-9) is mainly used to produce large quantities of hot-box process core Binder.
Furan can be obtained from FURFURAL by oxidation and decarboxylation of the resulting furan-2-carboxylic acid, the FURFURAL being derived by destructive distillation of corn cobs in the presence of SULFURIC ACID.
the Feist-Benary synthesis is the organic synthesis of classic furan.
and there is a simple synthesis methods for furans is the reaction of 1,4-diketones with PHOSPHORUS PENTOXIDE in the Paal-Knorr Synthesis. It is interesting that the Thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 140mg/kg (140mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BLOOD: HEMORRHAGE | Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926. |
dog | LDLo | oral | 234mg/kg (234mg/kg) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: HEMORRHAGE | Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926. |
mouse | LC50 | inhalation | 120mg/m3/1H (120mg/m3) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979. |
mouse | LD50 | intraperitoneal | 7mg/kg (7mg/kg) | American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979. | |
rabbit | LDLo | oral | 234mg/kg (234mg/kg) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: HEMORRHAGE | Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926. |
rat | LC50 | inhalation | 3398ppm/1H (3398ppm) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Hazelton Laboratories, Reports. Vol. HLA468-102, Pg. 1987, |
rat | LD50 | intraperitoneal | 5200ug/kg (5.2mg/kg) | American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979. |
Hazard Codes of Furan (CAS NO.110-00-9): T,F+
Risk Statements: 45-12-19-20/22-38-48/22-52/53-68
R45: May cause cancer.
R12: Extremely flammable.
R19: May form explosive peroxides.
R20/22: Harmful by inhalation and if swallowed.
R38: Irritating to skin.
R48/22: Harmful: danger of serious damage to health by prolonged exposure if swallowed.
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R68: Possible risk of irreversible effects.
Safety Statements: 53-45-61
S53: Avoid exposure - obtain special instructions before use.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: OB3870000
F: 8-9-23
HazardClass: 3
PackingGroup: I
Behavior of Furan (CAS NO.110-00-9) is quite dissimilar to that of the more typical heterocyclic ethers such as tetrahydrofuran due to its aromaticity, .It is considerably more reactive than benzene in electrophilic substitution reactions, due to the electron-donating effects of the oxygen heteroatom. Examination of the resonance contributors shows the increased electron density of the ring, leading to increased rates of electrophilic substitution.
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