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FURAN = FURFURAN
CAS Number: 110-00-9
EC Number: 203-727-3
MDL number: MFCD00003222
Empirical Formula: C4H4O
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen.
The class of compounds containing such rings is also referred to as furans.
Chemical compounds containing such rings are also referred to as furans.
Furan is a colorless, highly volatile liquid with a boiling point close to room temperature.
Furan is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water.
Furan's odor is "strong, ethereal; chloroform-like".
Furan or furfuran is a heterocyclic aromatic organic compound.
Furan is a colorless, volatile, liquid.
Furan is aromatic because Furan obeys the 4n+2 electron system rule.
Furan is a clear, colorless, flammable liquid cyclic ether with an ethereal odor.
Furan appears as a clear colorless liquid with a strong odor.
Flash point below 32°F.
Less dense than water and insoluble in water.
Vapors heavier than air.
Furan is a monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O.
Furan is a mancude organic heteromonocyclic parent, a member of furans and a monocyclic heteroarene.
Furan is a volatile (boiling point = 31.4°C) cyclic ether found in cigarette smoke.
Among furan derivatives, 2-furaldehyde (furfural) and 5-hydroxymethylfurfural (HMF) constitute the main degradation compounds generated from pentoses and hexoses degradation, respectively.
The concentration of these compounds depends mainly on the conditions employed for pretreatment.
Thus, those pretreatments which employ acids as hydrolytic agents and utilize high temperature and time to reaction will produce furfural and HMF at higher levels.
Furan appears as a clear colorless liquid with a strong odor.
Colorless liquid with an ethereal odor; darkens on exposure to light and air.
Furan, any of a class of organic compounds of the heterocyclic aromatic series characterized by a ring structure composed of one oxygen atom and four carbon atoms.
The simplest member of the furan family is furan itself, a colourless, volatile, and somewhat toxic liquid that boils at 31.36° C (88.45° F).
Furan is usually converted by hydrogenation to tetrahydrofuran, which is used as a solvent and for production of adipic acid and hexamethylenediamine, the raw materials for nylon-6,6.
Several other members of the furan family are produced on a large scale for use as solvents and chemical raw materials.
The first furan compound discovered was pyromucic acid (2-furoic acid), prepared in 1780.
The aldehyde furfural, used as a solvent in petroleum refining, is manufactured from corn cobs and oat hulls by treatment with acid.
Many sugars exist in molecular forms called furanoses, possessing the tetrahydrofuran ring system.
Important examples are provided by ribose and deoxyribose—which are present in the furanose form in nucleic acids, the heredity-controlling components of all living cells—and fructose.
Furan is a colorless, volatile liquid used in some chemical manufacturing industries.
Furan has occasionally been reported to be found in foods.
Furan has an important biological properties and pharmacological activity.
Furan belongs to the class of organic compounds known as heteroaromatic compounds.
Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
Furan is a member of the class of compounds known as furans.
These are molecules containing a heterocyclic organic group consisting of a five-membered aromatic ring with four carbon atoms and one oxygen.
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, furan is flat and lacks discrete double bonds.
Furan is a colourless, highly volatile liquid with a boiling point close to room temperature (31 °C).
Furan is soluble in common organic solvents, including alcohol, ether, and acetone, but is insoluble in water.
Furan has a strong ethereal odour.
Furan is found in heat-treated (e.g. cooked, roasted, baked, pasteurized, and sterilized) commercial foods and is produced through thermal degradation of natural food constituents.
The term "furans" is sometimes used interchangeably with "dioxins."
Furan is not a dioxin-like compound.
In addition "furans" refers to a large class of compounds of widely varying structures including, for example, nitrofurans.
Furan is a colourless, volatile organic compound that is used in some chemical manufacturing industries and may also be found in low levels in some foods, most notably in foods that undergo thermal treatment such as canning or jarring.
Furan, as well as methyl-substituted furan derivatives, 2-methylfuran and 3-methylfuran, can form in foods through multiple pathways that involve different naturally-present precursor compounds (e.g. polyunsaturated fatty acids, sugars, ascorbic acid) that undergo thermal degradation or chemical rearrangement during food processing.
The chemical "furan" is different from "furans".
"Furans" is an abbreviation of chlorinated dibenzofurans and are chemically related to a group of chemicals called dioxins.
Furan is a heterocyclic organic compound that has a pentagon-shaped aromatic ring consisting of four carbon atoms and one oxygen atom.
The molecular formula for furan is C4H4O.
Furan has a resonance structure within the carbon and oxygen atoms, and has one hydrogen atom bonded with each carbon atom.
Furan has an ethereal odor and has a clear, colorless appearance.
Furan is a volatile liquid, with a boiling point close to room temperature.
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom.
Chemical compounds containing such rings are also referred to as furans.
Furan is a colorless, highly volatile liquid with a boiling point close to room temperature.
Furan is soluble in common organic solvents, including alcohol, ether, and acetone, and is slightly soluble in water.
Furan's odor is "strong, ethereal; chloroform-like".
Furan is a naturally-occurring chemical that has been found at low levels in several food items.
Scientists believe that its origin in food is likely as a breakdown product from traditional heat treatment processes such as cooking and canning.
Furan is important to note that furan is not the same as “furans”, which refers to polychlorinated dibenzofurans, which are often considered together with the chemically similar dioxins.
Furan is a clear, colourless, and volatile organic compound with an ethereal odor.
Dioxins and furans have much different chemical structures compared to furan.
Furan is a colorless, odorless, highly volatile liquid that is not water-soluble and has a boiling point of 31 °C.
Whereas Furan naturally occurs in oils from conifers that contain resins.
Furan is a heterocyclic organic compound consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. Chemical compounds containing such rings are also called furans.
Furan is a colorless and highly volatile liquid with a boiling point close to room temperature.
Furan is soluble in common organic solvents such as alcohol, ether and acetone and slightly soluble in water.
Colorless liquid with chloroform odor.
Boiling point 32°C Insoluble in water, soluble in ethanol.
Polymerize with an inorganic acid to form a resin .
Furan is a 5-membered ring heterocyclic compound C4H4O , but the aromaticity is small.
Furan is obtained by alkali treatment of furfural.
Furan is a colorless liquid that turns brown on standing.
Furan has a boiling point of 32 ° C.
Furan is a heterocyclic compound of the gross formula C4H4O.
Furan is found in wood tar , but is produced industrially by decarbonylation of furfural (which in turn is made from sugar cane ) using a palladium catalyst.
USES and APPLICATIONS of FURAN:
-Furan is used as a starting point for other speciality chemicals.
-Furan is used as an intermediate in the production of tetrahydrofuran, pyrrole and thiophene.
-Furan is used in the production of resins and lacquers, agrochemicals, and pharmaceuticals.
-Furan's iodinated lipophilic derivative is widely used in the treatment of ventricular and arterial fibrillation.
-Furan's derivatives are used as inhibitors of biofilm formation for several bacterial species, as well as possess quorum-sensing inhibitory activities.
-2-methylfuran and 2,5-dimethylfuran are used as lignocellulosic biofuels.
-Furan's resin is used to stop sand production in underground gas storage wells.
-Furan is a volatile compound that can form when food is heated.
-Furan undergo Diels-Alder reaction with arynes to give derivatives of dihydronaphthalenes which are useful intermediates in synthesis of other polycyclic aromatic compounds.
-Furan can be found in roasted coffee, instant coffee, and processed baby foods.
-Particularly high concentrations of furan are found in roasted food such as coffee and convenience foods that are subjected to high temperatures in closed containers.
-Furan is known in the chemical industry as an intermediate product in various kinds of organic synthesis.
-Furan is a food contaminant highly volatile and lipophilic, naturally present in food.
Furan is formed when food is heated at a high temperature in a closed container.
-Furan is mostly found in jarred food (as direct packing after processing impedes Furan's evaporation) and in roasted coffee beans, as well as in home-cooked food at a lesser extent.
-Furan is an organic compound used in chemical manufacturing and is sometimes found in low levels in some heat-treated beverages and foods such as coffee, and canned or jarred foods.
-Furan is a food chemical that is gaining attention.
Furan is most notably found in coffee, but Furan has also been detected in canned foods including soups, sauces, pasta and processed baby food.
-Furan is used in some chemical manufacturing and is also present in low levels in heat treated foods such as canned or jarred foods.
-Furan is used to manufacture the chemicals tetrahydrofuran, pyrrole, and thiophene.
-Furthermore, furan can be formed from many other ingredients, such as vitamin C, carbohydrates, unsaturated fatty acids, and carotenoids.
-Furan is also used to make some lacquers, as a solvent for resins, and to produce pharmaceuticals, agricultural chemicals, and stabilizers.
-In the food industry, furan also plays a significant role.
Like acrylamide, Furan is generated when food products are heated strongly during their production and/or processing.
-A colourless liquid, Furan is used in the synthesis of nylon.
-Depending on the composition of the food product, several different mechanisms of generation can be taken into consideration.
All of the relevant potential mechanisms are based on some sort of heating process, such as cooking or roasting.
The results of various studies indicate that the cleavage of amino acids and sugar during the heating process plays a significant role in furan formation.
-Furan can be present in a wide variety of food products, ranging from coffee, cocoa, dried fruit, and nuts, to various grain products.
-Particularly high amounts of furan have been identified in food products that are either roasted or heated in closed containers, such as canned goods and convenience food.
-In the case of convenience food, in general jars of baby food with pasta, meat, and vegetables display elevated levels of furan.
-Furan intake in children is mainly due to the consumption of roasted or puffed breakfast cereal products, dried fruit, and snacks such as popcorn.
-In adults, coffee consumption is the largest source.
-The substance is used, for example, for the preparation of pyrrole , thiophene and tetrahydrofuran , as a solvent and for several other purposes.
PRODUCTION of FURAN:
Industrially, furan is manufactured by the palladium-catalyzed decarbonylation of furfural, or by the copper-catalyzed oxidation of 1,3-butadiene.
MANUFACTURE of FURAN:
In the laboratory, furan can be obtained from furfural by oxidation to 2-furoic acid, followed by decarboxylation.
Furan can also be prepared directly by thermal decomposition of pentose-containing materials, and cellulosic solids, especially pine wood.
SYNTHESIS of FURAN:
The Feist–Benary synthesis is a classic way to synthesize furans, although many syntheses have been developed.
One of the simplest synthesis methods for furans is the reaction of 1,4-diketones with phosphorus pentoxide (P2O5) in the Paal–Knorr synthesis.
The thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products.
Many routes exist for the synthesis of substituted furans.
Due to its aromaticity, furan's behavior is quite dissimilar to that of the more typical heterocyclic ethers such as tetrahydrofuran.
Furan 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.
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 π system.
RESONANCE CONTRIBUTORS of FURAN:
Furan serves as a diene in Diels–Alder reactions with electron-deficient dienophiles such as ethyl (E)-3-nitroacrylate.
The reaction product is a mixture of isomers with preference for the endo isomer:
Furan Diels–Alder reaction with ethyl (E)-3-nitroacrylate
Diels-Alder reaction of furan with arynes provides corresponding derivatives of dihydronaphthalenes, which are useful intermediates in synthesis of other polycyclic aromatic compounds.
REACTION of FURAN WİTH A BENZYNE:
Hydrogenation of furans sequentially affords dihydrofurans and tetrahydrofuran.
In the Achmatowicz reaction, furans are converted to dihydropyran compounds.
Pyrrole can be prepared industrially by reacting furan and ammonia in the presence of solid acid catalysts, such as SiO2 and Al2O3.
HISTORY of FURAN:
The name "furan" comes from the Latin furfur, which means bran. (Furfural is produced from bran.)
The first furan derivative to be described was 2-furoic acid, by Carl Wilhelm Scheele in 1780.
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" (as if it were a four-carbon analog to phenol, C6H5OH).
ALTERNATIVE PARENTS of FURAN:
-Furans
-Oxacyclic compounds
-Organooxygen compounds
-Hydrocarbon derivatives
SUBSTITUENTS of FURAN:
-Heteroaromatic compound
-Furan
-Oxacycle
-Organic oxygen compound
-Hydrocarbon derivative
-Organooxygen compound
-Aromatic heteromonocyclic compound
PHYSICAL and CHEMICAL PROPERTIES of FURAN:
Appearance Form: liquid
Molecular Weight: 68.07
Color: light brown
Odor: No data available
Odor Threshold: No data available
pH: No data available
Melting point/freezing point:
Melting point/freezing point: -85,61 °C at 1.013 hPa - (ECHA)
Initial boiling point and boiling range: 32 °C at 1.011 hPa - lit.
Flash point: -36 °C - closed cup
Evaporation rate: No data available
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits:
Upper explosion limit: 14,3 %(V)
Lower explosion limit: 2,3 %(V)
Vapor pressure: 798 hPa at 25 °C
Vapor density: No data available
Density: 0,936 g/mL at 25 °C - lit.
Relative density: 0,94 at 20 °C
Water solubility: 10 g/l at 25 °C
Partition coefficient: n-octanol/water
log Pow: 1,34 - Bioaccumulation is not expected., (ECHA)
Autoignition temperature: No data available
Decomposition temperature: No data available
Viscosity
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Explosive properties: No data available
Oxidizing properties: none
Other safety information: No data available
Appearance: colorless liquid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity: 0.93700 to 0.94100 @ 20.00 °C.
Pounds per Gallon - (est).: 7.806 to 7.839
Refractive Index: 1.41900 to 1.42400 @ 20.00 °C.
Melting Point: -85.60 °C. @ 760.00 mm Hg
Boiling Point: 32.00 °C. @ 758.00 mm Hg
Boiling Point: 31.50 °C. @ 760.00 mm Hg
Vapor Pressure: 600.000000 mmHg @ 25.00 °C.
Vapor Density: 2.3 ( Air = 1 )
Flash Point: -32.00 °F. TCC ( -35.56 °C. )
logP (o/w): 1.340
Soluble in:
alcohol
water, 1.00E+04 mg/L @ 25 °C (exp)
Insoluble in:
water
FIRST AID MEASURES of FURAN:
-Description of first-aid measures:
No data available
-Indication of any immediate medical attention and special treatment needed:
No data available
ACCIDENTAL RELEASE MEASURES of FURAN:
-Environmental precautions:
No data available
-Methods and materials for containment and cleaning up:
No data available
FIRE FIGHTING MEASURES of FURAN:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Advice for firefighters:
No data available
-Further information:
No data available
EXPOSURE CONTROLS/PERSONAL PROTECTION of FURAN:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Skin protection:
Splash contact:
Material: butyl-rubber
Minimum layer thickness: 0,7 mm
Break through time: 10 min
-Control of environmental exposure:
Prevent product from entering drains.
HANDLING and STORAGE of FURAN:
-Conditions for safe storage, including any incompatibilities:
Store under inert gas.
Refrigerate before opening.
STABILITY and REACTIVITY of FURAN:
-Reactivity:
No data available
-Possibility of hazardous reactions:
No data available
-Conditions to avoid:
No data available
SYNONYMS:
FURAN
Divinylene oxide
Furfuran
Oxole
1,4-Epoxy-1,3-butadiene
5-Oxacyclo-1,3-pentadiene
5-Oxacyclopenta-1,3-diene
Divinylene oxide
Furfuran
Tetrole
Oxacyclopentadiene
Oxole
Furane
1,4-Epoxy-1,3-butadiene
RCRA waste number U124
Furfurane
NCI-C56202
UNII-UC0XV6A8N9
UC0XV6A8N9
CHEBI:35559
Axole
HSDB 89
CCRIS 3159
EINECS 203-727-3
UN2389
RCRA waste no. U124
BRN 0103221
beta-furan
Oxol
AI3-24244
furan-
2-Furan
Furan, 98%
DSSTox_CID_646
Furan (98%)
Furan, analytical standard
EC 203-727-3
Furan, >=99%
DSSTox_RID_75708
DSSTox_GSID_20646
Furan (stabilized with BHT)
5-17-01-00291 (Beilstein Handbook Reference)
CHEMBL278980
DTXSID6020646
Furan 1000 microg/mL in Methanol
ZINC2041074
Tox21_200920
MFCD00003222
Furan 100 microg/mL in Acetonitrile
AKOS000120038
MCULE-6076190179
UN 2389
Furan [UN2389]
NCGC00091774-01
NCGC00091774-02
NCGC00258474-01
CAS-110-00-9
F0074
FT-0626569
FT-0659712
A802126
Q243992
J-002361
BRD-K65278478-001-01-0
F0001-0213
