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Product No: AR0309

Furan, (Stabilized with 0.025 to 0.04 % W/V BHT)

Name: Furan
Brand: Chempure
Rating: 4 (1 reviews)

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CAS Number

110-00-9

Molecular Weight

68.07

Formula

C4H4O

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About this item

IUPAC name	furan
canonical smiles	C1=COC=C1
inchi	InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
inchi key	YLQBMQCUIZJEEH-UHFFFAOYSA-N
molecular formula	C4H4O
synonyms	FURAN 110-00-9 Divinylene oxide Furfuran Tetrole
Compound Description	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. It is a toxic, flammable, low-boiling colourless liquid. It has a role as a carcinogenic agent, a hepatotoxic agent and a Maillard reaction product. It is a mancude organic heteromonocyclic parent, a member of furans and a monocyclic heteroarene. Furan is a natural product found in Perilla frutescens, Solanum lycopersicum, and Coffea arabica with data available. Furan is a clear, colorless, flammable liquid cyclic ether with an ethereal odor. Furan is used as an intermediate in the production of tetrahydrofuran, pyrrole and thiophene. Inhalation exposure to this substance causes eye and skin irritation and central nervous system depression. Furan is mutagenic in animals and is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether and acetone, but is insoluble in water. It is toxic and may be carcinogenic. Furan is used as a starting point to other specialty chemicals. 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 are also referred to as furans. 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. 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 in the Paal-Knorr Synthesis. The thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products. 2,4-Disubstituted furans can be synthesized by sulfone-mediated cyclization of 1,3-diketones

Computed Properties

Molecular Weight:	68.07 g/mol
XLogP3:	1.3
Hydrogen Bond Donor Count:	0
Hydrogen Bond Acceptor Count:	1
Rotatable Bond Count:	0
Exact Mass:	68.026214747 g/mol
Monoisotopic Mass:	68.026214747 g/mol
Topological Polar Surface Area:	13.1 Å²
Heavy Atom Count:	5
Formal Charge:	0
Complexity:	22.8
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	0
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Danger
hazard classes and categories	Flam. Liq. 1 (100%) Acute Tox. 4 (100%) Skin Irrit. 2 (100%) Acute Tox. 1 (20.83%) Acute Tox. 4 (79.17%) Muta. 2 (99.65%) Carc. 1B (99.65%) STOT RE 2 (100%) Aquatic Chronic 3 (100%) Acute toxicity - category 4 Skin irritation - category 2 Germ cell mutagenicity - category 2 Carcinogenicity - category 1B Specific target organ toxicity (repeated exposure) - category 2 Flammable liquid - category 1 Hazardous to the aquatic environment (chronic) - category 3 Flammable liquids - Category 1 Acute toxicity (Inhalation: Vapours) - Category 3 Germ cell mutagenicity - Category 2 Carcinogenicity - Category 2 Specific target organ toxicity - Single exposure - Category 2 (central nervous system, digestive system, liver), Category 3 (respiratory tract irritation) Specific target organ toxicity - Repeated exposure - Category 1 (liver, kidney, respiratory system), Category 2 (testis, ovaria) Hazardous to the aquatic environment (Acute) - Category 3 Specific target organ toxicity - Single exposure - Category 2 (central nervous system, digestive system, liver), Category 3 (respiratory tract irritation) Specific target organ toxicity - Repeated exposure - Category 1 (liver, kidney, respiratory system), Category 2 (testis, ovaria) Carcinogens, Flammable - 4th degree, Reactive - 1st degree Flam. Liq. 1 Carc. 1B Muta. 2 Acute Tox. 4 * STOT RE 2 * Skin Irrit. 2 Aquatic Chronic 3
precautionary statement codes

toxicity summary	Furan is a potent hepatotoxin and hepatocarcinogen in rodents, causing hepatocellular adenomas and carcinomas in rats and mice, and high incidences of cholangiocarcinomas in rats at doses ≥ 2 mg/kg bw. A genotoxic mode of action cannot be excluded for furan-induced tumor formation. Furan is metabolized by cytochrome P450 enzymes, predominantly CYP2E1, to its major metabolite cis-2-butene-1,4-dial , a highly reactive electrophile identified as the key mediator of furan toxicity and carcinogenicity. Furan-mediated effects on glutathione levels and cell viability can be suppressed by the CYP inhibitor 1-phenylimidazole and increased by pretreatment of rats with acetone , indicating that furan cytotoxicity depends on its metabolic activation. BDA has been shown to react with cellular nucleophiles such as GSH and amino acids and to cause cross-links between thiols and amino groups, giving rise to lactam and pyrrole derivatives. Furan reduced the percentage of DNA in the comet tail in turkey liver fetal hepatocytes. Furan was also shown to induce chromosomal aberrations and sister chromatid exchanges in Chinese hamster ovary cells. A statistically significant increase of micronucleated cells was recently reported in the spleen of furan-treated mice. A reduction of percentage of DNA in comet tail in liver cells was observed following treatment of turkey fetuses in ovo. Exposure to furan at doses associated with increased tumor incidences initially causes hepatocellular necrosis, accompanied by inflammation and sustained regenerative proliferation of hepatocytes, which may present key events in furan-induced hepatocellular carcinogenicity. Subcapsular and centrilobular necrosis accompanied by markedly increased liver enzymes is the primary response to furan treatment. The involvement of inflammatory processes in furan toxicity is also reflected by increased expression of cytokines and other inflammation-associated genes, such as IFN-γ, IL-1β, IL-6, IL-10, and components of the complement system, which may, however, also derive from lesions involving the biliary tract. Indeed, increased production of reactive oxygen species in response to furan is suggested by immunohistochemical detection of 8-oxo-dG within nuclei of hepatocytes of centrilobular areas following high-dose exposure and changes in the expression of genes responsive to oxidative stress in rats and/or mice.
symptoms	Inhalation Symptoms: Sore throat. Cough. Chest tightness. Shortness of breath. Laboured breathing. Skin Symptoms: Redness. Eye Symptoms: Redness. Pain.
carcinogen classification

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Documentation

Certificate of Analysis

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CAS #

*This document is like a lab demo—an example Certificate of Analysis (COA) that showcases what a COA looks like but may not match the latest batch in all its glory. Think of it as a chemistry experiment: close, but not quite the final reaction!

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About this item

IUPAC name	furan
canonical smiles	C1=COC=C1
inchi	InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H
inchi key	YLQBMQCUIZJEEH-UHFFFAOYSA-N
molecular formula	C4H4O
synonyms	FURAN 110-00-9 Divinylene oxide Furfuran Tetrole
Compound Description	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. It is a toxic, flammable, low-boiling colourless liquid. It has a role as a carcinogenic agent, a hepatotoxic agent and a Maillard reaction product. It is a mancude organic heteromonocyclic parent, a member of furans and a monocyclic heteroarene. Furan is a natural product found in Perilla frutescens, Solanum lycopersicum, and Coffea arabica with data available. Furan is a clear, colorless, flammable liquid cyclic ether with an ethereal odor. Furan is used as an intermediate in the production of tetrahydrofuran, pyrrole and thiophene. Inhalation exposure to this substance causes eye and skin irritation and central nervous system depression. Furan is mutagenic in animals and is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. Furan is a colorless, flammable, highly volatile liquid with a boiling point close to room temperature. It is soluble in common organic solvents, including alcohol, ether and acetone, but is insoluble in water. It is toxic and may be carcinogenic. Furan is used as a starting point to other specialty chemicals. 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 are also referred to as furans. 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. 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 in the Paal-Knorr Synthesis. The thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products. 2,4-Disubstituted furans can be synthesized by sulfone-mediated cyclization of 1,3-diketones

Computed Properties

Molecular Weight:	68.07 g/mol
XLogP3:	1.3
Hydrogen Bond Donor Count:	0
Hydrogen Bond Acceptor Count:	1
Rotatable Bond Count:	0
Exact Mass:	68.026214747 g/mol
Monoisotopic Mass:	68.026214747 g/mol
Topological Polar Surface Area:	13.1 Å²
Heavy Atom Count:	5
Formal Charge:	0
Complexity:	22.8
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	0
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Danger
hazard classes and categories	Flam. Liq. 1 (100%) Acute Tox. 4 (100%) Skin Irrit. 2 (100%) Acute Tox. 1 (20.83%) Acute Tox. 4 (79.17%) Muta. 2 (99.65%) Carc. 1B (99.65%) STOT RE 2 (100%) Aquatic Chronic 3 (100%) Acute toxicity - category 4 Skin irritation - category 2 Germ cell mutagenicity - category 2 Carcinogenicity - category 1B Specific target organ toxicity (repeated exposure) - category 2 Flammable liquid - category 1 Hazardous to the aquatic environment (chronic) - category 3 Flammable liquids - Category 1 Acute toxicity (Inhalation: Vapours) - Category 3 Germ cell mutagenicity - Category 2 Carcinogenicity - Category 2 Specific target organ toxicity - Single exposure - Category 2 (central nervous system, digestive system, liver), Category 3 (respiratory tract irritation) Specific target organ toxicity - Repeated exposure - Category 1 (liver, kidney, respiratory system), Category 2 (testis, ovaria) Hazardous to the aquatic environment (Acute) - Category 3 Specific target organ toxicity - Single exposure - Category 2 (central nervous system, digestive system, liver), Category 3 (respiratory tract irritation) Specific target organ toxicity - Repeated exposure - Category 1 (liver, kidney, respiratory system), Category 2 (testis, ovaria) Carcinogens, Flammable - 4th degree, Reactive - 1st degree Flam. Liq. 1 Carc. 1B Muta. 2 Acute Tox. 4 * STOT RE 2 * Skin Irrit. 2 Aquatic Chronic 3
precautionary statement codes

toxicity summary	Furan is a potent hepatotoxin and hepatocarcinogen in rodents, causing hepatocellular adenomas and carcinomas in rats and mice, and high incidences of cholangiocarcinomas in rats at doses ≥ 2 mg/kg bw. A genotoxic mode of action cannot be excluded for furan-induced tumor formation. Furan is metabolized by cytochrome P450 enzymes, predominantly CYP2E1, to its major metabolite cis-2-butene-1,4-dial , a highly reactive electrophile identified as the key mediator of furan toxicity and carcinogenicity. Furan-mediated effects on glutathione levels and cell viability can be suppressed by the CYP inhibitor 1-phenylimidazole and increased by pretreatment of rats with acetone , indicating that furan cytotoxicity depends on its metabolic activation. BDA has been shown to react with cellular nucleophiles such as GSH and amino acids and to cause cross-links between thiols and amino groups, giving rise to lactam and pyrrole derivatives. Furan reduced the percentage of DNA in the comet tail in turkey liver fetal hepatocytes. Furan was also shown to induce chromosomal aberrations and sister chromatid exchanges in Chinese hamster ovary cells. A statistically significant increase of micronucleated cells was recently reported in the spleen of furan-treated mice. A reduction of percentage of DNA in comet tail in liver cells was observed following treatment of turkey fetuses in ovo. Exposure to furan at doses associated with increased tumor incidences initially causes hepatocellular necrosis, accompanied by inflammation and sustained regenerative proliferation of hepatocytes, which may present key events in furan-induced hepatocellular carcinogenicity. Subcapsular and centrilobular necrosis accompanied by markedly increased liver enzymes is the primary response to furan treatment. The involvement of inflammatory processes in furan toxicity is also reflected by increased expression of cytokines and other inflammation-associated genes, such as IFN-γ, IL-1β, IL-6, IL-10, and components of the complement system, which may, however, also derive from lesions involving the biliary tract. Indeed, increased production of reactive oxygen species in response to furan is suggested by immunohistochemical detection of 8-oxo-dG within nuclei of hepatocytes of centrilobular areas following high-dose exposure and changes in the expression of genes responsive to oxidative stress in rats and/or mice.
symptoms	Inhalation Symptoms: Sore throat. Cough. Chest tightness. Shortness of breath. Laboured breathing. Skin Symptoms: Redness. Eye Symptoms: Redness. Pain.
carcinogen classification

Product No: AR0309

Furan, (Stabilized with 0.025 to 0.04 % W/V BHT)

Product No: AR0309

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

About this item

Documentation

Certificate of Analysis

Require a Sample Certificate of Analysis (COA) ?

Reviews

Product No: AR0309

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

TOXICITY

Require a Sample Certificate of Analysis (COA) ?