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Benzofuran

Benzofuran structure

Benzofuran 

structure
  • CAS No:

    271-89-6

  • Formula:

    C8H6O

  • Chemical Name:

    Benzofuran

  • Synonyms:

    Benzofuran;2,3-Benzofuran;Coumarone;1-Oxindene;Benzofurfuran;Benzo[b]furan;R 7204;AT 33852;NSC 1255;1-Benzofuran

  • Categories:

    Analytical Chemistry  >  Standard

Description

2,3-Benzofuran is a colorless, sweet-smelling, oily liquid made by processing coal into coal oil. It may also be formed during other uses of coal or oil. 2,3-Benzofuran is not used for any commercial purposes, but the part of the coal oil that contains 2,3-benzofuran is made into a plastic called coumarone-indene resin. This resin resists corrosion and is used to make paints and varnishes. The resin also provides water resistance and is used in coatings on paper products and fabrics. It is


2,3-benzofuran is a clear oily yellow liquid with an aromatic odor. (NTP, 1992)|Liquid|COLOURLESS OILY LIQUID WITH CHARACTERISTIC ODOUR.


2,3-benzofuran is a clear oily yellow liquid with an aromatic odor. (NTP, 1992)|2,3-Benzofuran is a colorless, sweet-smelling, oily liquid made by processing coal into coal oil. It may also be formed during other uses of coal or oil. 2,3-Benzofuran is not used for any commercial purposes, but the part of the coal oil that contains 2,3-benzofuran is made into a plastic called coumarone-indene resin. This resin resists corrosion and is used to make paints and varnishes. The resin also provides water resistance and is used in coatings on paper products and fabrics. It is used as an adhesive in food containers and some asphalt floor tiles. The resin has been approved for use in food packages and as a coating on citrus fruits. We do not know how often the resin is used or whether any 2,3-benzofuran in the coating or packaging gets into the food.|1-benzofuran is a benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans. It is a benzofuran and a member of 1-benzofurans.

Benzofuran Basic Attributes

118.13

118.13

107704

205-982-6

LK6946W774

0388

1255

1993

DTXSID6020141

Not solid @ -18 °C; oil|Colorless, oily liquid

29329900

Characteristics

13.1

2.67

Yellow to green to yellow-brown Crystalline Powder or Crystals

1.0913 g/cm3 @ Temp: 25 °C

<-18 °C

174 °C @ Press: 760 Torr

133 °F

1.600

H2O: insoluble

2-8°C

Vapour pressure, kPa at 25°C: 0.06

Abdominal cavity-mouse LD50: 500 mg/kg

Open flame, heat, oxidants are combustible; burning emits irritating smoke

Above 56 deg C explosive vapor/air mixtures may be formed.

Aromatic odor

3.73e-11 cm3/molecule*sec

Volatile with steam|Polymerizes slowly to polybenzofuran at ambient temperatures, more rapidly with heat and in the presence of acidic catalyst. Resistant to aqueous alkali.|Hydroxyl radical reaction rate constant = 3.73X10-11 cu cm/molecule-sec @ 25 °C

Highly flammable. May be sensitive to prolonged exposure to air. Very slightly water soluble.

Ethers

Highly Flammable

2,3-BENZOFURAN slowly polymerizes on standing. It may be sensitive to prolonged exposure to air. This compound is polymerized by H2SO4. (NTP, 1992)

Safety Information

III

3

UN 1993 3/PG 3

3

40-52-10

36/37-16

DF6423800

Xn,Xi

The warehouse is ventilated, low temperature and dry; lightly loaded and unloaded, stored separately from oxidants and acids

Irritant

P273-P281

H226-H351-H412

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for BENZOFURAN (6 total), please visit the HSDB record page.

This compound is polymerized by H2SO4.

DHHS/ATSDR; Toxicological Profile for Benzofuran TP-91/04 (1992)|DHHS/NTP; Toxicology & Carcinogenesis Studies of Benzofuran in F344/N Rats and B6C3F1 Mice Technical Report Series No. 370 (1989) NIH Publication No. 90-2825

This chemical is combustible. (NTP, 1992)|Flammable. Above 56 °C explosive vapour/air mixtures may be formed.

|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P280, P281, P303+P361+P353, P308+P313, P314, P370+P378, P403+P235, P405, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

Flammable; flash point: 56 °C

Above 56 °C explosive vapor/air mixtures may be formed.

/Use/ foam, dry powder, carbon dioxide. ...Keep drums, etc., cool by spraying with water.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for BENZOFURAN (9 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Remove all ignition sources. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in covered containers as far as possible.

Fireproof. Well closed. Cool.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance may have effects on the kidneys and liver. This substance is possibly carcinogenic to humans.

NO open flames, NO sparks and NO smoking. Above 56 °C use a closed system, ventilation and explosion-proof electrical equipment.

AVOID ALL CONTACT!

2,3-Benzofuran is a colorless, sweet-smelling, oily liquid made by processing coal into coal oil. It may also be formed during other uses of coal or oil. 2,3-Benzofuran is not used for any commercial purposes, but the part of the coal oil that contains 2,3-benzofuran is made into a plastic called coumarone-indene resin. This resin resists corrosion and is used to make paints and varnishes. The resin also provides water resistance and is used in coatings on paper products and fabrics. It is used as an adhesive in food containers and some asphalt floor tiles. The resin has been approved for use in food packages and as a coating on citrus fruits. We do not know how often the resin is used or whether any 2,3-benzofuran in the coating or packaging gets into the food.

Benzofuran has been detected in exhaust gases from both gasoline and diesel engines(1-3). The amount of benzofuran detected in exhaust gases from the combustion of various hydrocarbon fuels ranged from <0.1 to 2.8 ppm(2). Emissions of benzofuran from a diesel-powdered medium duty truck was 53.2 ug benzofuran per km(3). Benzofuran has been detected in the exhaust of a four-stroke outboard motor(4). Benzofuran was qualitatively detected in water effluents collected from an advanced treatment facility in Pomona, CA on Sep 25, 1974(5). Aqueous condensate from a coal gasification facility in Morgantown, WV contained a benzofuran conc of 267 ppb(6).

RURAL/REMOTE: Benzofuran was qualitatively detected in vapor-phase ambient air samples collected in the Kanawha Valley, WV in Sept 1977(1).

Thermal decomposition of food wrapping materials made from polyvinylidene chloride yielded 60.6 to 75.2 ug benzofuran/g polymer(1). Benzofurans are emitted by heating coated (painted) steel plates to 350 °C(2).

Toxicity

moderately toxic

LD50 Mouse ip 500 mg/kg

... Toxicology and carcinogenesis studies were conducted by admin benzofuran (approx 99% pure) in corn oil by gavage to groups of /50 male F344 N rats/ at 30 or 60 mg/kg and 60 or 120 mg/kg /to groups of 50 female F344 N rats for 2 yr/. /Groups of 50 male B6C3F1 mice were dosed/ with 60 or 120 mg/kg and /groups of 50 female B6C3F1 mice were dosed with 120 or 240 mg/kg for 2 yr. ... Under the conditions of these two yr gavage studies, there was no evidence of carcinogenic activity of benzofuran for male F344/N rats receiving doses of 30 or 60 mg/kg/day. There was some evidence of carcinogenic activity of benzofuran for female F344/N rats based on incr incidences of tubular cell adenocarcinomas of the kidney. There was clear evidence of the carcinogenic activity for male and female B6C3F1 mice, based on incr incidences of neoplasms of the liver, lung and forestomach.

No large-scale commercial use has been found for benzofuran. Benzofuran has been detected in exhaust gases from both gasoline and diesel engines(2,3). Benzofuran has been detected in emissions from waste incineration(4). Benzofuran is a component of coal-tar resins(5).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 680(SRC), determined from a log Kow of 2.67(2) and a regression-derived equation(3), indicates that benzofuran is expected to have low mobility in soil(SRC). Volatilization of benzofuran from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.3X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Benzofuran is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.44 mm Hg(4). Based upon studies in water which illustate that benzofuran biodegrades in the presence of creosote-adapted microorganisms(5,6), this compound may also biodegrade in soils if acclimation has occurred(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 680(SRC), determined from a log Kow of 2.67(2) and a regression-derived equation(3), indicates that benzofuran is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.3X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hours and 5 days, respectively(SRC). According to a classification scheme(5), a BCF of 360 for guppies(6), suggests bioconcentration in aquatic organisms is moderate(SRC). Benzofuran has been shown to biodegrade in the presence of creosote-adapted microorganisms(SRC). Benzofuran biodegraded using a enriched culture from a creosote contaminated site(7) where biodegradation of benzofuran was enhanced by the degradation of other creosote compounds(7). Benzofuran was completely removed in combination with toluene, p-xylene, m-xylene, naphthalene, 1-methylnapthalene within the first 12 days of incubation, compared with a 7% loss in the acidified control microcosm(7). After 27 days, complete removal of benzofuran was observed in combination with other primary creosote substituents except 1-methylnapthalene where 95% removal was observed(7). In a study using aerobic groundwater microcosms, benzofuran at 3.3 mg/l degraded completely after 95 days (lag period = 70 days) from an aquifer contaminated with creosote compounds while from a background aquifer, benzofuran degraded after 285 days (lag period = 278 days)(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzofuran, which has a vapor pressure of 0.44 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase benzofuran is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hours(SRC), calculated from its rate constant of 37X10-12 cu cm/molecule-sec at 25 °C(3). Vapor-phase benzofuran is also degraded in the atmosphere by reaction with ozone(4); the half-life for this reaction in air is estimated to be about 6 days(SRC). Benzofuran absorbs light in the environmental UV spectrum (absorption max = 285 nm)(5); thus it has the potential for direct photolysis(SRC).

The rate constant for the vapor-phase reaction of benzofuran with photochemically-produced hydroxyl radicals has been estimated as 37X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). The rate constant for the vapor-phase reaction of benzofuran with photochemically-produced ozone molecules has been estimated as 1.8X10-18 cu cm/molecule-sec at 25 °C(2). This corresponds to an atmospheric half-life of about 6 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(SRC). Benzofuran is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Benzofuran absorbs light in the environmental UV spectrum (absorption max = 285 nm)(4); thus it has the potential for direct photolysis(SRC). Benzofuran slowly polymerizes upon standing(5).

The BCF of benzofuran in guppies exposed to 100-250 ul of a hetero PAH in 3 liters of 1:1 tapwater/deionized water for 48 hours was 360(1). According to a classification scheme(2), this BCF suggests bioconcentration in aquatic organisms is moderate(SRC).

The Koc of benzofuran is estimated as 680(SRC), using a log Kow of 2.67(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that benzofuran is expected to have low mobility in soil(SRC). Sorption of creosote compounds (including benzofuran) were measured on natural clayey till soil column(4). A Kd of 1.4 l/kg was measured for benzofuran (in presence of other creosote compounds) with a time for 50% breakthrough on the column nearly equivalent to non-adsorbing bromide ions (e.g., 37 days)(4). This data suggests that benzofuran is weakly sorbed on clayey till soil(SRC).

The Henry's Law constant for benzofuran is estimated as 5.3X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that benzofuran is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 2 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5 days(SRC). Benzofuran is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.44 mm Hg(3).

GROUNDWATER: Benzofuran has been qualitatively detected in a contaminated aquifer located near St Louis Park, MN(1); the contamination was the result of leaching from a creosote and wood preserving facility that operated from 1918 to 1982(1). Well waters collected at two coal gasification facility sites in WY contained benzofuran levels of 0.05 to 111 ppb(2). Benzofuran was detected in groundwater at 3 creosote-contaminated sites in Denmark with concentrations ranging from not detected (detection limit = 0.05 ug/l) to 16 ug/l(3).|DRINKING WATER: Trace levels (conc not reported) of benzofuran were detected in raw and treated drinking water samples collected from 15 communities in Iowa and Nebraska(1).

Benzofuran has been identified as a component of the aroma produced by coffee roasting(1).

Benzofuran was qualitatively detected in 3 of 12 samples of human milk collected from women living in Bayonne, NJ, Jersey City, NJ, Bridgeville, PA, and Baton Rouge, LA(1).

Occupational exposure to benzofuran may occur through inhalation and dermal contact with this compound at workplaces where benzofuran is produced or used(SRC). Monitoring data indicate that the general population may be exposed to benzofuran via inhalation of vapor and particulates containing benzofuran that are released in exhausts from combustion processes such as gasoline and diesel engines(1-3), and waste incineration(4).

Benzofuran was qualitatively detected in 3 of 12 samples of human milk collected from women living in Bayonne, NJ, Jersey City, NJ, Bridgeville, PA, and Baton Rouge, LA(1).

Drug Information

The partitioning of 2,3-benzofuran between particulate matter and synthetic alveolar surfactant in vitro was reported to depend upon the chemical nature of the particles. Synthetic lung surfactant was able to dissolve 2,3-benzofuran adsorbed to particles with few active sites, but not 2,3-benzofuran adsorbed to particles with many active sites. These data indicate that inhalation of particles containing 2,3-benzofuran would result in some absorption, depending on the nature of the particles.

The urinary excretion of metabolites of 2,3-benzofuran was studied in Sprague-Dawley rats (n = 5) given a single dose of 150 mg/kg i.p. Urine samples were collected at defined intervals up to 7 days postdose and analyzed using (1). H NMR and directly coupled high performance liquid chromatography (HPLC)-NMR, HPLC-(mass spectrometry) MS and HPLC-MS-NMR methods. The principal metabolites were determined to be 2-hydroxyphenylacetic acid and 2-(2-hydroxyethyl)phenyl hydrogen sulfate, representing 24.3 +/- 6.0% and 19.6 +/- 6.4% of the dose, respectively.|...The metabolism of several other substituted furans has been shown to involve oxidation by P-450, with the unsubstituted double bond of the furan ring converted either to an epoxide or to a dialdehyde. Pretreatment with inducers and inhibitors of P-450 modified the toxicity of a single ip injection of 2,3-benzofuran to male mice. Oral exposure to 2,3-benzofuran altered the activity of P-450 and other enzymes in the livers of female mice. These experiments indicate that cytochrome P-450 may be involved in the toxicity of 2,3-benzofuran, but do not provide a clear picture of 2,3-benzofuran metabolism.

The liver is a common target organ for substituted furan compounds. Ten days of oral exposure of female mice to a dose of 591 mg/kg/day of 2,3-benzofuran altered the activity of several hepatic enzymes, decreasing the rate of reactions which activate electrophiles and increasing the rate of reactions which deactivate electrophiles.

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid and irritating smoke and fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/HUMAN EXPOSURE STUDIES/ No skin lesions or dermatitis were reported in an early review of the dermatological problems associated with the manufacture of coumarone-indene resin (a polymer made from 2,3-benzofuran and indene); however, the manufacturing process essentially prevented contact with monomers, so the significance of these negative findings is questionable. Workers continuously exposed to wood varnished with coumaroneindene resin developed dermatitis, but the sensitivity was attributed to the sulfuric acids in the varnish.

2,3-benzofuran

The substance can be absorbed into the body by inhalation of its aerosol.

See Effects of long-term or repeated exposure.

Gastrointestinal (Stomach and Intestines, part of the digestive system), Hepatic (Liver), Renal (Urinary System or Kidneys), Respiratory (From the Nose to the Lungs)

Benzofuran Use and Manufacturing

Methods of Manufacturing

O-formylphenoxyacetic acid is prepared by the reaction of salicylaldehyde and monochloroacetic acid, which is obtained by ring closure. The coumarin is heated to 860°C to produce gaseous products and viscous material, and the viscous material is fractionated, of which 172-174°C is divided into benzofuran. Benzofuran can also be separated from coal tar. The heavy benzene and light oil fractions are mixed, and the 160-215 fraction is cut by distillation, which contains about 4% of benzofuran. However, this fraction is usually used to produce indene-gumarone resin without the need to propose pure products.

Uses

manufacture of coumarone-indene resins.

Benzofuran: ACTIVE

The analyte can be extracted from water and gas chromatographed as determined by Athen-ERH or S-Cubed.|Method: High Resolution Gas Chromatography/Mass Spectrometry; Analyte: 2,3-benzofuran; Matrix: forest air; Detection Level: not provided. /From table/|Method: High Resolution Gas Chromatography/Mass Spectrometry; Analyte: 2,3-benzofuran; Matrix: automobile exhaust; Detection Level: 0.1 ppm. /From table/|Method: High Resolution Gas Chromatography/Mass Spectrometry; Analyte: 2,3-benzofuran; Matrix: groundwater and process water; Detection Level: 0.1 ppb. /From table/|Method: Gas Chromatography/Mass Spectrometry; Analyte: 2,3-benzofuran; Matrix: whey powder; Detection Level: not provided. /From table/

Method: High Resolution Gas Chromatography/Mass Spectrometry; Analyte: 2,3-benzofuran; Matrix: blood; Detection Level: not provided. /From table/|Method: Gas Chromatography/Mass Spectrometry; Analyte: 2,3-benzofuran; Matrix: breast milk; Detection Level: not provided. /From table/

Computed Properties

Molecular Weight:118.13
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Exact Mass:118.041864811
Monoisotopic Mass:118.041864811
Topological Polar Surface Area:13.1
Heavy Atom Count:9
Complexity:101
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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