rel-(2R,2′R)-2,2′-Bioxirane
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rel-(2R,2′R)-2,2′-Bioxirane
structure -
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CAS No:
298-18-0
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Formula:
C4H6O2
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Chemical Name:
rel-(2R,2′R)-2,2′-Bioxirane
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Synonyms:
2,2′-Bioxirane,(2R,2′R)-rel-;Butane,1,2:3,4-diepoxy-,(±)-;Threitol,1,2:3,4-dianhydro-,DL-;2,2′-Bioxirane,(R*,R*)-(±)-;rel-(2R,2′R)-2,2′-Bioxirane;dl-1,2:3,4-Diepoxybutane;2,2′-Bioxirane,(R*,R*)-;(±)-1,2:3,4-Diepoxybutane;DL-Diepoxybutane;DL-1,2:3,4-Diepoxybutane;(±)-Diepoxybutane;Rac-1,3-Butadiene diepoxide;3483-75-8;22722-01-6;34897-03-5
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CAS No:
Description
PHYSICAL DESCRIPTION: Colorless to yellow liquid. (NTP, 1992)
D,l-1,2:3,4-diepoxybutane is a colorless to yellow liquid. (NTP, 1992)|Diepoxybutane is a colorless liquid. Used in curing polymers; crosslinking textile fibers and to prevent spoilage. (EPA, 1998)
D,l-1,2:3,4-diepoxybutane is a colorless to yellow liquid. (NTP, 1992)|Diepoxybutane is a colorless liquid. Used in curing polymers; crosslinking textile fibers and to prevent spoilage. (EPA, 1998)|Diepoxybutane is an epoxide. It has a role as a mutagen.
rel-(2R,2′R)-2,2′-Bioxirane Basic Attributes
86.089
86.09
206-060-6
629
2929|3384|3082
DTXSID0041307
Water-white
Characteristics
25.06000
-0.52
D,l-1,2:3,4-diepoxybutane is a colorless to yellow liquid. (NTP, 1992)
1.4±0.1 g/cm3
3 °C
144 °C
45.6±0.0 °C
1.546
greater than or equal to 100 mg/mL at 67.1° F (NTP, 1992)
PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/
3.9 mm Hg at 68° F (NTP, 1992)
LD50 oral in rat: 210mg/kg
MS: NIST 615 (NIST/EPA/MSDC Mass Spectral Database 1990 Version); WILEY 135 (Atlas of Mass Spectral Data, John Wiley & Sons, New York) /Butadiene dioxide (meso-form)/
Highly flammable. Water soluble. Slowly hydrolyzes in water.|Highly Flammable
Epoxides
Highly Flammable
D,L-1,2:3,4-DIEPOXYBUTANE is incompatible with acids, bases and oxidizing agents. Reacts with 4-(4'-nitrobenzyl)pyridine. Also reacts with alcohols, amines, phenols. (NTP, 1992)|Epoxides, such as DIEPOXYBUTANE, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.
Safety Information
2929
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U085, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.|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/|For more Disposal Methods (Complete) data for 1,2:3,4-DIEPOXYBUTANE (7 total), please visit the HSDB record page.
National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Diepoxybutane (1464-53-5) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s068diep.pdf]
This chemical is combustible. (NTP, 1992)|When heated to decomposition it emits acrid smoke and irritating fumes. (EPA, 1998)
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P271, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|H226 (82.61%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 46 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P262, P264, P270, P271, P280, P281, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501
Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. LARGE FIRE: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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)|Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 3384 datasheet. 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 should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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 store this chemical under refrigerated temperatures and away from mineral acids and bases. (NTP, 1992)|Do not touch spilled material. (EPA, 1998)
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)|For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)|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/
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/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|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/|For more Preventive Measures (Complete) data for 1,2:3,4-DIEPOXYBUTANE (10 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/
A severe skin and eye irritant.
The major hazards encountered in the use and handling of 1,2:3,4-diepoxybutane stem from its toxicologic properties. Exposure to this substance may occur from its use as a research chemical. Effects from exposure may include severe irritation of the eyes, skin, mucous membranes, and respiratory tract; gene mutation; pulmonary edema; and death. In addition, the International Agency for Research on Cancer (IARC) has designated this substance as a Group 2B carcinogen, meaning, "The agent is possibly carcinogenic to humans." Mechanical ventilation employing high-efficiency particulate arrestors or charcoal filters should be used to limit airborne levels of this substance. In activities and situations where over-exposure may occur, wear protective clothing and a respirator. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes and wash exposed skin thoroughly with soap and water. Contaminated clothing should be removed immediately. Smoking, eating, and drinking should be prohibited in 1,2:3,4-diepoxybutane work areas. This substance should be stored in a securely sealed, watertight container which is enclosed in a second, unbreakable, leakproof container. 1,2:3,4-Diepoxybutane is a good candidate for liquid injection, rotary kiln, and fluidized bed forms of incineration.
U085; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
U085; As stipulated in 40 CFR 261.33, when 2,2'-bioxirane, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Toxicity
LC50 Rat inhalation 90 ppm/4 hr|LD50 Mouse oral 72 mg/kg|LD50 Rat oral 78 mg/kg|LD50 Mouse ip 31 mg/kg|LD50 Rabbit skin 80 mg/kg
1,2:3,4-Diepoxybutane's production and use in curing polymers and crosslinking textile fibers(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from an measured log Kow of -0.28(2) and a regression-derived equation(3), indicates that 1,2:3,4-diepoxybutane is expected to have very high mobility in soil(SRC). Volatilization of 1,2:3,4-diepoxybutane from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-8 atm-cu m/mole(SRC), derived using a fragment constant estimation method(4). The potential for volatilization of 1,2:3,4-diepoxybutane from dry soil surfaces may exist(SRC) based upon a vapor pressure of 3.9 mm Hg(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a log Kow of -0.28(2) and a regression-derived equation(3), indicates that 1,2:3,4-diepoxybutane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.5X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 0.36(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2:3,4-diepoxybutane, which has a vapor pressure of 3.9 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 1,2:3,4-diepoxybutane 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 16.1 days(SRC), calculated from its rate constant of 9.96X10-13 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).
The rate constant for the vapor-phase reaction of 1,2:3,4-diepoxybutane with photochemically-produced hydroxyl radicals has been estimated as 9.96X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Based on experimentally determined hydrolysis rate constants of 7.5X10-3 to 5.0X10-3/hr for 1,2:3,4-diepoxybutane at 37 °C and neutral pH(2), calculated hydrolysis half-lives are 4-7 days(SRC). The hydrolysis half-life of 1,2:3,4-diepoxybutane at ambient temperatures is likely to be longer than at 37 °C, however, these values suggest that hydrolysis would be an important removal mechanism for 1,2:3,4-diepoxybutane in water and wet soil(SRC). 1,2:3,4-Diepoxybutane is not likely to undergo oxidation by reaction with alkyl peroxy radical in water(3). 1,2:3,4-Diepoxybutane is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).
An estimated BCF of 0.36 was calculated for 1,2:3,4-diepoxybutane(SRC), using a log Kow of -0.28(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
2.51 L/kg|The Koc of 1,2:3,4-diepoxybutane is estimated as 17(SRC), using a measured log Kow of -0.28(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,2:3,4-diepoxybutane is expected to have very high mobility in soil(SRC).
The Henry's Law constant for 1,2:3,4-diepoxybutane is estimated as 3.54X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,2:3,4-diepoxybutane is expected to be essentially nonvolatile from water and moist soil surfaces(2). The potential for volatilization of 1,2:3,4-diepoxybutane from dry soil surfaces may exist based upon a vapor pressure of 3.9 mm Hg(3).
Occupational exposure to 1,2:3,4-diepoxybutane may occur through inhalation and dermal contact with this compound at workplaces where 1,2:3,4-diepoxybutane is produced or used. (SRC)
Drug Information
Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other. (See all compounds classified as Cross-Linking Reagents.)|Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)|Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. (See all compounds classified as Carcinogens.)
Experiments were carried out to study the uptake, retention, routes of elimination, and identification of butadiene metabolites in rats and mice. Male Sprague-Dawley rats and male B6C3F1 mice were administered (14)C labeled butadiene by inhalation at 0.14 to 13000 microg/l air. The percentage of (14)C absorbed and retained at 6 hours after exposure was 1.5 to 17 in rats and 4 to 20 in mice. Major routes of elimination were exhalation and urine discharge, accounting for 75 to 85% of the total (14)C. About 12% of (14)C remained in the carcass 65 hours after the exposure. At the 13 microg/l dose, all (14)C was accounted for as metabolites. At the lowest butadiene concentrations (14)C in urine and exhaled air represented 40 and 20% of the total (14)C eliminated. At the highest butadiene concentration (14)C in urine decreased to 8 % of total (14)C eliminated or retained in carcass. More than 90% of (14)C in blood samples consisted of butadiene metabolites, of which 60 to 80 % was nonvolatile material. The amount of metabolites increased with the concentration of inhaled butadiene, but the increase was not proportional to the uptake. At 130 and 1800 microg/l butadiene mice had about twofold higher amount of 1,2-epoxy-3-butene than rats. The quantities of butadiene-diepoxide in rats subjected to the same exposure levels of butadiene were 0.1 and 1 nmol/ml blood after 6 hours. /Butadiene/
Experiments were carried out to study the uptake, retention, routes of elimination, and identification of butadiene metabolites in rats and mice. Male Sprague-Dawley rats and male B6C3F1 mice were administered (14)C labeled butadiene by inhalation at 0.14 to 13000 microg/l air. The percentage of (14)C absorbed and retained at 6 hours after exposure was 1.5 to 17 in rats and 4 to 20 in mice. Major routes of elimination were exhalation and urine discharge, accounting for 75 to 85% of the total (14)C. About 12% of (14)C remained in the carcass 65 hours after the exposure. At the 13 microg/l dose, all (14)C was accounted for as metabolites. At the lowest butadiene concentrations (14)C in urine and exhaled air represented 40 and 20% of the total (14)C eliminated. At the highest butadiene concentration (14)C in urine decreased to 8 % of total (14)C eliminated or retained in carcass. More than 90% of (14)C in blood samples consisted of butadiene metabolites, of which 60 to 80 % was nonvolatile material. The amount of metabolites increased with the concentration of inhaled butadiene, but the increase was not proportional to the uptake. At 130 and 1800 microg/l butadiene mice had about twofold higher amount of 1,2-epoxy-3-butene than rats. The quantities of butadiene-diepoxide in rats subjected to the same exposure levels of butadiene were 0.1 and 1 nmol/ml blood after 6 hours. /Butadiene/|Diepoxybutane (DEB) is a known human metabolite of butadiene_monoxide.
SYMPTOMS: Exposure to this compound in humans may cause swollen eyelids, irritation of the upper respiratory tract and painful eye irritation 6 hours past exposure. Systemic toxicity may be caused by skin contact. It causes pronounced nasal and eye irritation at 10 ppm but barely recognizable at 5 ppm after 5-minute exposure. It may also cause mucous membrane irritation. Other symptoms include severe pulmonary irritation and depression of the hematopoietic system. Other symptoms include lacrimation, clouding of the cornea, labored breathing, lung congestion, atrophy of the thymus, involution of the spleen and decreased weight gain. Causes of death are pulmonary edema and shock following extreme local irritation. It may also cause reduced or loss of spermatogenesis, leukopenia and lymphopenia. ACUTE/CHRONIC HAZARDS: This compound is highly toxic on inhalation and moderately toxic following skin absorption or ingestion. It is readily absorbed through the skin and respiratory tract. It is irritating to the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)|Severe skin and eye irritant. Accidental minor exposure caused swelling of the eyelids, upper respiratory tract irritation and painful eye irritation 6 hours after exposure.NOTE: The dl- and meso-forms (CAS Registry Numbers 298-18-0 and 564-00-1, respectively) as well as the L(-) form (CAS Registry Number 30031-64-2) have all been determined to be positive animal carcinogens. (EPA, 1998)|Carcinogens
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: 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. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. 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)|Warning: Effects may be delayed. Caution is advised. Signs and Symptoms of Diepoxybutane Exposure: Acute exposure to diepoxybutane may produce severe irritation to skin, eyes, and gastrointestinal tract. Swelling of the eyelids may be noted. Respiratory signs may include irritation of the upper respiratory tract, which may progress to pulmonary edema. Emergency Life-Support Procedures: Acute exposure to diepoxybutane may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to diepoxybutane. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to diepoxybutane. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove and isolate contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. DO NOT induce vomiting or attempt to neutralize! 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Give the victims water or milk: children up to 1 year old, 125 mL (4 oz or 1/2 cup); children 1 to 12 years old, 200 mL (6 oz or 3/4 cup); adults, 250 mL (8 oz or 1 cup). Water or milk should be given only if victims are conscious and alert. 6. Transport to a health care facility. (EPA, 1998)
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema 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. Administer activated charcoal ... . Cover skin burns with sterile dressings after decontamination ... . /Ethylene oxide and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if 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. Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene oxide and related compounds/
Fanconi anemia is characterized clinically by a progressive pancytopenia, diverse congenital abnormalities & incr predisposition to malignancy. ... Data from diepoxybutane induced chromosomal breakage studies of 328 peripheral blood specimens from patients considered at risk for Fanconi anemia were analyzed using a stepwise multivariate logistic regression. ... /Results indicate/ hypersensitivity to the clastogenic effect of diepoxybutane is a useful discriminator for Fanconi anemia. A simplified scoring method for classifying patients on the basis of 8 clinical manifestations that are the best predictors for Fanconi anemia is presented.|Poison by ingestion, inhalation, skin contact, and intraperitoneal routes.
1,2,3,4-diepoxybutane
rel-(2R,2′R)-2,2′-Bioxirane Use and Manufacturing
NOT PRODUCED COMMERCIALLY IN USA.|Prepared from erythrityl chlorohydrin; by refluxing 1,4-dichloro-2,3-butanediol in tetrahydrofuran with sodium hydroxide.|Prepared by chlorination of butadiene followed by epoxidation with peracetic acid, with subsequent hydrolysis of the epoxide group and final reepoxidation with caustic.
RESEARCH CHEMICAL|Curing polymers; crosslinking textile fibers|Chemical intermediate and in the preparation of erythritol and pharmaceuticals.
(1978) NOT PRODUCED COMMERCIALLY IN USA|(1982) NOT PRODUCED COMMERCIALLY IN USA
2,2'-Bioxirane: ACTIVE
The personal monitoring method employs the trapping reagent p-nitrobenzyl pyridine absorbed on a cellulose thin layer chromatography strip. Positive results reported for monitoring exposure to 1,2:3,4-diepoxybutane.|Gas-liquid chromatography has been suggested for determination of 1,2:3,4-diepoxybutane in air samples.
Health Hazards -> Carcinogens
Computed Properties
Molecular Weight:86.09
XLogP3:-0.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:86.036779430
Monoisotopic Mass:86.036779430
Topological Polar Surface Area:25.1
Heavy Atom Count:6
Complexity:61.9
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes