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Home > Encyclopedia > 2-(Bromomethyl)oxirane

2-(Bromomethyl)oxirane

2-(Bromomethyl)oxirane structure

2-(Bromomethyl)oxirane 

structure
  • CAS No:

    3132-64-7

  • Formula:

    C3H5BrO

  • Chemical Name:

    2-(Bromomethyl)oxirane

  • Synonyms:

    Oxirane,2-(bromomethyl)-;Epibromohydrin;Propane,1-bromo-2,3-epoxy-;Oxirane,(bromomethyl)-;2-(Bromomethyl)oxirane;(Bromomethyl)ethylene oxide;1-Bromo-2,3-epoxypropane;Epibromhydrin;1,2-Epoxy-3-bromopropane;Bromohydrin;3-Bromo-1,2-epoxypropane;2,3-Epoxypropyl bromide;(Bromomethyl)oxirane;(±)-3-Bromo-1,2-epoxypropane;(±)-(Bromomethyl)oxirane;(±)-Epibromohydrin;NSC 630;Oxiranylmethyl bromide;Epoxy bromopropane;Glycidyl bromide;82584-73-4

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

colourless liquid


Epibromohydrin appears as a colorless volatile liquid. Flash point 22°F. Slightly soluble in water and denser than water. Toxic by inhalation and ingestion. A strong skin irritant. Used to make rubber.


Epibromohydrin appears as a colorless volatile liquid. Flash point 22°F. Slightly soluble in water and denser than water. Toxic by inhalation and ingestion. A strong skin irritant. Used to make rubber.|Epibromohydrin is an epoxide that is oxirane substituted by a bromomethyl group at position 2. It has a role as a mutagen. It is an epoxide and an organobromine compound. It derives from a 1,2-epoxypropane.

2-(Bromomethyl)oxirane Basic Attributes

136.98

136.98

221-525-3

630

2558

DTXSID5025237

Liquid

2910900090

Characteristics

12.5

0.85

Epibromohydrin appears as a colorless volatile liquid. Flash point 22°F. Slightly soluble in water and denser than water. Toxic by inhalation and ingestion. A strong skin irritant. Used to make rubber.

1.601 g/cm3

-40 °C

134.6 °C

133 °F

1.504

In water, 3.9X10+4 mg/L (est)

2-8°C

9.9 mm Hg at 25 deg C (est)

Abdominal cavity-rat LD50: 300 mg/kg

Inflammable in case of open flame, high temperature, strong oxidant; decomposes toxic hydrogen bromide gas upon heating

Henry's Law constant = 2.4X10-6 atm-cu m/mole (est)

Hydroxyl radical reaction rate constant = 4.8X10-13 cu cm/molecule-sec at 25 °C (est)

Highly flammable. Slightly soluble in water. Sensitive to prolonged exposure to light and moisture.

Halogenated Organic Compounds

Highly Flammable

EPIBROMOHYDRIN reacts with acids, bases, oxidizing agents, Na, Zn, Al, Mg and their alloys. (NTP, 1992).

Safety Information

I

6.1(a)

UN 2558 6.1/PG 1

2

22-36/37/38-40

26-36/37

TX4115000

Xn

Completely packed, lightly placed; storeroom ventilated, away from open flames, high temperature, and stored separately from oxidants

Stable. Incompatible with acids, bases, oxidizing agents, many of the more active metals.

P261-P281-P305 + P351 + P338

H226-H302-H315-H319-H335-H351

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.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable - 2nd degree

|Warning|H226 (95.35%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P310, P302+P352, P303+P361+P353, P312, P321, P322, P330, P361, P363, P370+P378, P403+P235, P405, and P501

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]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. SMALL SPILL: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|Personnel Protection: Keep upwind. Wear positive pressure self-contained breathing apparatus. Avoid bodily contact with the material. Wear appropriate chemical protective clothing.

A dangerous fire hazard when exposed to heat or flame.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.|Personnel Protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment.

/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for EPIBROMOHYDRIN (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Toxicity

highly toxic

Epibromohydrin's production and use as a flame retardant(1) and cross-linking agent for polymers(2) 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 70(SRC), determined from a log Kow of 0.85(2) and a regression-derived equation(3), indicates that epibromohydrin is expected to have high mobility in soil(SRC). Volatilization of epibromohydrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of epibromohydrin from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 9.9 mm Hg(SRC), determined from a fragment constant method(5). Hydrolysis is expected to be the primary degradation process for epibromohydrin in moist soil based on the measured half-life of 16 days in water at 25 °C and pH 7(6). Biodegradation data were for epibromohydrin were not available(SRC, 2009). Analogous epichlorohydrin achieved 14% of the theoretical BOD in sewage sludge following acclimation(7), suggesting biodegradation may be an important fate process for epibromohydrin in acclimated water(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 70(SRC), determined from a log Kow of 0.85(2) and a regression-derived equation(3), indicates that epibromohydrin is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.4X10-6 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 38 hours and 22 days, respectively(SRC). Hydrolysis is expected to be the primary degradation process for epibromohydrin in water based on the measured half-life of 16 days in water at 25 °C and pH 7(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data were for epibromohydrin were not available(SRC, 2009). Analogous epichlorohydrin achieved 14% of the theoretical BOD in sewage sludge following acclimation(8), suggesting biodegradation may be an important fate process for epibromohydrin in acclimated water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), epibromohydrin, which has an estimated vapor pressure of 9.9 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase epibromohydrin 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 34 days(SRC), calculated from its rate constant of 4.8X10-13 cu cm/molecule-sec at 25 °C(3), determined using a structure estimation method(3). Direct photolysis of epibromohydrin is not an important environmental fate process(4).

The rate constant for the vapor-phase reaction of epibromohydrin with photochemically-produced hydroxyl radicals has been estimated as 4.8X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 34 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The first-order neutral hydrolysis rate constant has been experimentally determined to be 5X10-7 sec-1 at pH 7 and 25 °C, which corresponds to a half-life of 16 days in water(2). Hydrolysis of epibromohydrin yields 1-bromo-2,3-propanediol. Anions such as chloride will also react with epibromohydrin to yield 1-bromo-3-chloro-2-propanol(3). Bicarbonate or nitrate anions will react to yield transient intermediates, which are rapidly degraded to 1-bromo-2,3-propanediol(3). Direct photolysis of epibromohydrin is not an important environmental fate process(3).

An estimated BCF of 3 was calculated for epibromohydrin(SRC), using a log Kow of 0.85(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.

The Koc of epibromohydrin is estimated as 70(SRC), using a log Kow of 0.85(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that epibromohydrin is expected to have high mobility in soil(SRC).

The Henry's Law constant for epibromohydrin is estimated as 2.4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that epibromohydrin 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 38 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 22 days(SRC). Epibromohydrin's estimated Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of epibromohydrin from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 9.9 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1821 workers (272 of these were female) were potentially exposed to epibromohydrin in the US(1). Occupational exposure to epibromohydrin may occur through inhalation and dermal contact with this compound at workplaces where epibromohydrin is produced or used(SRC). Use data indicate that the general population may be exposed to epibromohydrin via dermal contact with products containing this compound(SRC).

Drug Information

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

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. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. 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. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

Immediate first aid: Remove patient from contact with the material. Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Dichloropropane, dichloropropene, and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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 dry sterile dressings after decontamination ... . /Dichloropropane, dichloropropene, and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dichloropropane, dichloropropene, and related compounds/

2-(Bromomethyl)oxirane Use and Manufacturing

Methods of Manufacturing

Mix 1000ml of 1, 3-dibromo-2-propanol with 1500ml of water, add 400g of calcium hydroxide (88%) in portions, and stir while adding. Then add 400g of calcium hydroxide again, and distill out the epoxy bromopropane under reduced pressure. The distillate is dried over anhydrous sodium sulfate, distilled, and collected at 134-136℃ to obtain the finished product, which is 1130-1200g, yield 84-89% .

Uses

Bromohydrin pyrophosphate enhances antibody-dependent cell-mediated cytotoxicity induced by therapeutic antibodies.

Oxirane, 2-(bromomethyl)-: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.|Not registered

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:136.98
XLogP3:0.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:135.95238
Monoisotopic Mass:135.95238
Topological Polar Surface Area:12.5
Heavy Atom Count:5
Complexity:37.9
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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