Bromoacetic acid methyl ester
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Bromoacetic acid methyl ester
structure -
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CAS No:
96-32-2
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Formula:
C3H5BrO2
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Chemical Name:
Bromoacetic acid methyl ester
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Synonyms:
Acetic acid,2-bromo-,methyl ester;Acetic acid,bromo-,methyl ester;Methyl bromoacetate;Bromoacetic acid methyl ester;Methyl α-bromoacetate;Methyl monobromoacetate;Methyl 2-bromoacetate;Carbomethoxymethyl bromide;2-Bromoacetic acid methyl ester;NSC 2642;Methyl 2-bromoethanoate
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CAS No:
Description
Colorless liquid
Methyl bromoacetate appears as a colorless to straw-colored liquid with a sharp penetrating odor. Denser than water and soluble in water. Severly irritates skin and eyes. Toxic by ingestion and inhalation. Used to make vitamins and pharmaceuticals.
Methyl bromoacetate appears as a colorless to straw-colored liquid with a sharp penetrating odor. Denser than water and soluble in water. Severly irritates skin and eyes. Toxic by ingestion and inhalation. Used to make vitamins and pharmaceuticals.
Bromoacetic acid methyl ester Basic Attributes
152.97
152.97
506256
202-499-2
LI6481MCM6
2642
2643
DTXSID7052737
Colorless to straw-colored liquid
29159080
Characteristics
26.3
0.84
Clear colorless to slightly yellow Liquid
1.6±0.1 g/cm3
205-207 °C @ Solvent: Water
132 °C
145 °F
1.450
Miscible with methanol, ether and acetone. Slightly miscible with water
Store at R.T.
18 hPa (50 °C)
Intravenous-Mouse LDL0: 15.8 mg/kg
Open flame is flammable; high heat emits toxic bromide gas
Sharp penetrating odor
Henry's Law constant = 3.54X10-5 atm-cu m/mol at 25 °C (est)
Lachrymator|Hydroxyl radical reaction rate constant = 2.17X10-13 cu cm/molecule-sec at 25 °C (est)
Highly flammable. Soluble in water.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Highly Flammable
METHYL BROMOACETATE is a halogenated ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Corrosive
Safety Information
II
6.1
UN 2643 6.1/PG 2
3
25-34-37-23/24/25-40-36/37/38-38
26-36/37/39-45-28A-36-16
AF6300000
T,Xi,F
The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives
Stable under recommended storage conditions.
P261-P280-P301 + P310-P305 + P351 + P338-P310
H301-H314-H335
SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product
Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. (ERG, 2016)|Flammable - 2nd degree
|Danger|H301 (98.21%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 56 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. 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 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: 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 damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2016)
Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: 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)|Eye/face protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers.
ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations (see section 13). Keep in suitable, closed containers for disposal.
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.|ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.|Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.
/GUIDE 155 SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.|/GUIDE 155 SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 155 SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ 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 in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind, uphill and/or upstream. Ventilate enclosed areas.|/GUIDE 155 SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ 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 Methyl bromoacetate (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. Methyl bromoacetate included on the dangerous goods list.|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. Methyl bromoacetate is included on the dangerous goods list.
Severly irritates skin and eyes.
Occupational exposure to methyl bromoacetate may occur through inhalation and dermal contact with this compound at workplaces where methyl bromoacetate is produced or used. The general population is not likely to be exposed to methyl bromoacetate. (SRC)
Toxicity
highly toxic
IDENTIFICATION AND USE: Methyl bromoacetate is a colorless to straw-colored liquid. It is used as a chemical intermediate. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Fifty chemicals were experimentally screened for toxicity. Mice and rabbits were used in the tests. Chemicals were given iv, dermally, in the eye, or ip. Methyl bromoacetate was one of the most toxic of these chemicals.
LD50 Rat oral 50 - 300 mg/kg bw
Methyl bromoacetate's production and use as a chemical intermediate for weed killers, dyes, vitamins and drugs(1) may result in its release to the environment through various waste streams(SRC). Its use as a lachrymator(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl bromoacetate is expected to have very high mobility in soil(SRC). Volatilization of methyl bromoacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Methyl bromoacetate is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.1 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2018).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl bromoacetate is not 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 3.5X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.4 and 14 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of 0.72(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis may be an important environmental fate based on base-catalyzed half-lives of 7 days and 17 hours at pH 7 and 8, respectively(2). Biodegradation data in water were not available(SRC, 2018).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl bromoacetate, which has an estimated vapor pressure of 6.1 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl bromoacetate 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 74 days(SRC), calculated from its rate constant of 2.2X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Methyl bromoacetate does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of methyl bromoacetate with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 74 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 11 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 7 days and 17 hours at pH values of 7 and 8, respectively(1). Methyl bromoacetate does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for methyl bromoacetate(SRC), using an estimated log Kow of 0.72(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of methyl bromoacetate can be estimated to be 6(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl bromoacetate is expected to have very high mobility in soil(SRC).
The Henry's Law constant for methyl bromoacetate is estimated as 3.5X10-5 atm-cu m/mole(SRC) developed using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl bromoacetate 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 1.4 days(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 14 days(SRC). Methyl bromoacetate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Methyl bromoacetate is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.1 mm Hg(SRC), determined from a fragment constant method(1).
Drug Information
Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
/SRP:/ Immediate fist aid: 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. /Esters and Related compounds/|/SRP:/ 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 ... . Monitor for shock 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 ... . /Esters and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. 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. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/
Bromoacetic acid methyl ester Use and Manufacturing
It is obtained by brominating acetic acid and then performing esterification reaction with methanol. Add glacial acetic acid, acetic anhydride, red phosphorus and a few pieces of zeolite to the drying reactor, heat to reflux, when the temperature rises to 60-70 ℃, start slowly adding bromine, and keep warm for about 1h after the addition. Cooling and filtering, and then distillation under reduced pressure to obtain bromoacetic acid. Add bromoacetic acid and methanol to carbon tetrachloride, then add sulfuric acid, heat to reflux for dehydration. After the dehydration is complete, distill the carbon tetrachloride, and then add methanol to reflux for 1h to recover methanol, and the residue is washed, dried and decompressed After distillation, you get the finished product.
Methyl bromoacetate was used in the synthesis of novel coumarins. It was also employed in the synthesis of cis-cyclopropanes
Acetic acid, 2-bromo-, methyl ester: ACTIVE
Fire Hazards -> Flammable - 2nd degree
Computed Properties
Molecular Weight:152.97
XLogP3:0.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:151.94729
Monoisotopic Mass:151.94729
Topological Polar Surface Area:26.3
Heavy Atom Count:6
Complexity:52.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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