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Ethyl bromoacetate

Ethyl bromoacetate structure

Ethyl bromoacetate 

structure
  • CAS No:

    105-36-2

  • Formula:

    C4H7BrO2

  • Chemical Name:

    Ethyl bromoacetate

  • Synonyms:

    Acetic acid,2-bromo-,ethyl ester;Acetic acid,bromo-,ethyl ester;Antol;Ethyl bromoacetate;Ethyl monobromoacetate;Ethyl α-bromoacetate;Bromoacetic acid ethyl ester;Ethyl bromacetate;(Ethoxycarbonyl)methyl bromide;Ethyl 2-bromoacetate;Ethyl bromoethanoate;α-Bromoacetic acid ethyl ester;Ethyl 2-bromoethanoate;NSC 8832;2-Bromoacetic acid ethyl ester;679806-14-5;2374896-00-9

  • Categories:

    Active Pharmaceutical Ingredients  >  Other Chemical Drugs

Description

ETHYL BROMOACETATE is a clear, colorless liquid. A lachrymator. Toxic by ingestion, inhalation and skin absorption; a strong irritant of the skin. Insoluble in water and soluble in alcohol, benzene, and ether.


Ethyl 2-bromoacetate is the chemical compound with the formula CH2BrCO2C2H5. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alkylating agent and may be fatal if inhaled.


Ethyl bromoacetate appears as a clear, colorless liquid. A lachrymator. Toxic by ingestion, inhalation and skin absorption; a strong irritant of the skin. Insoluble in water and soluble in alcohol, benzene, and ether.


Ethyl bromoacetate appears as a clear, colorless liquid. A lachrymator. Toxic by ingestion, inhalation and skin absorption; a strong irritant of the skin. Insoluble in water and soluble in alcohol, benzene, and ether.

Ethyl bromoacetate Basic Attributes

167.001

167.00

203-290-9

D20KFB313W

8832

1603

DTXSID4020587

Clear colorless liquid

29159080

Characteristics

26.30000

1.37

Ethyl bromoacetate appears as a clear, colorless liquid. A lachrymator. Toxic by ingestion, inhalation and skin absorption; a strong irritant of the skin. Insoluble in water and soluble in alcohol, benzene, and ether.

1.5032 g/cm3 @ Temp: 20 °C

162 °C

168.5 °C

47.8±0.0 °C

1.453

Miscible in oxygenated and aromatic solvents

Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.

2.6 mm Hg ( 25 °C)

5.8 (Air= 1)

Pungent odor

Partially decomposed by water

Flammable. Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

ETHYL 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.

Safety Information

II

6.1

UN 1603 6.1/PG 2

1

R26/27/28

S26-S45-S7/9-S1/2

AF6000000

T+:Verytoxic;

Stable. Combustible. Incompatible with strong oxidizing agents, water, strong acids.

Missing Phrase - N15.00950417-P210-P280-P302 + P352 + P310-P304 + P340 + P310-P370 + P378

H226-H300 + H310 + H330

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Will react with water or steam to produce toxic and corrosive fumes. ... On contact with acid or acid fumes, it emits highly toxic fumes of /hydrogen bromide/.

TOXICOLOGICAL ASPECTS OF IRRITATING AGENTS ETHYLBROMOACETATE. A REVIEW.[HOLMBERG B; BIOLOGICAL ASPECTS OF CHEMICAL & BIOLOGICAL WEAPONS; AMBIO 4(5-6) 211 (1975)]

UN 1603

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, Reactive - 1st degree

|Danger|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|H226 (82.46%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P303+P361+P353, P304+P340, P310, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 58 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P305+P351+P338, P310, P370+P378, P403+P235, 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)

Flammable liquid when exposed to heat, flame, and oxidizers.

To fight fire, use water as a fire blanket.

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.

/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. Keep out of low areas. 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 ETHYL 2-BROMOACETATE (8 total), please visit the HSDB record page.

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.

An irritant to skin, eyes, and mucous membranes.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

Ethyl 2-bromoacetate's production and use as a chemical intermediate and reactant in the synthesis of an analgesic(1) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 1.12(2) and a regression-derived equation(3), indicates that ethyl 2-bromoacetate is expected to have very high mobility in soil(SRC). Volatilization of ethyl 2-bromoacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.70X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of ethyl 2-bromoacetate from dry soil surfaces may exist based upon an estimated vapor pressure of 3.37 mm Hg(5). A base-catalyzed second-order hydrolysis rate constant of 11 L/mole-sec(SRC) was estimated using a structure estimation method(6); this corresponds to half-lives of 8 days and 18 hours at pH values of 7 and 8, respectively(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of 1.12(2) and a regression-derived equation(3), indicates that ethyl 2-bromoacetate 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 2.70X10-5 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 17 hr and 12 days, respectively(SRC). A base-catalyzed second-order hydrolysis rate constant of 11 L/mole-sec(SRC) was estimated using a structure estimation method(7); this corresponds to half-lives of 8 days and 18 hours at pH values of 7 and 8, respectively(7). According to a classification scheme(5), an estimated BCF of 1(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl 2-bromoacetate, which has an estimated vapor pressure of 3.37 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl 2-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 14 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of ethyl 2-bromoacetate with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 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(2); this corresponds to half-lives of 8 days and 18 hours at pH values of 7 and 8, respectively(2).

An estimated BCF of 1 was calculated for ethyl 2-bromoacetate(SRC), using a log Kow of 1.12(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 ethyl 2-bromoacetate is estimated as 12(SRC), using a log Kow of 1.12(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ethyl 2-bromoacetate is expected to have very high mobility in soil.

The Henry's Law constant for ethyl 2-bromoacetate is estimated as 2.70X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethyl 2-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 17 hr(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 12 days(SRC). Ethyl 2-bromoacetate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of ethyl 2-bromoacetate from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 3.37 mm Hg(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 851 workers (187 of these are female) are potentially exposed to ethyl 2-bromoacetate in the US(1). Occupational exposure to ethyl 2-bromoacetate may occur through inhalation and dermal contact with this compound at workplaces where ethyl 2-bromoacetate is produced or used(SRC).

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)

VAPORS ARE IRRITANT TO ALL MUCOUS MEMBRANES, ESP TO EYES, & ARE UNBEARABLE FOR MORE THAN A MIN AT CONCN OF 8 PPM IN AIR. EXPOSURE OF HUMAN EYES TO HIGH CONCN OF VAPOR FROM TEAR GAS SHELLS HAS CAUSED CORNEAL EDEMA WITH WRINKLING OF DESCEMET'S MEMBRANE, BUT IN MOST PATIENTS THE EYES...RETURNED TO NORMAL.|DIRECT CONTACT WITH LIQUID...HAS CAUSED PERMANENT CORNEAL SCARRING & OPACIFICATION.|TOXIC BY INGESTION, INHALATION, & SKIN ABSORPTION.

ethyl bromoacetate

Ethyl bromoacetate Use and Manufacturing

Methods of Manufacturing

ESTERIFICATION OF BROMOACETIC ACID WITH ETHYL ALCOHOL IN THE PRESENCE OF SULFURIC ACID|Interaction of bromine and acetic acid in the presence of red phosphorus.|Ethanol and bromoacetic acid (esterification)

Grade: technical

Acetic acid, 2-bromo-, ethyl ester: ACTIVE|ANTIFOULING AGENTS TO CONTROL MARINE ORGANISMS. ETHYL BROMOACETATE (2.1 PPM) IN SEAWATER PREVENTED ADHERENCE OF MYTILUS EDULIS TO TEST MATERIAL, SUCH AS A PIECE OF METAL, & 50% OF MUSSELS WERE REMOVED IN 5 DAYS.

Fire Hazards -> Flammable - 2nd degree, Reactive - 1st degree

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Kovats' RI, non-polar column, isothermal Packed SE-30 880. 150. isothermal Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m Tiess, D.Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe1984, 33, 6-9.
Kovats' RI, non-polar column, isothermal Capillary OV-101 873.4 80. isothermal N2; Column length: 15. m; Column diameter: 0.22 mm Komárek, K.Hornová, L.Churácek, J.Glass capillary gas chromatography of homologous series of esters. Separation of homologous series of esters of halogenated carboxylic acids on a glass capillary column with the non-polar stationary silicone phase OV-101J. Chromatogr.1982, 244, 1, 142-147.

Computed Properties

Molecular Weight:167.00
XLogP3:1.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:165.96294
Monoisotopic Mass:165.96294
Topological Polar Surface Area:26.3
Heavy Atom Count:7
Complexity:62.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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