Ethyl bromoacetate

Other Classes -> Halogenated Esters

Flammable agents - 2nd degree

1.5032 @ 20 °C/20 °C

1.5032 @ 20°C

Insoluble in water, soluble in acetone, miscible in ethanol and ethyl ether.

Sol in benzene and alcohol

Miscible in oxygenated and aromatic solvents

48 °C

118 °F (48 °C) (CLOSED CUP)

168.5 °C

158.8 °C @760 [mm Hg]

3.37 [mmHg]

2.6 [mm Hg] @25 °C

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.6% (1 of 164) of reports.

Danger

H226 (93.3%): Flammable liquid and vapor [Warning Flammable liquids]

Chemical: Acetic acid, bromo-, ethyl ester

Status: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18025

Restricted substance: Ethyl bromoacetate

Ethyl bromoacetate: HSNO Approval: HSR004469 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

A skin, eye, and mucous membrane irritant; Contact with liquid can cause corneal burns; [HSDB] A lachrymator and a strong skin irritant; [CAMEO] Highly toxic; [Quick CPC] A lachrymator--exposure to 8 ppm for more than 1 minute is unbearable; [CHEMINFO] Inhalation of high concentrations may produce acute pneumonitis and pulmonary edema; [MSDSonline] See Ethyl chloroacetate.

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.

/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.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

General First Aid:

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.

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.

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

Immediate precautionary measure

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

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).

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627)

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.

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.

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.

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

Used as a tear gas in the past; Also used as a warning odorant in toxic, odorless gases and to make pharmaceuticals and other chemicals; [HSDB]

HAS BEEN EMPLOYED AS TEAR GAS

CHEM INT & REACTANT IN SYNTH OF AN ANALGESIA

CHEM INT, EG, FOR PHARMACEUTICALS & BETA-KETO ACIDS; LACRIMATOR OR WARNING AGENT FOR POISONOUS, ODORLESS GASES

In World War I, ethyl bromoacetate was used as a lachrymatory agent and tear gas agent for chemical warfare. It was also later used as a riot control agent. Today it is mostly used in organic synthesis as an alkylating agent. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

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)

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.