General Description
A clear, colorless liquid (b.p. 318°F). Flash point 47°C. 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. Specific gravity of 1.5.
Reactivity Profile
ETHYL BROMOACETATE(105-36-2) 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.
Air & Water Reactions
Flammable. Insoluble in water.
Hazard
Toxic by ingestion, inhalation, and skin
absorption; strong irritant.
Health Hazard
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.
Potential Exposure
Used for making pharmaceuticals; as
a warning gas in poisonous, odorless gasses; as a tear gas
Fire Hazard
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. 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.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy
Shipping
UN1603 Ethyl bromoacetate, Hazard class: 6.1;
Labels: 6.1-Poisonous materials.
Incompatibilities
Vapor may form explosive mixture with
air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep
away from alkaline materials, strong bases, strong acids,
oxoacids, epoxides, and reducing agents. Esters are generally incompatible with nitrates. Moisture may cause hydrolysis or other forms of decomposition.
Description
Ethyl bromoacetate is a clear, colorless tolight-yellow liquid. Molecular weight = 167.02; Boilingpoint = 159℃. Freezing point ≤-20℃; Flashpoint = 48℃. Hazard Identification (based on NFPA-704 MRating System): Health 2, Flammability 2, Reactivity 0.Insoluble in water
Chemical Properties
Ethyl bromoacetate is a clear, colorless to light-yellow liquid and has a pungent odor. It is insoluble in water, but is soluble in acetone and benzene (Lide, 1999; Lewis, 1997). Ethyl bromoacetate is miscible with ethanol, ethyl ether, and with other oxygenated and aromatic solvents (Ashford, 1994; Lide, 1999). It is partially decomposed by water (Lewis, 1997).
Uses
Ethyl Bromoacetate, is used in the synthesis of metabolites of carcinogenic PAHs. Used in the preparation of steroidal antiestrogens through cyclic condensation. A reactant in the preparation of antim
icrobial and antioxidant coumarinyloxymethyl-thiadiazolone.
Application
Ethyl Bromoacetate is used as a synthetic organic chemical intermediate as well as a pharmaceutical and agricultural intermediate. It is used in the synthesis of metabolites of carcinogenic PAHs. It is also used in the preparation of steroidal antiestrogens through cyclic condensation. Ethyl Bromoacetate is a reactant in the preparation of antim icrobial and antioxidant coumarinyloxymethyl-thiadiazolone.
Preparation
Ethyl bromoacetate is commonly synthesized by sulfuric acid catalyzed esterification of monobromoacetic acid (MBAA). After reaction completion, excess acid is washed out and the product purified via distillation under reduced pressure if necessary (Stenger, 1978; Korhonen, 1984).
Reactions
Ethyl bromoacetate on derivatisation reaction with p-t-butyl calix[4]arene yields 1,3-diester substituted calix[4]arene. It also undergoes Suzuki type cross-coupling reactions with arylboronic acids cocatalyzed by copper(I) oxide.
storage
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-ventilated area away from oxidizers, strong acids, strongbases, reducing agents, heat, and sources of ignition. Wherepossible, automatically pump liquid from drums or otherstorage containers to process containers.
Purification Methods
Wash the ester with saturated aqueous Na2CO3 (three times), 50% aqueous CaCl2 (three times) and saturated aqueous NaCl (twice). Dry with MgSO4, CaCl2 or CaCO3, and distil it. [Beilstein 2 IV 527.] LACHRYMATORY.