| | Ethyl bromoacetate Basic information |
| | Ethyl bromoacetate Chemical Properties |
| Melting point | -38 °C | | Boiling point | 159 °C(lit.) | | density | 1.506 g/mL at 25 °C(lit.) | | vapor density | 5.8 (vs air) | | vapor pressure | 2.6 mm Hg ( 25 °C) | | refractive index | n20/D 1.451(lit.) | | Fp | 118 °F | | storage temp. | Store below +30°C. | | solubility | water: insoluble | | form | Liquid | | color | Clear | | Specific Gravity | 1.506 | | Odor | Pungent odour | | Water Solubility | Miscible with ethanol, acetone, benzene and ethyl ether. Immiscible with water. | | BRN | 506456 | | Stability: | Stable. Combustible. Incompatible with strong oxidizing agents, water, strong acids. | | InChIKey | PQJJJMRNHATNKG-UHFFFAOYSA-N | | CAS DataBase Reference | 105-36-2(CAS DataBase Reference) | | NIST Chemistry Reference | Acetic acid, bromo-, ethyl ester(105-36-2) | | EPA Substance Registry System | Acetic acid, 2-bromo-, ethyl ester (105-36-2) |
| | Ethyl bromoacetate Usage And Synthesis |
| Chemical Properties | Ethyl bromoacetate is a clear, colorless to light-yellow liquid and has a pungent odor. It is miscible with ethanol, ether, benzene and with other oxygenated and aromatic solvents, insoluble in water and partially decomposed by water. | | Uses | Ethyl bromoacetate is widely used as an alkylating reagent involved in the Reformatsky reaction to prepare the beta-hydroxy esters by reacting with carbonyl compounds. It is also used for the syntheses of witting reagent, artificial diethylstilbestrol antigen, 3-phenyl-1-naphthol and steroidal thiazolidinone derivatives. It finds applications in the preparation of reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in an aqueous medium which act as a detectable drug carrier. | | 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. | | General Description | 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. Specific gravity of 1.5. | | Air & Water Reactions | Flammable. Insoluble in water. | | Reactivity Profile | 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. | | 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. | | 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. | | Safety Profile | A poison. An irritant to
skin, eyes, and mucous membranes.
Questionable carcinogen with experimental
neoplastigenic data. Flammable liquid when
exposed to heat, flame, and oxidizers. Will
react with water or steam to produce toxic
and corrosive fumes. To fight fire, use water
as a fire blanket. When heated to
decomposition or on contact with acid or
acid fumes, it emits highly toxic fumes of
Br-. See also BROMIDES. | | Potential Exposure | Used for making pharmaceuticals; as
a warning gas in poisonous, odorless gasses; as a tear gas | | Shipping | UN1603 Ethyl bromoacetate, Hazard class: 6.1;
Labels: 6.1-Poisonous materials. | | 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. | | 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. |
| | Ethyl bromoacetate Preparation Products And Raw materials |
| Raw materials | Bromoacetic acid | | Preparation Products | ETHYL 3,3-DIETHOXYPROPIONATE-->METHYL5,5,5-TRIFLUORO-4-OXOPENTANOATE-->ethyl 2-(2-aminothiazol-5-ylthio)acetate-->3-COUMARANONE-->(R)-3-Aminoquinuclidine dihydrochloride-->ETHYL 2-(5-FORMYL-2,4-DIMETHYL-1H-PYRROL-3-YL)ACETATE-->(4-PHENYL-PIPERAZIN-1-YL)-ACETIC ACID-->Rhodanine-3-acetic acid-->3,4-DIMETHYLTHIENO[2,3-B]THIOPHENE-2-CARBALDEHYDE-->2-Phenyl-1H-indole-1-acetic acid ,97%-->3-(4-CHLORO-PHENYL)-PROPIONALDEHYDE-->3,5-DIMETHYL-BENZOFURAN-2-CARBOXYLIC ACID-->3-O-TOLYL-PROPIONALDEHYDE-->6-BROMO-1-BENZOFURAN-2-CARBOXYLIC ACID-->ethyl 2-(2-phenyl-1H-indol-1-yl)acetate-->2-(CARBOXYMETHOXY)BENZOIC ACID-->(S)-(+)-3-Quinuclidinol-->(R)-3-Quinuclidinol hydrochloride-->quinuclidine-3-carboxylic acid-->2-METHYLCYCLOPROPANECARBOXYLIC ACID-->2-Piperazinone-->5-BROMO-1-BENZOFURAN-2-CARBALDEHYDE-->ETHYL METHANESULFONYLACETATE-->Ethyl 3,5-dimethylbenzofuran-2-carboxylate ,95%-->(5-BROMO-1-BENZOFURAN-2-YL)METHANOL-->3-METHYLBENZOFURAN-2-CARBONYL CHLORIDE-->5-BROMO-1-BENZOFURAN-2-CARBOXYLIC ACID-->trans-2-Octen-1-ol-->MORPHOLINE-4-CARBOTHIOAMIDE-->(4-METHYL-PIPERAZIN-1-YL)-ACETIC ACID-->4-(TRIFLUOROMETHYL)PHENOXYACETIC ACID-->GERANIC ACID-->Ethyl(4-butyry-2,3-dichloro)phenoxyacetate-->ETHYL(5-BROMOBENZOFURAN)-2-CARBOXYLATE-->ETHYL 3-AMINOBENZOFURAN-2-CARBOXYLATE-->Ethyl 2-oxocyclopentylacetate-->(4-FLUOROPHENOXY)ACETYL CHLORIDE-->3-METHYLBENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER-->3-CHLOROPHENOXYACETYL CHLORIDE-->4-CHLORO-8-FLUORO-5H-PYRIMIDO[5,4-B]INDOLE |
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