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Ethyl bromoacetate

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CAS:105-36-2
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CAS:105-36-2
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CAS:105-36-2
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CAS:105-36-2
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Ethyl bromoacetate Basic information
Product Name:Ethyl bromoacetate
Synonyms:ethylbromacetate;ethylbromoethanoate;ethylmonobromoacetate;ethoxycarbonylmethylbromide;Ethyl bromoacetate 95+ %;ETHYL BROMOACETATE;ETHYL-2-BROMOETHANOATE;EthylBromoacetateForSynthesis
CAS:105-36-2
MF:C4H7BrO2
MW:167
EINECS:203-290-9
Product Categories:Esters;C2 to C5;Carbonyl Compounds;Pharmaceutical Intermediates;Organics;105-36-2;bc0001
Mol File:105-36-2.mol
Ethyl bromoacetate Structure
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 Gravity1.506
OdorPungent odour
Water Solubility Miscible with ethanol, acetone, benzene and ethyl ether. Immiscible with water.
BRN 506456
Dielectric constant9.75
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, water, strong acids.
InChIKeyPQJJJMRNHATNKG-UHFFFAOYSA-N
CAS DataBase Reference105-36-2(CAS DataBase Reference)
NIST Chemistry ReferenceAcetic acid, bromo-, ethyl ester(105-36-2)
EPA Substance Registry SystemAcetic acid, 2-bromo-, ethyl ester (105-36-2)
Safety Information
Hazard Codes T+
Risk Statements 26/27/28
Safety Statements 26-45-7/9-1/2
RIDADR UN 1603 6.1/PG 2
WGK Germany 1
RTECS AF6000000
19
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29159080
Hazardous Substances Data105-36-2(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Bromoacetic acid ethyl ester English
SigmaAldrich English
ACROS English
ALFA English
Ethyl bromoacetate Usage And Synthesis
DescriptionEthyl 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 PropertiesEthyl 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.
UsesEthyl 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.
ApplicationEthyl 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.
PreparationEthyl 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).
ReactionsEthyl 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 DescriptionEthyl 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 ReactionsFlammable. Insoluble in water.
Reactivity ProfileEthyl 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.
HazardToxic by ingestion, inhalation, and skin absorption; strong irritant.
Health HazardTOXIC; 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 HazardHIGHLY 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 ProfileA 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 ExposureUsed for making pharmaceuticals; as a warning gas in poisonous, odorless gasses; as a tear gas
First aidIf this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24- 48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray
storageColor 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.
ShippingUN1603 Ethyl bromoacetate, Hazard class: 6.1; Labels: 6.1-Poisonous materials.
Purification MethodsWash 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.
IncompatibilitiesVapor 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 materialsBromoacetic acid
Preparation ProductsEthyl 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
Tag:Ethyl bromoacetate(105-36-2) Related Product Information
Ethanol 2-Ethoxyethanol Ethyl propionate Dimethyl succinate Ethyl chloroacetate Ethylparaben Tris(trimethylsilyl)phosphate Ethyl phenylacetate Ethyl acetate Ethyl cyanoacetate Ethyl formate Bromoacetic acid Trinexapac-ethyl Methyl acrylate ISOXADIFEN-ETHYL 1,5-Dibromopentane tert-Butyl 2-bromo-2-methylpropanoate Methyl bromoacetate