Acetyl bromide

Acetyl bromide Basic information
Product Name:Acetyl bromide
Synonyms:Acetylbrimide;CH3COBr;ethanoylbromide;ACETIC ACID BROMIDE;ACETYL BROMIDE;Acetyl Bromide( Controlled Chemical);AcetylBromideForSynthesis;Acetyl bromide, 98+%
CAS:506-96-7
MF:C2H3BrO
MW:122.95
EINECS:208-061-7
Product Categories:Acid Halides;Carbonyl Compounds;Pharmaceutical Intermediates;Organic Building Blocks
Mol File:506-96-7.mol
Acetyl bromide Structure
Acetyl bromide Chemical Properties
Melting point -96 °C
Boiling point 75-77 °C(lit.)
density 1.663 g/mL at 25 °C(lit.)
vapor density 4.3 (vs air)
vapor pressure 92.2 mm Hg ( 25 °C)
refractive index n20/D 1.45(lit.)
Fp >230 °F
storage temp. Store at <= 20°C.
solubility Miscible with ether, chloroform, benzene and acetone.
form Fuming Liquid
color Clear colorless to dark yellow
OdorAcrid and sharp.
Water Solubility REACTS
Sensitive Moisture Sensitive
Merck 14,82
BRN 1697546
InChIKeyFXXACINHVKSMDR-UHFFFAOYSA-N
CAS DataBase Reference506-96-7(CAS DataBase Reference)
NIST Chemistry ReferenceAcetyl bromide(506-96-7)
EPA Substance Registry SystemAcetyl bromide (506-96-7)
Safety Information
Hazard Codes C
Risk Statements 14-34
Safety Statements 26-36/37/39-45-9-25
RIDADR UN 1716 8/PG 2
WGK Germany 3
RTECS AO5955000
9-21
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29159080
Hazardous Substances Data506-96-7(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Acetyl bromide English
SigmaAldrich English
ACROS English
ALFA English
Acetyl bromide Usage And Synthesis
DescriptionAcetyl bromide is a colourless fuming liquid with pungent odour, is combustible, and turns yellow on exposure to air. It is used as an acetylating agent in the synthesis of fine chemicals, agrochemicals, and pharmaceuticals. It is also used as an intermediate for dyes. Acetylation, a case of acylation, is an organic synthesis process whereby the acetyl group is incorporated into a molecule by substitution for protecting –OH groups.
Chemical PropertiesAcetyl bromide is a colorless, fuming liquid that turns yellow on contact with air. It has a sharp, unpleasant odor. Soluble in benzene, ether and methyl chloride. Reacts violently with water or alcohol.
UsesAcetyl Bromide is used as an acetylating agent in the synthesis of fine chemicals, agrochemicals and pharmaceuticals. It is also used as an intermediate for dyes. Further, it reacts with alcohols and amines to produce acetate esters and acetamides. In addition to this, it is involved in the synthetic process of the anti-HIV agent.
ApplicationAcetyl bromide can be used:
In the quantification of lignin in cell wall residues of Arabidopsis.
In the total synthesis of cinchona alkaloids named quinidine and quinine.
To prepare 9,10-diarylanthracenes and triarylmethanes by reacting with arenes and various aromatic aldehydes using ZnBr2/SiO2.
To prepare glycosyl bromides from free sugars or their peracetates.
PreparationThe preparation of acetyl bromide from acetic acid and bromine in the presence of red and yellow phosphorus.
Reaction: Acetic anhydride was brominated with bromine at 80°C, and then the bromine was added between 95°C and 125°C. About 2.5h. After the addition was completed, reflux was continued for 3h and left overnight. Refined by fractional distillation.
Acetyl bromide may also be prepared by reaction between phosphorus tribromide and acetic acid:
3CH3COOH + PBr3 → 3 CH3COBr + H3PO3
General DescriptionA colorless fuming liquid with a pungent odor. Vapors irritate eyes and mucous membranes. Corrosive to metals and tissue. Density 13.9 lb / gal.
Reactivity ProfileAcetyl bromide decomposes violently upon contact with water, steam, methanol or ethanol to form hydrogen bromide gas and acetic acid. Reacts vigorously with bases, both organic and inorganic. Incompatible with oxidizing agents and alcohols. Produces highly toxic fumes of bromine and carbonyl bromide when heated to decomposition [Sax, 9th ed., 1996, p. 34]. Vapor forms an explosive mixture with air [Kirk-Othmer, 3rd ed., Vol. 1, 1978, p. 162]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Health HazardExposures to acetyl bromide cause abdominal pain, sore throat, cough, burning sensation, shortness of breath, and respiratory distress. Contact with the skin causes pain, redness, blisters, dermatitis, and skin burn, severe deep burns, loss of vision, shock or collapse. The occupational worker may show delayed symptoms and lung edema. The vapor is corrosive to the eyes, the skin, and the respiratory tract. The irritation caused by acetyl bromide may lead to chemical pneumonitis and pulmonary edema, and may cause burns to the respiratory tract. The target organs include the eyes, skin, and the mucous membranes.
Chemical ReactivityReactivity with Water: Reacts violently, forming corrosive and toxic fumes of hydrogen bromide; Reactivity with Common Materials: Attacks and corrodes wood and most metals in the presence of moisture. Flammable hydrogen gas may collect in enclosed spaces; Stability During Transport: Stable if protected from moisture; Neutralizing Agents for Acids and Caustics: Flood with water, rinse with dilute sodium bicarbonate or soda ash solution; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Safety ProfilePoison by ingestion, inhalation, skin contact, and intraperitoneal routes. See also HYDROBROMIC ACID and ACETIC ACID. Violent reaction on contact with water, steam, methanol, or ethanol produces toxic and reactive HBr. When heated to decomposition it emits highly corrosive and toxic fumes of carbonyl bromide and bromine. To fight fire, use dry chemical, CO2
Potential ExposureAcetyl bromide is used as an acetylating agent in the organic synthesis of other chemicals, pesticides, perfume, pharmaceuticals, and it is also used as a dye intermediate.
storageAcetyl bromide should be stored in a tightly sealed container, in a cool, dry, well-ventilated area, away from water and incompatible substances.
ShippingUN1716 Acetyl bromide, Hazard class: 8; Labels: 8-Corrosive material
Purification MethodsBoil acetyl bromide with PBr3/Ac2O for 1hour, then distil the latter off and redistil it. Store it dry. [Burton & Degering J Am Chem Soc 62 227 1940, Beilstein 2 IV 398.] LACHRYMATORY.
IncompatibilitiesAcetyl bromide Vapor may form explosive mixture with air. Instability increases as temperature rises, Contact with moisture, water, steam, alcohols cause a violent reaction releasing corrosive carbonyl bromide, hydrogen bromide, and bromine gases. Incompatible with organic solvents, ethers, oxidizers, and strong bases. Corrodes or attacks most metals and wood in the presence of moisture. Contact with combustibles may cause ignition
Waste DisposalDispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed. Slow addition to sodium bicarbonate solution in a glass or plastic container. Mix slowly in another container containing lots of water. It is inappropriate and possibly dangerous to the environment to dispose of chemical wasteby flushing them down the toilet or discarding them to the trash
PrecautionsAcetyl bromide is combustible and emits irritating or toxic fumes (or gases) in a fire. It should have no contact with naked flames or water. During use, occupational workers should use protective gloves, protective clothing, a face shield or eye protection in combination with breathing protection and should not eat, drink, or smoke. Acetyl bromide decomposes on heating and produces toxic and corrosive fumes, such as hydrogen bromide and carbonyl bromide. It reacts violently with water, methanol, or ethanol to form hydrogen bromide. Acetyl bromide attacks and damages many metals in the presence of water.
Acetyl bromide Preparation Products And Raw materials
Preparation Products4-Bromo-2-methylpyridine-->4-Bromopyridine-2-carboxylic acid-->DL-CARNITINE-->Cefdinir-->ACETYLCHOLINE BROMIDE-->4-(DIMETHYLAMINO)PYRIDINE-2-CARBOXYLIC ACID-->Triphenylmethyl bromide-->Benzyl acetate-->Zalcitabine-->1,5-Diacetoxypentane-->1-(9-ETHYL-9H-CARBAZOL-3-YL)ETHANONE-->4-bromobutan-2-one-->S-N-PROPYL THIOACETATE-->IRON DODECACARBONYL-->5-BROMOPENTYL ACETATE-->BROMOMETHYL ACETATE
Acetyl-resveratrol Acetylspiramycin Acetylcholine Acetaminophen ACETAMINOPHENOL BP/USP Acetylacetone Rocuronium bromide Acetyl chloride Acetyl bromide 2-Acetoxy-2-methylpropionyl bromide Acetylsalicylic acid Acetyl coenzyme A sodium salt Sodium bromate Ethidium bromide Allyl bromide Acetyl bromide, bromo- Methyl bromide BENZOYL BROMIDE

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