Allyl bromide

Chemical Properties

Colorless liquid

Chemical Properties

Allyl bromide is a highly flammable, colorless to light yellow liquid with an unpleasant, pungent odor.

Chemical Properties

Allyl bromide is a clear to light yellow liquid. As an alkylating agent, allyl bromide is used extensively in the synthesis of polymers, pharmaceuticals, allyls, and other organic compounds. Allyl bromide is a clear liquid with an intense, acrid, persistent smell and is flammable. It is insoluble in water, but soluble in alcohol, aether, acetone, carbon tetrachloride, and chloroform. In fact, allyl bromide is used in the synthesis of other allyl compounds, to synthesize dyestuff, spice, and as a curative in the medicine industry. Allyl bromide has a very high mobility in soil. It is also used as a soil fumigant and as a contact poison. Allyl bromide induces unscheduled DNA synthesis in HeLa cells.

Uses

Allyl bromide is used as an alkylating agent in the synthesis of pharmaceuticals, polymers, adhesives, perfumes, biochemicals and other allylic compounds. It is used as precursor for the preparation of allyliczinc bromide by reacting it with zinc. It is also used in the preparation of allylethers like allyl decyl ether, allyl benzyl ether and allyl geranyl ether. It is also used in the preparation of R enantiomer of allyl phenyl carbinol (APC) such as 1-phenyl-3-butene, which is a valuable intermediate for drugs and agro-chemicals.

Uses

Allyl Bromide is used as a reagent in the synthesis of Resveratrol derivatives. Resveratrol (R150000) is a minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet a ggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion a nd progression.

Uses

manufacture of synthetic perfumes, other allyl compounds.

General Description

A clear colorless to light yellow liquid with an irritating unpleasant odor. Flash point 30°F. Irritates eyes, skin, and respiratory system. Toxic by skin absorption. Denser than water and slightly soluble in water.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Allyl bromide decomposes upon heating and exposure to light, forming HBr (a strong reducing agent). Reacts violently with oxidizing agents. Can react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

Hazard

Strong irritant to skin and eyes, flammable, high fire risk. Upper respiratory tract irritant. Ques- tionable carcinogen.

Health Hazard

Inhalation of vapor irritates mucous membranes and causes dizziness, headache, and lung irritation. Contact with liquid irritates eyes and skin. Ingestion causes irritation of mouth and stomach.

Health Hazard

Exposures to allyl bromide cause severe eye and skin burns, irritation to the eyes, skin, and respiratory system. It is harmful when absorbed through the skin or inhaled in the workplace. Laboratory rats exposed for a prolonged period of time developed symptoms of poisoning, such as excessive salivation in a small number of animals, and severe gastric irritation. Vapors of allyl bromide may cause dizziness or suffocation, headache, coughing, and distressed breathing.

Flammability and Explosibility

Highly flammable

Safety Profile

Poison by ingestion and intraperitoneal routes. Mdly toxic by inhalation. Human mutation data reported. See also ALLYL CHLORIDE and ALLYL COMPOUNDS. Dangerous fire and explosion hazard when exposed to heat, flame, or oxidizers. When heated to decomposition it emits toxic fumes of Br-. To fight fire, use alcohol foam, water spray or mist, CO2, dry chemical

Synthesis

Allyl alcohol was synthesized from glycerol and formic acid under inert atmosphere, hydrolysed with NaOH and fractionally distilled to yield the 73% allyl alcohol water azeotrope. This was then reacted with 48% hydrobromic acid and sulfuric acid and the allyl bromide distilled as per the conventional method. It was then redistilled with 3A molecular sieves drying agent to yield the final product which is stored over additional 3A molecular sieves.

Potential Exposure

Used as an insecticide; in the manufacture of resins, fragrances, and other chemicals

storage

Allyl bromide should be stored separate from oxidizing materials and alkalis in a cool, dry, well-ventilated location in tightly closed containers.

Shipping

UN1099 Allyl bromide, Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous materials

Purification Methods

Wash the bromide with NaHCO3 solution then distilled water, dry (CaCl2 or MgSO4), and fractionally distil. Protect it from strong light. [Beilstein 1 IV 754.] LACHRYMATORY, HIGHLY TOXIC and FLAMMABLE.

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. Heat or light exposure may cause decomposition and corrosive vapors.

Waste Disposal

In accordance with 40CFR 165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Precautions

Workers should wear positive pressure self-contained breathing apparatus (SCBA), goggles and a face shield, protective clothing for high concentrations of vapor, chemical protective clothing that is specifi cally recommended by the manufacturer to avoid poisoning. Workers should be careful as allyl bromide reacts with oxidizing materials and alkalis.