ALLYL IODIDE

Chemical properties

clear orange, red or red-brown liquid

The Uses of ALLYL IODIDE

Allyl iodide is used as a reagent used with allylindium sesquiiodide in the cis-double allylation of cyclopropenes. It is used in synthesis of other organic compounds such as N-alkyl 2-pyrrolidone, Sorbic acid ester etc,.

Synthesis Reference(s)

Synthetic Communications, 20, p. 41, 1990 DOI: 10.1080/00397919008054613

General Description

A yellow liquid with a pungent odor. Denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. Flash point is less than 75°F. Very irritating to skin, eyes and mucous membranes. Poisonous by ingestion and inhalation. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Darkens on exposure to light and air liberating Iodine [Merck 11th ed. 1989]. Insoluble in water.

Reactivity Profile

ALLYL IODIDE is moderately reactive. Incompatible with strong oxidizing and reducing agents. Also, incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Poison by inhalation and ingestion. Mutation data reported. A powerful irritant. A flammable liquid. Incompatible with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits hghly toxic fumes of I-. See also ALLYL COMPOUNDS and IODIDES.

Purification Methods

Purify allyl iodide in a dark room by washing with aqueous Na2SO3 to remove free iodine, then dry with MgSO4 and distil at 43o/90 mm or at atmospheric pressure to give a very pale yellow liquid. (This material, dissolved in hexane, can be stored in a light-protected tight container at -5o for up to three months before free iodine could be detected, by its colour in the solution.) Store it away from light. [Sibbett & Noyes J Am Chem Soc 75 761 1953, Beilstein 1 H 202, 1 I 84, 1 II 172, 1 III 714, 1 IV 761.]