556-56-9 Usage
Description
Allyl iodide, also known as 3-iodopropene, is an organoiodine compound with the chemical formula CH2=CHCH2I. It is a colorless liquid with a pungent odor and is highly reactive due to the presence of a carbon-carbon double bond and an iodine atom. Its reactivity makes it a versatile building block in organic synthesis.
Uses
Used in Chemical Synthesis:
Allyl iodide is used as a reagent in various chemical reactions, particularly in the cis-double allylation of cyclopropenes when used with allylindium sesquiiodide. This application is crucial for the synthesis of complex organic molecules and the development of new chemical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, allyl iodide is used as a building block for the synthesis of various organic compounds, such as N-alkyl 2-pyrrolidone. ALLYL IODIDE is an important intermediate in the production of pharmaceuticals and other bioactive molecules.
Used in Food Preservation:
Allyl iodide is also used in the synthesis of sorbic acid esters, which are widely used as preservatives in the food industry. These esters help prevent the growth of mold, yeast, and bacteria, thereby extending the shelf life of food products.
Synthesis Reference(s)
Synthetic Communications, 20, p. 41, 1990 DOI: 10.1080/00397919008054613
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 556-56-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 6 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 556-56:
(5*5)+(4*5)+(3*6)+(2*5)+(1*6)=79
79 % 10 = 9
So 556-56-9 is a valid CAS Registry Number.
InChI:InChI=1/C3H5I/c1-2-3-4/h2H,1,3H2
556-56-9Relevant articles and documents
Bis(allyl)aluminum cation, tris(allyl)aluminum, and tetrakis(allyl) aluminate: Synthesis, characterization, and reactivity
Lichtenberg, Crispin,Robert, Dominique,Spaniol, Thomas P.,Okuda, Jun
, p. 5714 - 5721 (2010)
Cationic, neutral, and anionic aluminum allyl compounds were synthesized, and their reactivity toward electrophiles was studied. The THF adduct of the previously elusive tris(allyl)aluminum, [Al(η1-C 3H5)3(THF)] (1), was isolated as an oil. Protonolysis of one allyl ligand in 1 using [NEt3H][BPh4] gave the cationic bis(allyl)aluminum, a fragment of the crystalline [Al(η1-C3H5)2(THF) 3-n]+[BPh4]-·(n+1)THF (n = 0, 1) (2). Single-crystal X-ray diffraction of [Al(η1-C 3H5)2(THF)2]+[BPh 4]- (2a) revealed a tetrahedral aluminum center, while [Al(η1-C3H5)2(THF) 3]+[BPh4]- (2b) contains a trigonal-bipyramidal aluminum center with both allyl ligands in the equatorial plane. The tetrakis(allyl)aluminate K+[Al(η1-C 3H5)4]- (3) was also synthesized from the reaction of 1 with K(C3H5). Reactions of the allyl compounds 1-3 with (i) benzophenone, (ii) allyl halides C 3H5X (X = Cl, Br, I), and (iii) halogen X2 (X = Br, I) showed considerable difference with respect to the ionic charge of the aluminum allyl.
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Datta
, p. 1005 (1914)
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Iodine-mediated rearrangements of diallylsilanes
O'Neil, Gregory W.,Cummins, Elizabeth J.
, p. 3406 - 3409 (2017/08/11)
Diallylsilanes can be made to rearrange upon treatment with I2. Of the silanes tested, diallyldiphenylsilane showed the greatest propensity to undergo this intramolecular carbocation allylation process. After etherification of the initially for
MgI2-Mediated Chemoselective Cleavage of Protecting Groups: An Alternative to Conventional Deprotection Methodologies
Berthet, Mathéo,Davanier, Florian,Dujardin, Gilles,Martinez, Jean,Parrot, Isabelle
supporting information, p. 11014 - 11016 (2015/11/10)
The scope of MgI2 as a valuable tool for quantitative and mild chemoselective cleavage of protecting groups is described here. This novel synthetic approach expands the use of protecting groups, widens the concept of orthogonality in synthetic processes, and offers a facile opportunity to release compounds from solid supports. Amazing MgI2: Protecting groups have had a tremendous positive impact on the art of biomolecule synthesis. In a context in which the use of attractive protecting groups is often limited by harsh deprotection conditions and low chemoselective flexibility, MgI2 offers, by the execution of a very simple protocol, a fresh vision with extensive perspectives.