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Sodium iodide is widely used for halide exchange (Finkelstein reaction), for example in the conversion of an alkyl chloride, allyl chloride and arylmethyl chloride into their respective iodides, which are precursors for pharmaceutical and fine chemical products. They are used to ehnance the efficiency of the formation of Wittig adducts from less reactive chlorides and bromides. Appropriate prepartions find use as a nutrient supplement. Sodium iodide is used as the precursor to the control agent in ab initio emulsion polymerization. Sodium iodide finds use in the determination of dissolved oxygen in the modified Winkler method, synthesis of the fluorescent dye coppersensor-1 (CS1) for imaging labile copper pools in biological samples, and the cleavage of esters, lactones, carbamates and ethers in combination with chlorotrimethylsilane.
Converts alkyl chlorides or bromides to iodides (Finkelstein reaction). Preferred solvents are acetone or MEK, in which NaI, but not the chloride or bromide, is soluble. See, e.g.: Org. Synth. Coll., 2, 476 (1955); 4, 84 (1963). Activated aryl halides, such as 1-chloro-2,4-dinitrobenzene can be converted to iodides by reaction with NaI in DMF: Org. Synth. Coll., 5, 478 (1973).
Frequently used in catalytic amounts to increase the rate of nucleophilic displacement reactions of alkyl halides and sulfonates; see, for example: Org. Synth. Coll., 9, 46 (1998).
Ethers can be cleaved to ω-iodo esters with a combination of NaI and an acyl chloride: Tetrahedron Lett., 23, 681 (1982). Cleavage of ethers also occurs in the presence of TMS chloride: Angew. Chem. Int. Ed., 20, 690 (1981); J. Org. Chem., 44, 1247 (1979); 48, 3667 (1983). The same combination also reduces benzylic alcohols to arylmethanes: Tetrahedron Lett., 28, 3817 (1987); Bull. Chem. Soc. Jpn., 62, 3537 (1989) and deprotects MEM ethers: Tetrahedron Lett., 25, 1429 (1984); see 2-Methoxyethoxymethyl chloride, L01050.
In combination with Titanium(IV) chloride, 14713, reduction of amine oxides and nitrones occurs: Chem. Ber., 123, 647 (1990). Similarly, sulfoxides are reduced to sulfides: Synthesis, 155 (1991), and mild reductive deoximation can be effected: Synth. Commun., 21,1777 (1991).
Penheiter, A. R.; Russell, S. J.; Carlson, S. K. The Sodium Iodide Symporter (NIS) as an Imaging Reporter for Gene, Viral, and Cell-based Therapies. Curr. Gene Ther. 2012, 12, (1), 33-47.
Tonnar, J.; Lacroix-Desmazes, P. Use of Sodium Iodide as the Precursor to the Control Agent in Ab Initio Emulsion Polymerization. Angew. Chem. Int. Ed. 2008, 47, 1294-1297.
Hazard Statements: H315-H319
Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P264b-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse.