Hydrogen Iodide - Breton - Major Reference Works - Wiley Online Library

(electrophilic hydriodination of alkenes and alkynes;^3-10 cleavage of epoxides,¹^b^,^{11, 12} ethers, and acetals;¹³ conversion of alcohols to iodides;^14-17 reducing agent for many groups including quinones,^{24, 25} α-diketones,²³ α-ketols,²³ α-halo ketones,¹⁹ α-diazo ketones,²² and sulfoxides;³⁰ reductive cyclization of keto acids^{27, 28})

Alternate Name: hydriodic acid.

Physical Data: 57% aqueous solution: bp 127 °C; d 1.70 g cm⁻³.

Solubility: sol most common organic solvents.

Form Supplied in: compressed gas; colorless 57% aq solution; widely available.

Preparative Methods: from the reaction of tetrahydronaphthalene with I₂;² can be generated in situ (a) from Me₃SiCl and NaI in the presence of water,³ (b) from I₂ and activated alumina,⁴ (c) from KI and H₃PO₄,⁵ and (d) from Et₂PhN·BI₃ and AcOH.⁶

Purification: distillation of the aqueous azeotrope; concentrated solutions can be regenerated after long storage by treatment with hypophosphorous acid.

Handling, Storage, and Precautions: store protected from air and light at or below rt. Highly corrosive and toxic. This reagent should be handled in a fume hood.

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