677-69-0 | Heptafluoroisopropyl iodide

CAS:677-69-0 | Heptafluoroisopropyl iodide ,Description

Heptafluoroisopropyl iodide (HFI) is an organofluoride compound with the chemical formula C3F7I. It is a colorless liquid and is a halogenated derivative of isopropyl alcohol. HFI is used in organic synthesis and is a versatile reagent in the laboratory. It is used in the synthesis of a variety of compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. HFI has also been used to study the mechanism of action of drugs and to develop new chemotherapeutic agents.
 

Scientific Research Applications

1. Catalyst in Organic Synthesis

Heptafluoroisopropyl iodide (iC3F7I) has been utilized as both a mild oxidant and radical initiator in the Ru-catalyzed meta-C-H benzylation of arenes. This process exhibits excellent site-selectivity and tolerates a wide range of functional groups, providing an innovative strategy for synthesizing various diarylmethane moieties (Li, Fang, Huang, & Shi, 2017).

2. Synthesis of Perfluoroalkyl Iodides

iC3F7I plays a critical role in the continuous process for preparing perfluoroalkyl iodides. This process involves thermal telomerization of tetrafluoroethylene by iC3F7I in a tubular reactor, offering a method to reduce the proportion of undesirable heavy telomers (Bertocchio, Lacote, & Verge, 1998).

3. Oxidative Coupling in Organic Synthesis

iC3F7I is used as an oxidant in the Ni(II)-catalyzed oxidative coupling between C(sp(2))-H in benzamides and C(sp(3))-H in toluene derivatives. The method displays broad scope and high functional group compatibility, allowing toluene derivatives to be used as coupling partners (Aihara, Tobisu, Fukumoto, & Chatani, 2014).

4. Gas Phase Reactions

The gas phase reaction of heptafluoroisopropyl radicals with carbon tetrachloride, using the photolysis of iC3F7I, provides insights into radical reaction mechanisms. This study contributes to the understanding of Arrhenius parameters for chlorine abstraction from various compounds (de Vöhringer & Staricco, 1986) .

5. Copper(I)-mediated Heptafluoroisopropylation

iC3F7I is employed in copper(I)-mediated heptafluoroisopropylation of aryl halides, using copper(I) carboxylates and a bis(heptafluoroisopropyl)zinc reagent. This process is significant for simple synthetic operations and offers a pathway to heptafluoroisopropyl arene derivatives (Ono, Yokota, Ito, & Mikami, 2019).

More Information