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377198 Sigma-Aldrich

1-Iodoadamantane

98%

  • CAS Number 768-93-4

  • Empirical Formula (Hill Notation) C10H15I

  • Molecular Weight 262.13

  •  MDL number MFCD00134444

  •  PubChem Substance ID 24863210

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Properties

Related Categories Alkyl, Building Blocks, Chemical Synthesis, Halogenated Hydrocarbons, Organic Building Blocks More...
InChI Key   PXVOATXCSSPUEM-CHIWXEEVSA-N
assay   98%
mp   75-76 °C (lit.)

Description

General description

1-Iodoadamantane is a haloadamantane. Voltammetric reduction of 1-iodoadamantane at a silver cathode in tetrahydrofuran (THF) and acetonitrile (ACN) is reported to involve a single electron forming a mixture of monomeric and dimeric products. The photoinduced reaction of 1-iodoadamantane in DMSO is reported to afford substitution products on C3, C6, and C8, 1-adamantanol, 1-adamantyl 2-naphthyl ether, and adamantine. The photostimulated reaction of the phthalimide anion with 1-iodoadamantane is reported to yield 3-(1-adamantyl) phthalimide and 4-(1-adamantyl) phthalimide, along with the reduction product adamantane. 1-Iodoadamantane is reported to undergoe photostimulated reaction with the enolate anion of acetone, acetophenone and propiophenone to give admantane and the substitution products.

Application

1-Iodoadamantane is suitable reagent used to evaluate the rate constants for the reduction of haloadamantanes by SmI2 in presence of hexamethylphosphoramide (HMPA) and H2O by GC/MS-analyzed method. It may be used as iodine atom donor for probing the intermediacy of radical to investigate the chemistry of highly reactive, strained systems such as propellane. It may be used as starting reagent in the synthesis of N-(1-adamantyl)acetamide via nucleophilic substitution. It may be employed in the free-radical carbonylation reactions with alkenes.

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis

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Protocols & Articles
Peer-Reviewed Papers
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References

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