1-Iodoadamantane

ChemicalBook > CAS DataBase List > 1-Iodoadamantane

Product Name: 1-Iodoadamantane
CAS No.: 768-93-4
Chemical Name: 1-Iodoadamantane
Synonyms: NSC 169440;1-IODOADAMANTANE;Adamantyl iodide;1-Adamantyl iodide;RARECHEM AQ TC 1020;Adamantane, 1-iodo-;IFLAB-BB F0701-0078;1-Iodoadamantane 98%;(3s,5s,7s)-1-iodoadamantane;Andrographolide sodium bisulfite
CBNumber: CB2191577
Molecular Formula: C10H15I
Formula Weight: 262.13
MOL File: 768-93-4.mol

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1-Iodoadamantane Property

Melting point:: 75-76 °C(lit.)
Boiling point:: 265.7±9.0℃ (760 Torr)
Density: 1.63±0.1 g/cm3 (20 ºC 760 Torr)
refractive index: 1.6610 (estimate)
Flash point:: 115.9±13.1℃
storage temp.: 2-8°C(protect from light)
solubility: DMSO: 52 mg/mL (198.37 mM);;
Stability:: Stable, but light and moisture sensitive. Incompatible with strong oxidizing agents.
InChI: InChI=1S/C10H15I/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
InChIKey: PXVOATXCSSPUEM-UHFFFAOYSA-N
SMILES: C12(I)CC3CC(CC(C3)C1)C2

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 377198
Product name: 1-Iodoadamantane
Purity: 98%
Packaging: 5g
Price: $178
Updated: 2024/03/01

American Custom Chemicals Corporation

Product number: HCH0010174
Product name: 1-IODOADAMANTANE
Purity: 95.00%
Packaging: 5G
Price: $911.99
Updated: 2021/12/16

Chemenu

Product number: CM276462
Product name: 1-Iodoadamantane
Purity: 95%
Packaging: 5g
Price: $210
Updated: 2021/12/16

Crysdot

Product number: CD13004750
Product name: 1-Iodoadamantane
Purity: 95+%
Packaging: 5g
Price: $225
Updated: 2021/12/16

AHH

Product number: MT-15813
Product name: 1-Iodoadamantane
Purity: 98%
Packaging: 50g
Price: $750
Updated: 2021/12/16

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1-Iodoadamantane Chemical Properties,Usage,Production

Chemical Properties

solid

Uses

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 2766, 1983 DOI: 10.1021/jo00164a026

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.

Purification Methods

Dissolve the iodide in Et2O, shake with aqueous NaHSO3, aqueous K2CO3, and H2O, dry (Na2SO4), evaporate and recrystallise it from MeOH at -70o (to avoid alcoholysis) to give white crystals. [Schleyer & Nicholas J Am Chem Soc 83 2700 1961, lit m of 151-152.5o is incorrect.] Also purify by recrystallisation from pet ether (40-60oC) followed by rigorous drying and repeated sublimation. [Beilstein 5 IV 470.]

1-Iodoadamantane Preparation Products And Raw materials

Raw materials

Preparation Products

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768-93-4, 1-IodoadamantaneRelated Search:

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