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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
Molecular Weight:
262.13
MDL Number:
MFCD00134444
MOL File:
768-93-4.mol
MSDS File:
SDS
Last updated:2023-08-11 11:30:03

1-Iodoadamantane Properties

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
FDA UNII XT3Z54Z28A

SAFETY

Risk and Safety Statements

WGK Germany  3

1-Iodoadamantane price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 377198 1-Iodoadamantane 98% 768-93-4 5g $178 2024-03-01 Buy
American Custom Chemicals Corporation HCH0010174 1-IODOADAMANTANE 95.00% 768-93-4 5G $911.99 2021-12-16 Buy
Chemenu CM276462 1-Iodoadamantane 95% 768-93-4 5g $210 2021-12-16 Buy
Crysdot CD13004750 1-Iodoadamantane 95+% 768-93-4 5g $225 2021-12-16 Buy
AHH MT-15813 1-Iodoadamantane 98% 768-93-4 50g $750 2021-12-16 Buy
Product number Packaging Price Buy
377198 5g $178 Buy
HCH0010174 5G $911.99 Buy
CM276462 5g $210 Buy
CD13004750 5g $225 Buy
MT-15813 50g $750 Buy

1-Iodoadamantane Chemical Properties,Uses,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

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IFLAB-BB F0701-0078 1-IODOADAMANTANE 1-Adamantyl iodide Adamantane, 1-iodo- RARECHEM AQ TC 1020 Adamantyl iodide Tricyclo(3.3.1.13,7)decane, 1-iodo- Tricyclo[3.3.1.13,7]decane, 1-iodo- Andrographolide sodium bisulfite NSC 169440 1-Iodoadamantane 98% (3s,5s,7s)-1-iodoadamantane 1IODOADAMANTANE,1 IODOADAMANTANE 768-93-4 C10H15I C20H30O5NaHSO3 Building Blocks Alkyl Halogenated Hydrocarbons Organic Building Blocks Alkyl Halogenated Hydrocarbons Organic Building Blocks Adamantane derivatives