377198
1-Iodoadamantane
98%
Sinônimo(s):
1-Adamantyl iodide, 1-Iodotricyclo[3.3.1.13,7]decane, Adamantyl iodide
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About This Item
Fórmula empírica (Notação de Hill):
C10H15I
Número CAS:
Peso molecular:
262.13
Número MDL:
Código UNSPSC:
12352100
ID de substância PubChem:
NACRES:
NA.22
Produtos recomendados
Ensaio
98%
Formulário
solid
pf
75-76 °C (lit.)
grupo funcional
iodo
cadeia de caracteres SMILES
IC12C[C@H]3C[C@H](C[C@H](C3)C1)C2
InChI
1S/C10H15I/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2/t7-,8+,9-,10-
chave InChI
PXVOATXCSSPUEM-CHIWXEEVSA-N
Descrição geral
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.
Aplicação
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.
Código de classe de armazenamento
11 - Combustible Solids
Classe de risco de água (WGK)
WGK 3
Ponto de fulgor (°F)
Not applicable
Ponto de fulgor (°C)
Not applicable
Equipamento de proteção individual
Eyeshields, Gloves, type N95 (US)
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Photostimulated reaction of 1-iodoadamantane with carbanionic nucleophiles in DMSO by the SRN1 mechanism.
Borosky GL, et al.
The Journal of Organic Chemistry, 55(12), 3705-3707 (1990)
Juan E Argüello et al.
The Journal of organic chemistry, 68(6), 2362-2368 (2003-03-15)
The fluorescent excited state of the 2-naphthoxide ion (1) is quenched by aliphatic and aromatic halides according to an electron-transfer mechanism, with generation of the corresponding alkyl and aryl radicals by a concerted or consecutive C-X bond fragmentation reaction. Whereas
Dimerization of Cubene. 1-Iodoadamantane as a Probe for Radical Intermediates.
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Journal of the American Chemical Society, 117(29), 7652-7656 (1995)
Rate study of haloadamantane reduction by samarium diiodide.
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J. Chin. Chem. Soc., 49(6), 969-973 (2002)
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Ultrasonics sonochemistry, 14(5), 502-508 (2007-01-17)
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