ChemicalBook CAS DataBase List 1-ADAMANTYL ISOTHIOCYANATE

1-ADAMANTYL ISOTHIOCYANATE synthesis

12synthesis methods

Product Name:1-ADAMANTYL ISOTHIOCYANATE
CAS Number:4411-26-1
Molecular formula:C11H15NS
Molecular Weight:193.31

768-94-5
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$38.10/5g

103-72-0
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$10.00/1g

4411-26-1
86 suppliers
$44.00/1 g

Yield: 80%

Reaction Conditions:

in toluene at 110; for 3 h;

Steps:

1-Isothiocyanatoadamantane (1).
Phenyl isothiocyanate, 7.84 g (0.058 mol), was added to a solution of 10.57 g (0.07 mol) of adamantan-1-amine in 150 mL of toluene, and the mixture was heated for 3 h at 110°C. When the reaction was complete, the solvent was distilled off, and the residue was recrystallized from ethanol. Yield 11.0 g (80%), mp 167-169°C [9]. ¹H NMR spectrum, δ, ppm: 1.41-2.18 m (15H). ¹³C NMR spectrum, δ_C, ppm: 29.3 (C3, C5, C7), 35.6 (C4, C6, C10), 43.8 (C2, C8, C9), 58.5 (C1), 129.4 (NCS). Mass spectrum, m/z (I_rel, %): 193 (10) [M]⁺, 135 (100) [Ad]⁺.

References:

Burmistrov;Butov;Pitushkin [Russian Journal of Organic Chemistry,2015,vol. 51,# 12,p. 1795 - 1796][Zh. Org. Khim.,2015,vol. 51,# 12,p. 1828 - 1829,2]