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143367

Sigma-Aldrich

1-Adamantyl isothiocyanate

99%

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About This Item

Formula empirica (notazione di Hill):
C11H15NS
Numero CAS:
4411-26-1
Peso molecolare:
193.31
Numero CE:
224-564-4
Numero MDL:
MFCD00074736
Codice UNSPSC:
12352100
ID PubChem:
24848581
NACRES:
NA.22

Saggio

99%

Punto di fusione

166-168 °C (lit.)

Gruppo funzionale

isothiocyanate

Stringa SMILE

S=C=NC12CC3CC(CC(C3)C1)C2

InChI

1S/C11H15NS/c13-7-12-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-6H2/t8-,9+,10-,11-
YPKFLUARLJRPQM-BIBSGERRSA-N

Descrizione generale

1-Adamantyl isothiocyanate undergoes nucleophilic addition reaction with pyrrolidine, piperidine, 3-hydroxypiperidine and 4-hydroxypiperidine to yield N′,N′-disubstituted N-(1-adamantyl)-thiourea derivatives.

Applicazioni

1-Adamantyl isothiocyanate was used in the synthesis of:
  • tris(2-mercapto-1-adamantylimidazolyl)hydroborato ligand
  • 1-adamantyl-3-(2-(7-methoxy-1,2,3,4-tetrahydroacridin-9-ylamino)alkane)thiourea 2,3-dihydroxysuccinates

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302 + H312 + H332,H315,H319,H335

Classi di pericolo

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
MKBL6292V
00324EH
08407KB

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A Kreutzberger et al.
Arzneimittel-Forschung, 27(5), 969-972 (1977-01-01)
By nucleophilic addition of pyrrolidine (2a), piperidine (2b), 3-hydroxypiperidine (2c), and 4-hydroxypiperidine (2d) on 1-adamantyl-isothiocyanate (1), the N',N'-disubstituted N-(1-adamantyl)-thiourea derivatives 3a, 3b, 3c, and 3d are accessible. Particularly 3d exhibits remarkable antiviral activity vaccinia and herpes virus.
Kevin Yurkerwich et al.
Inorganic chemistry, 50(24), 12284-12295 (2011-09-29)
The tris(2-mercapto-1-adamantylimidazolyl)hydroborato ligand, [Tm(Ad)], has been synthesized via the reaction of 1-adamantyl-2-mercaptoimidazole with MBH(4) (M = Li, K). [Tm(Ad)]M has been used to synthesize a variety of compounds of the main-group and transition elements, including [Tm(Ad)]ZnI, {[Tm(Ad)]GaI}[GaI(4)], {[Tm(Ad)]GaCl}[GaCl(4)], {[Tm(Ad)]GaGa[Tm(Ad)]}[GaCl(4)](2), {[Tm(Ad)](2)In}[InI(4)]
Van Hien Pham et al.
Molecules (Basel, Switzerland), 25(2) (2020-01-17)
Reaction of 4-(1-adamantyl)-3-thiosemicarbazide (1) with numerous substituted acetophenones and benzaldehydes yielded the corresponding thiosemicarbazones containing adamantane skeletons. The synthesized compounds were evaluated for their in vitro activities against some Gram-positive and Gram-negative bacteria, and the fungus Candida albicans, and cytotoxicity
Katarina Spilovska et al.
Molecules (Basel, Switzerland), 18(2), 2397-2418 (2013-02-23)
A structural series of 7-MEOTA-adamantylamine thioureas was designed, synthesized and evaluated as inhibitors of human acetylcholinesterase (hAChE) and human butyrylcholinesterase (hBChE). The compounds were prepared based on the multi-target-directed ligand strategy with different linker lengths (n = 2-8) joining the

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