394688
2-(1-Adamantyl)-4-methylphenol
99%
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About This Item
Fórmula empírica (notación de Hill):
C17H22O
Número de CAS:
Peso molecular:
242.36
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
99%
form
powder
mp
128-130 °C (lit.)
SMILES string
Cc1ccc(O)c(c1)C23C[C@H]4C[C@H](C[C@H](C4)C2)C3
InChI
1S/C17H22O/c1-11-2-3-16(18)15(4-11)17-8-12-5-13(9-17)7-14(6-12)10-17/h2-4,12-14,18H,5-10H2,1H3/t12-,13+,14-,17-
InChI key
XHLJIHBDAJFXBE-ZZNDEYBLSA-N
Categorías relacionadas
General description
2-(1-Adamantyl)-4-methylphenol is a 2-adamantylphenol derivative. It has been synthesized by the adamantylation of p-cresol with 1-adamantanol. The structure has been confirmed by 1H and 13C NMR.
Application
2-(1-Adamantyl)-4-methylphenol is a suitable starting reagent used in the synthesis of 2-(1-adamantyl)-4-methylthiophenol. It may also be used in the synthesis of 3-(1-adamantyl)-2-hydroxy-5-methylbenzaldehyde by reacting with urotropin. It may be used in the synthesis of adamantyl-substituted chromium(III) complex, a catalyst for enantioselective hetero-Diels-Alder reactions.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Synthesis of 2, 4-disubstituted thiophenols and solid state structures of thiocarbamate precursors.
Flores-Figueroa A, et al
Journal of the Brazilian Chemical Society, 16.3A, 397-403 (2005)
Highly Enantio-and Diastereoselective Hetero-Diels?Alder Reactions Catalyzed by New Chiral Tridentate Chromium (iii) Catalysts.
Dossetter AG, et al.
Angewandte Chemie (International Edition in English), 38(16), 2398-2400 (1999)
Nan Wang et al.
Beilstein journal of organic chemistry, 8, 227-233 (2012-03-17)
A clean process has been developed for the synthesis of 2-adamantylphenol derivatives through adamantylation of substituted phenols with adamantanols catalyzed by commercially available and recyclable ion-exchange sulfonic acid resin in acetic acid. The sole byproduct of the adamantylation reaction, namely
Reactions of 2-hydroxymethylphenols with Lawesson's reagent.
Osyanin VA, et al
Chemistry of Heterocyclic Compounds, 47(7), 901-905 (2011)
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