187836
1,3-Dimethyladamantane
≥99%
Synonym(s):
1,3-Dimethyltricyclo[3.3.1.13,7]decane
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About This Item
Empirical Formula (Hill Notation):
C12H20
CAS Number:
Molecular Weight:
164.29
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥99%
form
liquid
refractive index
n20/D 1.478 (lit.)
density
0.886 g/mL at 25 °C (lit.)
SMILES string
C[C@]12C[C@@H]3C[C@H](C1)C[C@@](C)(C3)C2
InChI
1S/C12H20/c1-11-4-9-3-10(5-11)7-12(2,6-9)8-11/h9-10H,3-8H2,1-2H3/t9-,10+,11-,12+
InChI key
CWNOIUTVJRWADX-BKUVIOGVSA-N
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Related Categories
General description
1,3-Dimethyladamantane undergoes C-H insertion reaction with phenylchlorocarbene. It reacts with with molecular oxygen in the presence of N-hydroxyphthalimide combined with cobalt salts to yield 3,5-dimethyladamantan-1-ol and 5,7-dimethyladamantane-1,3-diol.
Application
1,3-Dimethyladamantane was used in the synthesis of 1,3-dibromo-5,7-dimethyladamantane.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Flam. Liq. 3
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
127.4 °F - closed cup
Flash Point(C)
53 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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R A Moss et al.
Organic letters, 1(5), 819-822 (2005-08-25)
[structure: see text] Phenylchlorocarbene inserts into the tertiary CH bonds of 1,3-dimethyladamantane and 1-X-adamantanes (X = H, OMe, COOMe, Cl, CN). There is a good correlation between the relative rate constants for these insertions and the inductive substituent constants, sigma1(X)
The synthesis of 3-amino-3-methylbicyclo [3.3. 1] nonanes: Endo-selectivity in the Ritter reaction of 1, 3, 5, 7a-tetramethylbicyclo [3.3. 1] nonan-3-ol.
Mishnev AF.
Journal of the Chemical Society. Perkin Transactions 1, 23, 3527-3530 (1999)
Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with transition metal salts.
Ishii Y, et al.
Tetrahedron Letters, 37(28), 4993-4996 (1996)
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