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100277

Sigma-Aldrich

Adamantane

≥99%

Synonym(s):

Tricyclo[3.3.1.13,7]decane

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
281-23-2
Molecular Weight:
136.23
Beilstein:
1901173
EC Number:
206-001-4
MDL number:
MFCD00074719
UNSPSC Code:
12352100
PubChem Substance ID:
24846519
NACRES:
NA.22

Assay

≥99%

form

solid

mp

209-212 °C (subl.) (lit.)

SMILES string

C1[C@H]2C[C@H]3C[C@@H]1C[C@@H](C2)C3

InChI

1S/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2/t7-,8+,9-,10+

InChI key

ORILYTVJVMAKLC-YNFQOJQRSA-N

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Application

Adamantane is the structural backbone of various medicinally important compounds such as amantadine, memantine, saxagliptin and vildagliptin. It is used in the synthesis of adamantine-based dirhodium tetracarboxylate catalyst for carbenoid reactions. It can also be used as a seeding material for the nucleation of nanocrystalline diamond films.

Hazard Statements

H413

Precautionary Statements

P273

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Adamantane?a lead structure for drugs in clinical practice.
Spilovska K, et al.
Current Medicinal Chemistry, 23(29), 3245-3266 (2016)
Vlad Badilita et al.
PloS one, 7(8), e42848-e42848 (2012-09-01)
This article describes the development and testing of the first automatically microfabricated probes to be used in conjunction with the magic angle coil spinning (MACS) NMR technique. NMR spectroscopy is a versatile technique for a large range of applications, but
The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.
Lukas Wanka et al.
Chemical reviews, 113(5), 3516-3604 (2013-02-26)
Diamondoid Hydrocarbons--Delving into Nature's Bounty.
Marchand A P
Science, 299(5603), 52-53 (2003)
Dirhodium tetracarboxylate derived from adamantylglycine as a chiral catalyst for carbenoid reactions.
Reddy R P, et al.
Organic Letters, 8(16), 3437-3440 (2006)
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