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768-95-6 - 1-Adamantanol, 99% - 1-Hydroxyadamantane - A10209 - Alfa Aesar

A10209 1-Adamantanol, 99%

CAS Number
768-95-6
Synonyms
1-Hydroxyadamantane

Size Price ($) Quantity Availability
10g 28.43
50g 114.30
250g 457.60
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1-Adamantanol, 99%

MDL
MFCD00074729
EINECS
212-202-8

Chemical Properties

Formula
C10H16O
Formula Weight
152.24
Melting point
ca 245° subl.
Solubility
Soluble in ethanol , methanol, and diethyl ether. Partly miscible in water.

Applications

1-Adamantanol was used in the preparation of 1,3-adamantanediol. It is used in the manufacture of synthetic adamantane derivatives and adapalene.

Notes

Incompatible with oxidizing agents. Store in a cool, dry condition in well sealed containers.

Literature References

Koichi Mitsukura; Hiromu Sakamoto; Haruka Kubo; Toyokazu Yoshida; Toru Nagasawa. Bioconversion of 1-adamantanol to 1,3-adamantanediol usingStreptomycessp. SA8 oxidation system. Journal of Bioscience and Bioengineering. 2010, 109 (6), 550-553.

Motowo Yamaguchi; Hiroyuki Kousaka; Shinichi Izawa; Yoshiki Ichii; Takashi Kumano; Dai Masui; Takamichi Yamagishi. Syntheses, characterization, and catalytic ability in alkane oxygenation of chloro(dimethyl sulfoxide)ruthenium(II) complexes with tris(2-pyridylmethyl)amine and its derivatives. Inorganic Chemistry. 2006, 45 (20), 8342-8354.

Carboxyl groups of amino acids have been protected as 1-adamantyl esters via the amino acid tosylate and dimethyl sulfite. The group is readily cleaved with TFA under mild conditions: Synthesis, 1355 (1996). Has also been applied in blocking the ß-carboxyl group of aspartic acid in peptide synthesis; the 1-adamantyl ester is prepared using DCC-DMAP: J. Chem. Soc., Perkin 1, 2129 (1988). See also Appendix 6.

Thiol groups may also be protected by formation of the thioether in TFA. Cleavage is by means of Hg(II) salts: Chem. Pharm. Bull., 26, 1576 (1978).

Reaction with Hydrogen fluoride pyridine complex, L17117, gives 1-fluoroadamantane, a general method for conversion of sec- and tert-alcohols to fluoroalkanes: Org. Synth. Coll., 6, 628 (1988).

Other References

Beilstein
1903952
Harmonized Tariff Code
2906.19
TSCA
No
RTECS
AU4980000

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