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700-58-3 - 2-Adamantanone, 98% - A14275 - Alfa Aesar

A14275 2-Adamantanone, 98%

CAS Number
700-58-3
Synonyms

Size Price ($) Quantity Availability
5g 38.49
25g 114.40
100g 333.60
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2-Adamantanone, 98%

MDL
MFCD00074737
EINECS
211-847-2

Chemical Properties

Formula
C10H14O
Formula Weight
150.22
Melting point
ca 257° subl.
Solubility
Solubility in methanol is almost transparent.

Applications

It is used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane1 and (+/-)-1-(adamantan-2-yl)-2-propanamine. It is employed in reductive coupling (TiCl3/Li) which gives (adamantylidene)adamantane, an example of a general method for the synthesis of highly-substituted alkenes and in the preparation of highly-substituted alkenes by the Wittig reaction which gives poor yields with adamantanone.

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Sunil Sabbani, et al. Piperidine dispiro-1,2,4-trioxane analogues.Bioorg Med Chem Lett.,2008,18(21), 5804-5808.

E Mariani, et al. (+/-)-1-(Adamantan-2-yl)-2-propanamine and other amines derived from 2-adamantanone.Farmaco Sci.,1980,35(5), 430-40.

Matthew M Meyer and Steven R Kass.Enolates in 3-D: an experimental and computational study of deprotonated 2-adamantanone.J Org Chem.,2010,75(12), 4274-4279.

Reductive coupling (TiCl3/Li) gives (adamantylidene)adamantane, an example of a general method for the synthesis of highly-substituted alkenes: Org. Synth. Coll., 7, 1 (1990).

Preparation of highly-substituted alkenes by the Wittig reaction gives poor yields with adamantanone. The route involving addition of a Grignard or alkyllithium reagent is to be preferred: J. Org. Chem., 54, 1375 (1989).

Other References

Beilstein
1210235
Harmonized Tariff Code
2914.29
TSCA
No
RTECS
AU5018000

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