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Thermo Scientific Chemicals
2-Adamantanone, 98%
CAS: 700-58-3 | C10H14O | 150.221 g/mol
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Catalog number A14275.14
also known as A14275-14
Price (USD)
144.65
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Quantity:
25 g
Price (USD)
144.65
Online Exclusive
161.00Save 16.35 (10%)
Each
Chemical Identifiers
CAS700-58-3
IUPAC Nameadamantan-2-one
Molecular FormulaC10H14O
InChI KeyIYKFYARMMIESOX-UHFFFAOYSA-N
SMILESO=C1C2CC3CC(C2)CC1C3
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Specification SheetIt 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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Solubility in methanol is almost transparent.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
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.
Solubility
Solubility in methanol is almost transparent.
Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
RUO – Research Use Only
General 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).