ChemicalBook CAS DataBase List Ninhydrin hydrate

Ninhydrin hydrate synthesis

9synthesis methods

Product Name:Ninhydrin hydrate
CAS Number:485-47-2
Molecular formula:C9H6O4
Molecular Weight:178.14

The synthesis of Ninhydrin hydrate is as follows:
A sealed-pressurised reaction vessel (5mL) equipped with a magnetic stirrer was charged with indan-1-one (1equiv), selenium dioxide (3.1equiv) and dioxane/water (3mL/0.3mL). It was then irradiated in a Biotage Initiator Microwave synthesizer 2.0 440W with microwave heating to 180°C with a maximum of 400W for 5min. Then, the vessel was rapidly forced-air cooled to room temperature. The mixture was transferred into a round bottom flask, and the vessel washed with acetone. Silica was added to prepare a solid deposit. The volatile solvents were then evaporated in vacuo before purification by flash chromatography (ethyl acetate/cyclohexane) to afford the corresponding ninhydrin.
synthesis of Ninhydrin hydrate.png

83-33-0
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$6.00/5g

485-47-2
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$9.00/1g

Yield:485-47-2 84%

Reaction Conditions:

with selenium(IV) oxide;water in 1,4-dioxane at 180; for 0.0833333 h;Sealed tube;Microwave irradiation;Temperature;

Steps:

General experimental procedure for the synthesis of the ninhydrins (2):

General procedure: A sealed-pressurised reaction vessel (5mL) equipped with a magnetic stirrer was charged with indan-1-one (1equiv), selenium dioxide (3.1equiv) and dioxane/water (3mL/0.3mL). It was then irradiated in a Biotage Initiator Microwave synthesizer 2.0 440W with microwave heating to 180°C with a maximum of 400W for 5min. Then, the vessel was rapidly forced-air cooled to room temperature. The mixture was transferred into a round bottom flask, and the vessel washed with acetone. Silica was added to prepare a solid deposit. The volatile solvents were then evaporated in vacuo before purification by flash chromatography (ethyl acetate/cyclohexane) to afford the corresponding ninhydrin.

References:

Marminon, Christelle;Nacereddine, Abdelhamid;Bouaziz, Zouhair;Nebois, Pascal;Jose, Joachim;Le Borgne, Marc [Tetrahedron Letters,2015,vol. 56,# 14,p. 1840 - 1842] Location in patent:supporting information