2-bromo-1,3-indandione
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | 2-bromo-1,3-indandione | |||||||||||||||
other names |
2-bromo-1,3-dioxoindane |
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Molecular formula | C 9 H 5 BrO 2 | |||||||||||||||
Brief description |
light yellow solid |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 225.04 g mol −1 | |||||||||||||||
Physical state |
firmly |
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Melting point |
118-120 ° C |
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safety instructions | ||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
2-Bromo-1,3-indanedione is a chemical compound that belongs to both the diketones and the halogen aromatic compounds .
presentation
2-Bromo-1,3-indanedione can be carried out by bromination of 1,3-indanedione with bromine . The reaction takes place via the enol form of indanedione.
properties
There is a keto-enol tautomerism in the 1,3-indanedione molecule . A further bromine atom can be introduced into the compound via this enol form, resulting in 2,2-dibromo-1,3-indandione .
If 2-bromo-1,3-indanedione is treated with potassium iodide and hydrochloric acid , the bromine atom is split off, creating elemental iodine and 1,3-indanedione.
The reduction of 2-bromo-1,3-indanedione according to Clemmensen with amalgamated zinc in hydrochloric acid leads to 2-bromoindane . 2-bromoindene is formed as a by -product .
Individual evidence
- ↑ a b c d data sheet 2-Bromo-1,3-indandione, technical, ≥90.0% (AT) from Sigma-Aldrich , accessed on January 27, 2014 ( PDF ).
- ↑ a b c D. Nematollahi, N. Akaberi: "Electrochemical Study of Bromide in the Presence of 1,3-Indandione. Application to the Electrochemical Synthesis of Bromo Derivatives of 1,3-Indandione", in: Molecules , 2001 , 6 , Pp. 639-646 ( full text ).
- ^ SA Galton, M. Kalafer, FM Beringer: "Rearrangements in the Clemmensen reduction of 1-indanones and, 1,3-indandiones", in: J. Org. Chem. , 1970 , 35 (1), pp. 1- 6 ( doi : 10.1021 / jo00826a001 ).