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126-81-8 - Dimedone, 98% - 5,5-Dimethyl-1,3-cyclohexanedione - A10140 - Alfa Aesar

A10140 Dimedone, 98%

CAS Number
126-81-8
Synonyms
5,5-Dimethyl-1,3-cyclohexanedione

Size Price ($) Quantity Availability
25g 22.69
100g 65.92
500g 231.30
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Dimedone, 98%

MDL
MFCD00001588
EINECS
204-804-4

Chemical Properties

Formula
C8H12O2
Formula Weight
140.18
Melting point
146-150°
Solubility
Soluble in methanol, ethanol, benzene and chloroform. Slightly soluble in water.

Applications

Reagent used in synthesis of fused 3-methylfuransDimedone is used in organic chemistry to identify the presence of aldehyde group. It is also used as a catalyst in the formation of transition-metal complexes. Further, it is also employed in colorimetry, crystallography, luminescence and spectrophotometric analysis. In addition to this, it is used in the synthesis of naturally occurring fused 3-methylfurans.

Notes

Light sensitive. Incompatible with oxidizing agents, strong acids and strong bases.

Literature References

Classical reagent for the identification and isolation of aldehydes: J. Org. Chem., 11, 95 (1946).

For conditions leading to exclusive 2-monomethylation, see: Synth. Commun., 3, 347 (1973). For direct nitration at the 2-position, see review on ɑ-nitroketones: Synthesis, 261 (1980).

Undergoes an example of an oxidative addition of 1,3-dicarbonyl compounds, mediated by CAN (Cerium(IV)­ ammonium nitrate, A12882), to give an alkene, e.g. with 2-methyl-2-pentene, the product is a fused dihydrofuran derivative: J. Chem. Soc., Perkin 1, 187 (1995):

A comparative study has shown that CAN is superior to Mn(OAc)3 for this type of reaction: J. Chem. Soc., Perkin 1, 1487 (1996).

Moosavi-Zare, A. R.; Zolfigol, M. A.; Zarei, M.; Zare, A.; Khakyzadeh, V. Application of silica-bonded imidazolium-sulfonic acid chloride (SBISAC) as a heterogeneous nanocatalyst for the domino condensation of arylaldehydes with 2-naphthol and dimedone. J. Mol. Liq. 2015, 211, 373-380.

Khazaei, A.; Gholami, F.; Khakyzadeh, V.; Moosavi-Zare, A. R.; Afsar, J. Magnetic core-shell titanium dioxide nanoparticles as an efficient catalyst for domino Knoevenagel-Michael-cyclocondensation reaction of malononitrile, various aldehydes and dimedone. RSC Adv. 2015, 5 (19), 14305-14310.

Other References

Merck
14,3242
Beilstein
471489
Harmonized Tariff Code
2914.29
TSCA
Yes
RTECS
GV0345000

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