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346578

Sigma-Aldrich

5-Phenyl-1,3-cyclohexanedione

96%

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About This Item

Linear Formula:
C6H5C6H7(=O)2
CAS Number:
493-72-1
Molecular Weight:
188.22
MDL number:
MFCD00051846
UNSPSC Code:
12352100
PubChem Substance ID:
24861418
NACRES:
NA.22

Assay

96%

mp

188 °C (lit.)

SMILES string

O=C1CC(CC(=O)C1)c2ccccc2

InChI

1S/C12H12O2/c13-11-6-10(7-12(14)8-11)9-4-2-1-3-5-9/h1-5,10H,6-8H2

InChI key

UPPYKNLSSLIIAZ-UHFFFAOYSA-N

General description

5-Phenyl-1,3-cyclohexanedione is a 1,3-diketone. Reaction of 5-phenyl-1,3-cyclohexanedione with N-substituted isatins in pyrindine has been investigated.

Application

5-Phenyl-1,3-cyclohexanedione may be used:
  • in the synthesis of hexahydrobenzo[a]phenanthridin-4-one derivatives via condensation with N-arylmethylene-2-naphthylamines
  • in the preparation of benzophenanthridine derivatives
  • in the preparation of iodonium betaine
  • in the synthesis of various 2H-pyrans by iodine-catalyzed reactions

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reactions of bisazomethines of the naphtalene series with 1, 3-diketones.
Kozlov SN, et al.
Russ. J. Gen. Chem., 73(9), 1424-1440 (2009)
Chunhui Dai et al.
Beilstein journal of organic chemistry, 8, 986-993 (2012-09-29)
A mild and practical synthesis of spirooxindole [1,3]oxazino derivatives from N-substituted isatins and 1,3-dicarbonyl compounds with pyridine derivatives is reported. The reactions provided good to excellent yields. Further exploration of the molecular diversity of these compounds is demonstrated through Diels-Alder
Efforts toward the synthesis of liphatic iodonium salts.
Dence JB and Roberts JD.
The Journal of Organic Chemistry, 33(3), 1251-1253 (1968)
Synthesis of Benzo [a] phenanthridine Derivatives by Condensation of N-Arylmethylene-2-naphthylamines with 5-Phenyl-and 5-(p-Methoxyphenyl)-1, 3-cyclohexanediones.
Kozlov NG, et al.
Russ. J. Gen. Chem., 72(8), 1238-1242 (2002)
Iodine-Catalyzed One-Pot Synthesis of 2H-Pyrans by Domino Knoevenagel/6p-Electrocylization.
Jung EJ, et al.
Bull. Korean Chem. Soc., 30, 2833-2836 (2009)

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