1,3-Cyclohexanedione Chemical Properties

Melting point:

101-105 °C (lit.)

Boiling point:

170.05°C (rough estimate)

Density 

1,1 g/cm³

vapor pressure 

0.018Pa at 25℃

refractive index 

1.4576 (estimate)

storage temp. 

Store at +2°C to +8°C.

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Powder

pka

5.26(at 25℃)

color 

Pale yellow to beige

Water Solubility 

soluble

Merck 

14,3178

BRN 

385888

LogP

0.461 at 21.4℃ and pH3.2

Surface tension

69.9mN/m at 1.01g/L and 22℃

CAS DataBase Reference

504-02-9(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Cyclohexanedione(504-02-9)

EPA Substance Registry System

1,3-Cyclohexanedione (504-02-9)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

GV0350000

F 

8-21

TSCA 

Yes

HS Code 

29142900

MSDS

• Language:English Provider:Dihydroresorcinol
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,3-Cyclohexanedione Usage And Synthesis

Chemical Properties

pale yellow to beige powder

Uses

1,3-Cyclohexanedione is used in organic synthesis and pharmaceutical intermediates. It is the intermediate of herbicides sulcotrione and nitrosulfonone. It is also nitisinone intermediate.

Uses

1,3-Cyclohexanedione can be used as a building block in the synthesis of:

• 9-substituted 1,8-dioxo-xanthenes by reacting with unactivated aldehydes via aldol condensation/ Michael addition reaction.
• [(1,2,3-triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives by treating with phthalhydrazide, aromatic propargyloxy aldehydes, and azides via a four-component condensation reaction.

It can be also used to prepare 2-substituted adducts, which are important intermediates for the synthesis of ?-enaminones , polyhydroquinoline derivatives , 1,8-dioxo-dodecahydroxanthenes , spirocyclopentanols , oxathioles , and triquinanes.

Definition

ChEBI: 1,3-Cyclohexanedione is a cyclohexanedione carrying oxo substituents at positions 1 and 3. It is a beta-diketone and a cyclohexanedione.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 3206, 1965 DOI: 10.1021/jo01020a506

Purification Methods

Crystallise the dione from *benzene. Dissolve ~50g of the diol in 140mL of *C6H6 under N2, cool, collect the solid and dry it in a vacuum desiccator overnight. It is unstable and should be stored under N2 or Ar at ~0o. [Thompson Org Synth Coll Vol III 278 1955, Beilstein 7 IV 1985.]

1,3-Cyclohexanedione(504-02-9)Related Product Information

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