1,4-Cyclohexanedione Chemical Properties

Melting point:

77-78.5 °C (lit.)

Boiling point:

112 °C (19.5026 mmHg)

Density 

1.0861

refractive index 

1.4570 (estimate)

Flash point:

132 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol and ethanol.

form 

Crystalline Powder or Flakes

color 

Light yellow to yellow or beige

BRN 

774152

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

LogP

-0.910 (est)

CAS DataBase Reference

637-88-7(CAS DataBase Reference)

NIST Chemistry Reference

1,4-Cyclohexanedione(637-88-7)

EPA Substance Registry System

1,4-Cyclohexanedione (637-88-7)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

F 

8

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29142900

MSDS

• Language:English Provider:1,4-Cyclohexanedione
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,4-Cyclohexanedione Usage And Synthesis

Chemical Properties

tan or yellow crystalline powder

Uses

1,4-Cyclohexanedione is used in the preparation of 1,4 benzoquinone and bromoorganics. It is also used to study the influence of visible light on the bromate-1,4-cyclohexanedione-ferroin oscillating reaction. It plays a vital role in pharmaceuticals, plant growth regulator and as a conducting material.

Definition

ChEBI: 1,4-Cyclohexanedione is a cyclohexanedione with oxo substituents at positions 1 and 4.

Preparation

Synthesis of 1,4-cyclohexanedione: put diethyl succinylsuccinate into a flask, add a mixture of concentrated sulfuric acid, water and ethanol, reflux in oil solution for 5 days, cool, and neutralize to pH with ammonia water = 8; then extract 4 times with chloroform, and recover the chloroform to obtain the crude product; then the crude product is subjected to vacuum distillation, and the distillate is poured into cold petroleum ether, filtered, and air-dried to obtain 1,4-cyclohexanedi Ketone Products.

Synthesis Reference(s)

Synthesis, p. 165, 1981 DOI: 10.1055/s-1981-29377

General Description

1,4-Cyclohexanedione(CHD) undergoes uncatalyzed oscillatory reactions during oxidation by acidic bromate in nitric acid and sulphuric acid solution. It reacts with acidic bromate to form 1,4-dihydroxybenzene which on further oxidation and bromination yields 1,4-benzoquinone and bromoorganics.

Pharmacology

The cyclohexanedione (CHD) herbicides inhibit fatty acid synthesis in plants by interfering with the activity of the enzyme Acetyl-Coenzyme A Carboxylase (ACCase). ACCase-inhibiting herbicides provide excellent control of grass weeds in dicotyledonous and some grass crops. A less-sensitive ACCase mediates the intrinsic resistance of dicotyledonous plants to the AOPP and CHD herbicides (34,35). Although grasses are target species of this group of herbicides, not all are equally affected, and sensitivity differences can occur between varieties or even within a genus.

1,4-Cyclohexanedione (637-88-7)Related Product Information

• Cyclohexane
• 2,5-Hexanedione
• 1,3-Cyclohexanedione
• 2,5-dioxo-1,4-cyclohexanedicarboxylic acid dimethyl ester
• Diethyl succinosuccinate
• DIETHYL 2,5-DIOXOBICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLATE
• 1,2-Cyclohexanedione
• 5-(2-ETHYLTHIO PROPYL)-1,3-CYCLOHEXANEDIONE
• 5-PHENYLCYCLOHEXANE-1,3-DIONE
• 4,4-DIMETHYL-1,3-CYCLOHEXANEDIONE
• Sulcotrione
• 1,4-Cyclohexanedione bis(ethylene ketal)
• 5-ISOPROPYL-1,3-CYCLOHEXANEDIONE
• 2-Methyl-1,3-cyclohexanedione
• FEMA 3269
• 1,4-Cyclohexanedione mono(2,2-dimethyltrimethylene ketal)
• Dimedone
• CYCLOPENTADIENE-QUINONE (2:1)ADDUCT