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HomeProduct name list1,2-Cyclohexanedione

1,2-Cyclohexanedione

  • CAS NO.:765-87-7
  • Empirical Formula: C6H8O2
  • Molecular Weight: 112.13
  • MDL number: MFCD00001648
  • EINECS: 212-155-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-25 18:01:18
1,2-Cyclohexanedione Structural

What is 1,2-Cyclohexanedione?

Chemical properties

clear yellow liquid after melting

The Uses of 1,2-Cyclohexanedione

1,2-Cyclohexanedione have been used as a substrate to study enzyme cyclohexane-1,2-dione hydrolase as a new tool to degrade alicyclic compounds.

The Uses of 1,2-Cyclohexanedione

1,2-Cyclohexanedione is utilized as a substrate to study enzyme cyclohexane-1,2-dione hydrolase, which is a new tool to degrade alicyclic compounds. It also acts as a specific reagent for arginine residues.

Definition

ChEBI: Cyclohexane-1,2-dione is a cyclohexanedione carrying oxo substituents at positions 1 and 2.

Reactions

1,2-Cyclohexanedione may effectively occupy vacant coordination sites and thus promote the present cycloisomerization[1]. Tanaka et al. research the catalytic cycloisomerization of 1,6- and 1,7-diynes leading to trienes and vinylpyrroles by using a cationic rhodium(I)/Segphos complex (2.5-10 mol %) and 1,2-cyclohexanedione (100 mol %). 1,2-Cyclohexanedione

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4658, 1951 DOI: 10.1021/ja01154a048
Tetrahedron Letters, 25, p. 603, 1984 DOI: 10.1016/S0040-4039(00)99949-0
The Journal of Organic Chemistry, 39, p. 3295, 1974 DOI: 10.1021/jo00936a034

References

[1] Ken Tanaka, Masao Hirano, Yousuke Otake. “Cationic Rhodium(I)/Segphos-Catalyzed Cycloisomerization of 1,6- and 1,7-Diynes in the Presence of 1,2-Cyclohexanedione.” Organic Letters 9 20 (2007): 3953–3956.

Properties of 1,2-Cyclohexanedione

Melting point: 34-38 °C (lit.)
Boiling point: 193-195 °C (lit.)
Density  1,118 g/cm3
refractive index  1.518-1.52
FEMA  3458 | 2-HYDROXY-2-CYCLOHEXEN-1-ONE
Flash point: 184 °F
storage temp.  2-8°C
solubility  Soluble in DMSO
form  Liquid After Melting
color  Clear yellow
Odor at 10.00 % in dipropylene glycol. sweet acorn nut skin maple caramel brothy
Water Solubility  Soluble
JECFA Number 424
BRN  507419
CAS DataBase Reference 765-87-7(CAS DataBase Reference)
NIST Chemistry Reference c-hexane-1,2-dione(765-87-7)
EPA Substance Registry System 1,2-Cyclohexanedione (765-87-7)

Safety information for 1,2-Cyclohexanedione

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 1,2-Cyclohexanedione

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