Cyclohexan-1,3-dion

Bezeichnung:Cyclohexan-1,3-dion

CAS-Nr504-02-9

Englisch Name:1,3-Cyclohexanedione

CBNumberCB8319650

SummenformelC6H8O2

Molgewicht112.13

MOL-Datei504-02-9.mol

Synonyma

Cyclohexan-1,3-dion

Cyclohexan-1,3-dion physikalisch-chemischer Eigenschaften

Schmelzpunkt	101-105 °C (lit.)
Siedepunkt	170.05°C (rough estimate)
Dichte	1,1 g/cm³
Dampfdruck	0.018Pa at 25℃
Brechungsindex	1.4576 (estimate)
storage temp.	Store at +2°C to +8°C.
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
pka	5.26(at 25℃)
Aggregatzustand	Powder
Farbe	Pale yellow to beige
Wasserlöslichkeit	soluble
Merck	14,3178
BRN	385888
InChI	1S/C6H8O2/c7-5-2-1-3-6(8)4-5/h1-4H2
InChIKey	HJSLFCCWAKVHIW-UHFFFAOYSA-N
SMILES	O=C1CCCC(=O)C1
LogP	0.461 at 21.4℃ and pH3.2
Oberflächenspannung	69.9mN/m at 1.01g/L and 22℃
CAS Datenbank	504-02-9(CAS DataBase Reference)
NIST chemische Informationen	1,3-Cyclohexanedione(504-02-9)
EPA chemische Informationen	1,3-Cyclohexanedione (504-02-9)

Sicherheit

S-Sätze:	24/25
WGK Germany	3
RTECS-Nr.	GV0350000
F	8-21
TSCA	TSCA listed
HS Code	29142900
Speicherklasse	13 - Non Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Aquatic Chronic 3 Eye Dam. 1

Gefahreninformationscode (GHS)

1,3-Cyclohexanedione Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
pale yellow to beige powder
Verwenden
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.
Verwenden
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
Synthese
1,3-cyclohexanedione is made by combining resorcinol with sodium formate in water using 5% palladium on carbon in water at a pH of 5-11. After the completion of the reaction, the catalyst is separated by filtration. Next, a sufficient amount of concentrated HCl is added to lower the pH of the mixture to about 3, and the reaction is cooled and stirred for an additional 0.5-4.0 hours. Optionally, sodium chloride may be added to facilitate recovery of 1,3-cyclohexanedione.
läuterung methode
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 Upstream-Materialien And Downstream Produkte

Cyclohexan-1,3-dion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

504-02-9, 1,3-Cyclohexanedione Verwandte Suche:

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