Methyl-2-oxocyclohexancarboxylat

Bezeichnung:Methyl-2-oxocyclohexancarboxylat

CAS-Nr41302-34-5

Englisch Name:Methyl 2-oxocyclohexanecarboxylate

CBNumberCB4458515

SummenformelC8H12O3

Molgewicht156.18

MOL-Datei41302-34-5.mol

Synonyma

Methyl-2-oxocyclohexancarboxylat

Methyl-2-oxocyclohexancarboxylat physikalisch-chemischer Eigenschaften

Siedepunkt	50 °C/0.2 mmHg (lit.)
Dichte	1.10 g/mL at 20 °C (lit.)
Brechungsindex	n20/D 1.483
Flammpunkt	85 °C
storage temp.	Inert atmosphere,Store in freezer, under -20°C
Aggregatzustand	Liquid
pka	12.04±0.20(Predicted)
Farbe	Clear colorless to slightly yellow
BRN	510258
InChI	InChI=1S/C8H12O3/c1-11-8(10)6-4-2-3-5-7(6)9/h6H,2-5H2,1H3
InChIKey	JEENWEAPRWGXSG-UHFFFAOYSA-N
SMILES	C1(C(OC)=O)CCCCC1=O
LogP	0.290 (est)
EPA chemische Informationen	Cyclohexanecarboxylic acid, 2-oxo-, methyl ester (41302-34-5)

Sicherheit

S-Sätze:	23-24/25
RIDADR	NA 1993 / PGIII
WGK Germany	3
HS Code	29183000

Methyl 2-oxocyclohexanecarboxylate Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
clear colorless to slightly yellow liquid
Verwenden
Methyl 2-oxocyclohexanecarboxylate has been used in the synthesis of substituted tetrahydrobenzofuran derivatives via reaction with propargylic esters in the presence of palladium catalyst.
Verwenden
Methyl 2-Oxocyclohexanecarboxylate is a novel intermediate for the preparation of TRPA1 antagonists for treatment of pain and other TRPA1-associated diseases.
Synthesis Reference(s)
Journal of the American Chemical Society, 102, p. 431, 1980 DOI: 10.1021/ja00521a100
Organic Syntheses, Coll. Vol. 7, p. 351, 1990
Synthese
The flask is flushed with nitrogen and charged with 18.02 g (0.20 mol) of dimethyl carbonate, 50 mL of anhydrous tetrahydrofuran, and 6.12 g (0.25 mol) of sodium hydride. The suspension is stirred and heated to reflux temperature, at which time the slow, dropwise addition of 7.80 g (0.080 mol) of cyclohexanone in 20 mL of dry tetrahydrofuran is begun. After 2 min, 0.306 g (0.0076 mol) of powdered potassium hydride is added to initiate the reaction. The addition of cyclohexanone is continued over a 1-hr period. The mixture is stirred and heated at reflux for another 30 min, cooled in an ice bath for 15–20 min, and hydrolyzed by slowly adding 75 mL of 3 M aqueous acetic acid. The flask's contents are poured into 100 mL of aqueous sodium chloride, and the aqueous mixture is extracted with four 150-mL portions of chloroform. The organic layers are combined, dried with anhydrous sodium sulfate, and concentrated at room temperature with a rotary evaporator. Distillation of the residual liquid under reduced pressure gives 9.8–10.8 g (79–87%) of methyl 2-oxocyclohexanecarboxylate as a colorless liquid, bp 53–55°C.

Methyl 2-oxocyclohexanecarboxylate Upstream-Materialien And Downstream Produkte

Methyl-2-oxocyclohexancarboxylat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

41302-34-5, Methyl 2-oxocyclohexanecarboxylate Verwandte Suche:

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