Cyclobutanone Chemical Properties

Melting point:

-50.9 °C

Boiling point:

99 °C (lit.)

Density 

0.938 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.421(lit.)

Flash point:

50 °F

storage temp. 

2-8°C

solubility 

soluble in Dichloromethane

form 

Liquid

Specific Gravity

0.938

color 

Clear colorless to slightly yellow

Water Solubility 

INSOLUBLE

BRN 

1560289

Stability:

Volatile

InChIKey

SHQSVMDWKBRBGB-UHFFFAOYSA-N

CAS DataBase Reference

1191-95-3(CAS DataBase Reference)

EPA Substance Registry System

Cyclobutanone (1191-95-3)

Safety Information

Hazard Codes 

F,F+

Risk Statements 

10-11

Safety Statements 

23-24/25-9-33-29-16-7/9

RIDADR 

UN 1224 3/PG 3

WGK Germany 

3

TSCA 

TSCA listed

HazardClass 

3

PackingGroup 

II

HS Code 

29142900

MSDS

• Language:English Provider:Cyclobutanone
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Cyclobutanone Usage And Synthesis

Description

Cyclobutanone is an organic compound with a four-membered cyclic ketone. It is used in preparation of cyclobutane derivatives, as a starting material for aminocyclobutanecarboxylic acid through sulfonyloxiranes, to prepare dihydro-furan-2-one in presence of polystyrene-bound phenylselenic acid as catalyst. It is also involved in the photochemical synthesis of nucleoside analogues such as bicyclic nucleosides and isonucleosides. Furthermore, it is used to synthesis fatty acid, 2-oxo-cyclobutane undecanoic acid, which is used in the development of an enzyme-linked immunosorbent assy for the detection of irradiated foods.

References

[1] https://en.wikipedia.org/wiki/Cyclobutanone
[2] https://www.alfa.com/de/catalog/A13068/
[3] https://www.scbt.com/scbt/de/product/2-oxo-cyclobutane-undecanoic-acid-169263-77-8/;jsessionid=Ay2KMCxORq9y-EC6YoYnGGtCnymUGxQi5Lpd-YuCZoW22Re8Xf4w!-2072765631

Chemical Properties

Clear colourless to slightly yellow liquid

Uses

Cyclobutanone is used in preparation of cyclobutane derivatives. It is used as a starting material for aminocyclobutanecarboxylic acid through sulfonyloxiranes. It is also used to prepare dihydro-furan-2-one in presence of polystyrene-bound phenylselenic acid as catalyst. Further, it is involved in the photochemical synthesis of nucleoside analogues such as bicyclic nucleosides and isonucleosides.

Preparation

The Russian chemist Nikolai Kischner first prepared cyclobutanone in 1905. He synthesized cyclobutanone in a low yield from cyclobutanecarboxylic acid in several reaction steps.
Another synthesis of cyclobutanone involves lithium-catalyzed rearrangement of oxaspiropentane, which is formed by epoxidation of the easily accessible methylenecyclopropane.

Synthesis

In a 2-L, three-necked, round-bottomed flask equipped with a reflux condenser are placed 250 mL of water, 48 mL (ca. 0.55 mol) of concentrated hydrochloric acid, and 49.5 g (0.65 mol) of cyclopropylcarbinol; the reaction mixture is refluxed for ca. 100 min. The flask is then immersed in an ice bath equipped with a mechanical stirrer, a thermometer, and a dropping funnel (using a three-way adapter, parallel sidearm), and the reflux condenser is replaced by an ethanol–dry ice trap connected to a U-tube immersed in an ethanol–dry ice bath to ensure condensation of the very volatile cyclobutanone. The flask is charged with an additional 48 mL (ca. 0.55 mol) of concentrated hydrochloric acid in 200 mL of water and 440 g (3.5 mol) of oxalic acid dihydrate. The heterogeneous mixture is stirred for ca. 15 min to saturate the solution with oxalic acid. A solution of 162 g (1.62 mol) of chromium trioxide in 250 mL of water is added dropwise with stirring at such a rate that the temperature of the reaction mixture is kept between 10°C and 15°C (NaCl–ice bath, −5°C to −10°C) and the generation of carbon dioxide remains gentle. After the oxidation is completed, the ice bath is removed and stirring is continued for ca. 1 hr to bring the reaction mixture to room temperature.
The reaction mixture is poured into a 2-L separatory funnel and extracted with four 200-mL portions of methylene chloride. The extracts (the lower phase) are combined, dried over anhydrous magnesium sulfate containing a small amount of anhydrous potassium carbonate (to remove traces of hydrochloric acid), and filtered, and the filtrate is concentrated by distillation through a vacuum-insulated silvered column packed with glass helices and equipped with an adjustable stillhead, until the pot temperature rises to 80°C. The crude product is then transferred to a 100-mL flask and distilled through the same column (reflux ratio 10:1) to give 14–16 g (0.20–0.23 mol), 31–35% overall yield (based on pure cyclopropyl carbinol) of cyclobutanone.

Purification Methods

Treat cyclobutanone with dilute aqueous KMnO4, dry it with molecular sieves and fractionally distil it. Purify it via the semicarbazone, then regenerate the ketone, dry it (CaSO4), and distil it in a stainless steel spinning-band (or Vigreux, p 11) column. Alternatively, purify it by preparative gas chromatography using a Carbowax 20-M column at 80o. (This treatment also removes acetone). The oxime has m 84-85o (from pet ether) and the semicarbazone has m 212-212-5o (220-221o from MeOH or H2O, Buchanan et al. J Am Chem Soc 64 2701 1942). [Salaun Org Synth 57 36 1977, Fitzer & Quabeck Synthesis 299 1987, Beilstein 7 IV 3.]

Cyclobutanone(1191-95-3)Related Product Information

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