| Identification | More | [Name]
Cyclobutanone | [CAS]
1191-95-3 | [Synonyms]
CBON
CYCLOBUTANONE
Cyclobutanone, 98+%
Cyclobutanone 98%
Cyclobutanone, 98%, stab. with ca 0.01% BHT | [EINECS(EC#)]
214-745-6 | [Molecular Formula]
C4H6O | [MDL Number]
MFCD00001332 | [Molecular Weight]
70.09 | [MOL File]
1191-95-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colourless to slightly yellow liquid | [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.)
| [Fp ]
50 °F
| [storage temp. ]
0-6°C | [solubility ]
soluble in Dichloromethane | [form ]
Liquid | [color ]
Clear colorless to slightly yellow | [Specific Gravity]
0.938 | [Water Solubility ]
INSOLUBLE | [BRN ]
1560289 | [Stability:]
Volatile | [InChIKey]
SHQSVMDWKBRBGB-UHFFFAOYSA-N | [CAS DataBase Reference]
1191-95-3(CAS DataBase Reference) | [EPA Substance Registry System]
1191-95-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,F+ | [Risk Statements ]
R10:Flammable.
R11:Highly Flammable. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S9:Keep container in a well-ventilated place .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S16:Keep away from sources of ignition-No smoking .
S7/9:Keep container tightly closed and in a well-ventilated place . | [RIDADR ]
UN 1224 3/PG 3
| [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29142900 |
| Questions And Answer | Back Directory | [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 |
| Hazard Information | Back Directory | [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.] |
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