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Cyclobutanone

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.
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CAS:1191-95-3
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Cyclobutanone manufacturers

  • Cyclobutanone
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  • $0.00 / 1kg
  • 2024-02-26
  • CAS:1191-95-3
  • Min. Order: 1kg
  • Purity: 98%
  • Supply Ability: Kgs
  • Cyclobutanone
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  • 2023-11-01
  • CAS:1191-95-3
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  • Purity: 99.0%min
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  • Cyclobutanone
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  • $5.00 / 1KG
  • 2023-05-12
  • CAS:1191-95-3
  • Min. Order: 1KG
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Cyclobutanone Basic information
Description References
Product Name:Cyclobutanone
Synonyms:CBON;CYCLOBUTANONE;Cyclobutanone, 98+%;Cyclobutanone 98%;Cyclobutanone, 98%, stab. with ca 0.01% BHT;Oxocyclobutane;Cyclobutanone (stabilized with Na2CO3);Cyclobutanone, 98%, stabilized
CAS:1191-95-3
MF:C4H6O
MW:70.09
EINECS:214-745-6
Product Categories:Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;C3 to C6;Carbonyl Compounds;Ketones;ketone;Carbonyl Compounds;Pharmaceutical Intermediates;cyclic compounds;bc0001;1191-95-3
Mol File:1191-95-3.mol
Cyclobutanone Structure
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.)
Fp 50 °F
storage temp. 2-8°C
solubility soluble in Dichloromethane
form Liquid
Specific Gravity0.938
color Clear colorless to slightly yellow
Water Solubility INSOLUBLE
BRN 1560289
Stability:Volatile
InChIKeySHQSVMDWKBRBGB-UHFFFAOYSA-N
CAS DataBase Reference1191-95-3(CAS DataBase Reference)
EPA Substance Registry SystemCyclobutanone (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 Yes
HazardClass 3
PackingGroup II
HS Code 29142900
MSDS Information
ProviderLanguage
Cyclobutanone English
SigmaAldrich English
ACROS English
ALFA English
Cyclobutanone Usage And Synthesis
DescriptionCyclobutanone 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 PropertiesClear colourless to slightly yellow liquid
UsesCyclobutanone 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.
PreparationThe 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.
Purification MethodsTreat 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.]
Tag:Cyclobutanone(1191-95-3) Related Product Information
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