Cyclobutanone

Base Information

• Chemical Name: Cyclobutanone
• CAS No.: 1191-95-3
• Deprecated CAS: 2010999-65-0
• Molecular Formula: C4H6O
• Molecular Weight: 70.091
• Hs Code.: 29142900
• European Community (EC) Number: 214-745-6
• NSC Number: 87632
• UNII: 6PF2SH405U
• DSSTox Substance ID: DTXSID9061592
• Nikkaji Number: J80.072D
• Wikipedia: Cyclobutanone
• Wikidata: Q1147434
• Mol file: 1191-95-3.mol

Synonyms:CYCLOBUTANONE;1191-95-3;UNII-6PF2SH405U;6PF2SH405U;EINECS 214-745-6;NSC 87632;NSC-87632;Cyclobutanone, 98+%;AI3-37787;cyclobutyloxy;cyclobutanon;cylcobutanone;cylobutanone;3-cyclobutanone;MFCD00001332;Cyclobutanone, 99%;DTXSID9061592;BCP26050;NSC87632;STR06460;BBL102042;STL555841;AKOS005259133;CS-W001200;PS-9376;SB40655;4-(2,4-DINITROPHENYLAZO)-PHENOL;AM20070575;C1913;FT-0600042;EN300-25701;A804218;Q1147434;W-108526;F0001-0313

Chemical Property of Cyclobutanone

Chemical Property:

• Appearance/Colour: Clear colourless to slightly yellow liquid
• Vapor Pressure: 43.4mmHg at 25°C
• Melting Point: -50.9 °C
• Refractive Index: n20/D 1.421(lit.)
• Boiling Point: 96.5 °C at 760 mmHg
• Flash Point: 10 °C
• PSA: 17.07000
• Density: 1.038 g/cm³
• LogP: 0.73940
• Storage Temp.: 0-6°C
• Water Solubility.: INSOLUBLE
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 70.041864811
• Heavy Atom Count: 5
• Complexity: 50.7

Purity/Quality:

99% ^*data from raw suppliers

Cyclobutanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F+
• Hazard Codes: F,F+
• Statements: 10-11
• Safety Statements: 23-24/25-9-33-29-16-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: C1CC(=O)C1
• 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.
• 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.

Technology Process of Cyclobutanone

There total 89 articles about Cyclobutanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

cyclobutanol (2919-23-5) → cyclobutanone (1191-95-3)

Guidance literature:

With iodosylbenzene; 4 A molecular sieve; sodium ruthenate(VI); In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(00)00531-1

Reference yield: 13.0%

Cyclobutylidencyclooctan (129731-37-9) → 9,10,19,20-tetraoxadispiro[7.2.7.2]eicosane (5681-37-8) + cycloactanone (502-49-8) + cyclobutanone (1191-95-3)

Guidance literature:

With ozone; In pentane; at -10 ℃;

Reference yield: 3.0%

Cyclobutylidencyclooctan (129731-37-9) → 4-butanolide (96-48-0) + cycloactanone (502-49-8) + cyclobutanone (1191-95-3) + 5,14,15-Trioxadispiro<3.1.7.2>pentadecan (129756-48-5)

Guidance literature:

With ozone; In polyethylene; at -75 ℃; for 10h;

upstream raw materials:

diazomethane

Ketene

diethyl ether

ethanol

Downstream raw materials:

4-butanolide

1-hydroxycyclobutane-1-carboxylic acid

2-bromocyclobutanone

cyclobutane

Refernces

• 1、 Weber, Juergen,Haslinger, Ulrike,Brinker, Udo H.. "1-bromobicyclo[1.1.0]butane as an easily obtainable C4-building block: A novel route to cyclobutanone". . p. 6085 - 6086. Retrieved 1999.
• 2、 Sieja. "". . p. 108. Retrieved 1972.
• 3、 Ogura,K. et al.. "-". . p. 3653 - 3656. Retrieved 1974.
• 4、 Hu, Zongmin,Du, Hongxia,Man, Wai-Lun,Leung, Chi-Fai,Liang, Haojun,Lau, Tai-Chu. "Catalytic reactions of chlorite with a polypyridylruthenium(ii) complex: Disproportionation, chlorine dioxide formation and alcohol oxidation". . p. 1102 - 1104. Retrieved 2012.
• 5、 Mucientes,Poblete,Rodriguez,Santiago. "Kinetic study of ruthenium (VI)-catalyzed oxidation of 2-propanol by alkaline hexacyanoferrate (III)". . p. 901 - 908. Retrieved 1999.
• 6、 Kuivila,Becker. "". . p. 5329. Retrieved 1952.
• 7、 Na, Young Oh,Suh, Yumi,Mi, Joo Park,Mi, Sook Seo,Kim, Jinheung,Nam, Wonwoo. "Mechanistic insight into alcohol oxidation by high-valent iron-oxo complexes of heme and nonheme ligands". . p. 4235 - 4239. Retrieved 2005.
• 8、 Rocek,Peng. "-". . p. 7622. Retrieved 1977.
• 9、 Deangelo, Joseph D.,Hatano, Sayaka,Thamattoor, Dasan M.. "Generation and Rearrangement of (1-Hydroxycyclopropyl)- A nd (1-Hydroxycyclobutyl)carbene". . p. 890 - 893. Retrieved 2019.
• 10、 Hanack,M. et al.. "-". . p. 3871 - 3876. Retrieved 1967.