Cyclobutene

Base Information

• Chemical Name: Cyclobutene
• CAS No.: 822-35-5
• Molecular Formula: C4H6
• Molecular Weight: 54.0916
• European Community (EC) Number: 212-496-8
• DSSTox Substance ID: DTXSID60231616
• Nikkaji Number: J1.737J
• Wikipedia: Cyclobutene
• Wikidata: Q411757
• Metabolomics Workbench ID: 57654
• Mol file: 822-35-5.mol

Synonyms:Cyclobutene

Chemical Property of Cyclobutene

Chemical Property:

• Vapor Pressure: 1690mmHg at 25°C
• Refractive Index: 1.473
• Boiling Point: 2 °C at 760 mmHg
• Density: 0.841g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 54.0469501914
• Heavy Atom Count: 4
• Complexity: 29.3

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC=C1

Technology Process of Cyclobutene

There total 49 articles about Cyclobutene 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: 90.0%

cyclobutyl 4-methylbenzenesulfonate (10437-85-1) → cyclobutene (822-35-5)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 70 ℃; for 1.66667h;

DOI:10.1016/S0040-4020(01)88564-1

Reference yield: 21.0%

1,1-dibromocyclobutane (33742-81-3) → dispiro(2.1.3.0)octane (63783-86-8) + 1,2-dimethylspiro(2.3)hex-1-ene (108909-90-6) + cyclobutene (822-35-5) + methylene cyclopropane (6142-73-0)

Guidance literature:

With dimethylacetylene; methyllithium; In diethyl ether; at -35 ℃; Further byproducts given;

DOI:10.1016/S0040-4039(00)85213-2

Reference yield: 11.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + diazocyclobutane (93685-07-5) → cyclobutanone azine (72593-07-8) + 7-Phenyl-5,6-diaza-spiro[3.4]oct-5-ene (93685-08-6) + cyclobutene (822-35-5) + methylene cyclopropane (6142-73-0)

Guidance literature:

at 140 ℃; under 0.0001 Torr;

upstream raw materials:

1,2-trans-dibromocyclobutane

cyclobutyl-dimethyl-amine oxide

cyclobutyl-trimethyl-ammonium; iodide

styrene

Downstream raw materials:

cyclobutane

1,2-dichloro-cyclobutane

buta-1,3-diene

n-butane

Refernces

• 1、 Wildi, Eva A.,Engen, Donna Van,Carpenter, Barry K.. "Thermal Reactions of 2,3-Diazabicyclohex-2-ene. The First Example of a Disrotatory Diazacyclobutene Ring Opening". . p. 7994 - 7996. Retrieved 1980.
• 2、 Demchuk, Oleksandr P.,Hryshchuk, Oleksandr V.,Vashchenko, Bohdan V.,Trofymchuk, Serhii A.,Melnykov, Kostiantyn P.,Skreminskiy, Artem,Volochnyuk, Dmitriy M.,Grygorenko, Oleksandr O.. "Fluoroalkyl-Containing 1,2-Disubstituted Cyclobutanes: Advanced Building Blocks for Medicinal Chemistry". . p. 87 - 95. Retrieved 2021.
• 3、 Hancock, Erin N.,Kuker, Erin L.,Tantillo, Dean J.,Brown, M. Kevin. "Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid". supporting information. p. 436 - 441. Retrieved 2019/11/25.
• 4、 McAlpine, Neil J.,Wang, Long,Carrow, Brad P.. "A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission". supporting information. p. 13634 - 13639. Retrieved 2018/10/24.