822-35-5

Basic information

• Product Name: cyclobutene
• Synonyms: Cyclobutene
• CAS NO: 822-35-5
• Molecular Formula: C₄H₆
• Molecular Weight: 54.0904
• EINECS: 212-496-8
• Mol File: 822-35-5.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 2°C at 760 mmHg
• Density: 0.841g/cm³
• Vapor Pressure: 1690mmHg at 25°C
• Refractive Index: 1.473
• CAS DataBase Reference: cyclobutene(CAS DataBase Reference)
• NIST Chemistry Reference: cyclobutene(822-35-5)
• EPA Substance Registry System: cyclobutene(822-35-5)

Safety Data

• Hazardous Substances Data: 822-35-5(Hazardous Substances Data)

Usage

General Description

Cyclobutene is a cyclic hydrocarbon with the molecular formula C4H6. It is a flammable gas at room temperature and is highly reactive due to its strained four-membered ring structure. Cyclobutene is commonly used as a building block in organic synthesis and is a key intermediate in the production of various chemical compounds such as pharmaceuticals and polymers. It can undergo polymerization to form cyclobutene-based polymers, which have potential applications in advanced materials and coatings. Due to its instability and reactivity, cyclobutene requires careful handling and storage to prevent unintentional reactions and hazards.

Upstream product

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Downstream Products

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• 144773-93-3 1,5-dibromocyclopentene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 64141-42-0 dispirohexane-3',1''-cyclopropane> 
• 127280-56-2 5,8-Dihydro-8-oxo-7-phenyl-4H-oxocin-2-carbonsaeure-methylester 
• 127280-57-3 4-Oxo-5-phenyl-3-oxatricyclo<4.2.0.0^2,5>octan-2-carbonsaeure-methylester 

Relevant articles and documents

Microwave Spectroscopy of Isotopic Cyclobutene Ozonide as a Means of Quantification of Ozone Isotopomers

The microwave spectrum of cyclobutene ozonide, a new isotopomeric species, has been assigned and the absolute direction of the dipole moment has been determined. The aim of this investigation has been to determine symmetric/asymmetric isotopomer concentrations in an arbitrary 18O-substituted ozone isotopomer mixture. The method we have used consists of transforming the ozone into cyclobutene ozonide and using intensities of rotational lines of these to quantify the composition of the original ozone isotopomer mixture. Such a method has been accomplished; unfortunately propagation of errors renders it difficult to obtain results of high accuracy.

THE MICROWAVE SPECTRUM, STRUCTURE AND DIPOLE MOMENT OF CYCLOBUTENE OZONIDE (2,3,7-TRIOXABICYCLOHEPTANE)

cyclobutene ozonide containing deuterium, 13C and 18O enrichment was prepared by ozonolysis of cyclobutene and via singlet molecular oxygen addition to furan.It was established that the ozonide has Cs symmetry.The structure was determined from the assignment of the microwave spectra of eight isotopic species.The peroxy bond distance of 1.492(5) Angstroem is increased by about 0.03 Angstroem compared with less strained monocyclic ozonides.The ring strain is also evident in several other bond distances and angles when compared with cyclopentene ozonide.The dipole moment is 2.857(2) debye.

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The cyclopropylcarbinyl route to γ-silyl carbocations

The mesylate derivative of cis-1-hydroxymethyl-2-trimethylsilylcyclopropane has been prepared, along with a number of related mesylates and triflates with substituents on the 1-position. These substrates all solvolyze in CD3CO2D to give products derived from cyclopropylcarbinyl cations that undergo further rearrangement to give 3-trimethylsilylcyclobutyl cations. These 3-trimethylsilylcyclobutyl cations are stabilized by a long-range rear lobe interaction with the γ-trimethylsilyl group. When the substituent is electron-withdrawing (CF3, CN, or CO2CH3), significant amounts of bicyclobutane products are formed. The bicyclobutanes are a result of γ-trimethylsilyl elimination from the cationic intermediate that has an unusually long calculated Si-C bond. The solvolysis chemistry of mesylate and triflate derivatives of trans-1-hydroxymethyl-2-trimethylsilylcyclopropane and 1-substituted analogs can be quite different since these substrates do not generally lead to 3-trimethylsilylcyclobutyl cations.

Formal (4+1) cycloaddition of methylenecyclopropanes with 7-aryl-1,3,5-cycloheptatrienes by triple gold(I) catalysis

7-Aryl-1,3,5-cycloheptatrienes react intermolecularly with methylenecyclopropanes in a triple gold(I)-catalyzed reaction to form cyclopentenes. The same formal (4+1) cycloaddition occurs with cyclobutenes. Other precursors of gold(I) carbenes can also be used as the C1 component of the cycloaddition.