277-10-1

Basic information

• Product Name: cubane
• Synonyms: cubane;Pentacyclo[4.2.0.02,5.03,8.04,7]octane;Quadriprismane
• CAS NO: 277-10-1
• Molecular Formula: C₈H₈
• Molecular Weight: 104.15
• Mol File: 277-10-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 130-131° (sealed capillary)
• Boiling Point: 130.31°C (rough estimate)
• Appearance: solid
• Density: 0.9155 (estimate)
• Refractive Index: 1.4770 (estimate)
• Stability: Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: cubane(CAS DataBase Reference)
• NIST Chemistry Reference: cubane(277-10-1)
• EPA Substance Registry System: cubane(277-10-1)

Safety Data

• Hazardous Substances Data: 277-10-1(Hazardous Substances Data)

Usage

Description

Cubane is a crystalline hydrocarbon with the chemical formula C8H8, characterized by its unique structure with eight carbon atoms at the corners of a cube, each attached to a hydrogen atom. It was first synthesized in 1964 by Philip Eaton and is known for its highly strained C–C–C bond angle of 90°. Due to its properties, cubane and its derivatives have been investigated for their potential use as high-energy fuels and explosives.

Uses

Used in High-Energy Fuels:
Cubane is used as a high-energy fuel for its potential to provide a significant amount of energy due to its strained molecular structure and high carbon content.
Used in Explosives:
Cubane is used as a component in the development of high-energy explosives, particularly in the form of octanitrocubane, where the hydrogen atoms are replaced by -NO2 groups. Octanitrocubane is considered one of the most powerful chemical explosives known, although only small amounts have been synthesized.
Used in Chemical Research:
Cubane is used as a subject of study in chemical research to better understand its properties, reactivity, and potential applications in various fields, including materials science and energy production.
Used in the Production of Octanitrocubane:
Cubane serves as a starting material for the synthesis of octanitrocubane, a highly powerful explosive with potential applications in military and industrial settings.

Upstream product

• 32846-66-5 cubane-1,4-dicarboxylic acid 
• 29412-62-2 cubane-1,4-dicarboxylic acid dimethyl ester 
• 109-72-8 n-butyllithium 
• 60462-24-0 1,4-cubanedicarboxylic acid dichloride 
• 60462-25-1 Cuban-1,4-dicarbonsaeure-di-tert-butylperester 

Downstream Products

• 629-20-9 1,3,5,7-cyclooctatetraene 
• 20380-30-7 syn-tricyclo{4.2.0.0(2.5)}octa-3,7-diene 
• 59346-69-9 bromocubane 
• 3104-90-3 secocubane 
• 74725-77-2 Iodocubane 
• 280-33-1 bicyclo<2.2.2>octane 
• 3104-91-4 nortwistbrendane 
• 100-42-5 styrene 
• 61771-84-4 1,4-dihydropentalene 
• 33284-11-6 1,5-dihydropentalene 
• 74-86-2 acetylene 
• 71-43-2 benzene 

Relevant articles and documents

Cubene (1,2-Dehydrocubane)

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Synthesis, High-Resolution Infrared Spectroscopy, and Vibrational Structure of Cubane, C8H8

Carbon-cage molecules have generated a considerable interest from both experimental and theoretical points of view. We recently performed a high-resolution study of adamantane (C10H16), the smallest hydrocarbon cage belonging to the diamandoid family (Pirali, O.; et al. J. Chem. Phys. 2012, 136, 024310). There exist another family of hydrocarbon cages with additional interesting chemical properties: the so-called platonic hydrocarbons that comprise dodecahedrane (C20H20) and cubane (C8H8). Both possess C-C bond angles that deviate from the tetrahedral angle (109.8°) of the sp3 hybridized form of carbon. This generates a considerable strain in the molecule. We report a new wide-range high-resolution study of the infrared spectrum of cubane. The sample was synthesized in Bari upon decarboxylation of 1,4-cubanedicarboxylic acid thanks to the improved synthesis of literature. Several spectra have been recorded at the AILES beamline of the SOLEIL synchrotron facility. They cover the 600-3200 cm-1 region. Besides the three infrared-active fundamentals (ν10, ν11, and ν12), we could record many combination bands, all of them displaying a well-resolved octahedral rotational structure. We present here a preliminary analysis of some of the recorded bands, performed thanks the SPVIEW and XTDS software, based on the tensorial formalism developed in the Dijon group. A comparison with ab initio calculations, allowing to identify some combination bands, is also presented.

Nitration of organolithiums and Grignards with dinitrogen tetroxide: Success at melting interfaces

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