35825-94-6

Basic information

• Product Name: tetracyclo[3.2.0.0~2,7~.0~4,6~]hept-3-yl acetate
• CAS NO: 35825-94-6
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• Mol File: 35825-94-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 218.3°C at 760 mmHg
• Flash Point: 73.6°C
• Density: 1.36g/cm³
• Vapor Pressure: 0.127mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: tetracyclo[3.2.0.0~2,7~.0~4,6~]hept-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: tetracyclo[3.2.0.0~2,7~.0~4,6~]hept-3-yl acetate(35825-94-6)
• EPA Substance Registry System: tetracyclo[3.2.0.0~2,7~.0~4,6~]hept-3-yl acetate(35825-94-6)

Safety Data

• Hazardous Substances Data: 35825-94-6(Hazardous Substances Data)

Upstream product

• 4796-68-3 2,5-norbornadien-7-yl benzoate 
• 13426-49-8 7-Acetoxynorbornadien 
• 877-06-5 7-tert-butoxynorbornadiene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 13426-49-8 7-acetoxynorbornadiene 

Downstream Products

• 1342805-75-7 p-nitrophenyl carbonate quadricyclane 
• 1342805-67-7 Ni(C₆H₅CSC₆H₅CS)2(C₇H₇OCOCH₃) 
• 531-45-3 heptafulvalene 
• 64-19-7 acetic acid 
• 71-43-2 benzene 

Relevant articles and documents

Photodissociation Dynamics of Cyclopropenylidene, c-C3H2

In this joint experimental and theoretical study we characterize the complete dynamical "life cycle" associated with the photoexcitation of the singlet carbene cyclopropenylidene to the lowest lying optically bright excited electronic state: from the initial creation of an excited-state wavepacket to the ultimate fragmentation of the molecule on the vibrationally hot ground electronic state. Cyclopropenylidene is prepared in this work using an improved synthetic pathway for the preparation of the precursor quadricyclane, thereby greatly simplifying the assignment of the molecular origin of the measured photofragments. The excitation process and subsequent non-adiabatic dynamics have been previously investigated employing time-resolved photoelectron spectroscopy and are now complemented with high-level ab initio trajectory simulations that elucidate the specific vibronic relaxation pathways. Lastly, the fragmentation channels accessed by the molecule following internal conversion are probed using velocity map imaging (VMI) so that the identity of the fragmentation products and their corresponding energy distributions can be definitively assigned.

A bioorthogonal quadricyclane ligation

New additions to the bioorthogonal chemistry compendium can advance biological research by enabling multiplexed analysis of biomolecules in complex systems. Here we introduce the quadricyclane ligation, a new bioorthogonal reaction between the highly strained hydrocarbon quadricyclane and Ni bis(dithiolene) reagents. This reaction has a second-order rate constant of 0.25 M-1 s-1, on par with fast bioorthogonal reactions of azides, and proceeds readily in aqueous environments. Ni bis(dithiolene) probes selectively labeled quadricyclane-modified bovine serum albumin, even in the presence of cell lysate. We have demonstrated that the quadricyclane ligation is compatible with, and orthogonal to, strain-promoted azide-alkyne cycloaddition and oxime ligation chemistries by performing all three reactions in one pot on differentially functionalized protein substrates. The quadricyclane ligation joins a small but growing list of tools for the selective covalent modification of biomolecules.

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Tetrachloro-o-benzoquinone (1) reacts as heterodiene with 7-acetoxyquadricyclane (3) to give 4 and 5 and as electron deficient monocarbonyl compound to give 6. 1:2-adducts (8, 9) were also isolated, which presumably result from a primarily formed homodiene adduct (13) through a consecutive reaction with 3. The structures of 8 and9 have been identified by X-ray analysis.