94275-22-6

Basic information

• Product Name: 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene
• CAS NO: 94275-22-6
• Molecular Formula: C₁₆H₁₄Br₂
• Molecular Weight: 366.0904
• Mol File: 94275-22-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 388°C at 760 mmHg
• Flash Point: 220.4°C
• Density: 1.589g/cm³
• Vapor Pressure: 7.08E-06mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene(CAS DataBase Reference)
• NIST Chemistry Reference: 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene(94275-22-6)
• EPA Substance Registry System: 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene(94275-22-6)

Safety Data

• Hazardous Substances Data: 94275-22-6(Hazardous Substances Data)

Upstream product

• 1460-59-9 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene 
• 91-13-4 α,α'-dibromo-o-xylene 

Downstream Products

• 53397-65-2 sym-dibenzo-1,5-cyclooctadiene-3,7-diyne 
• 1460-59-9 5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene 
• 2975-71-5 2-[(3-oxo-1,3-dihydro-2-benzofuran-1-yl)methyl]benzoic acid 
• 67761-47-1 (5Z,11Z)-5,11-diphenyldibenzo[a,e][8]annulene 

Relevant articles and documents

Iridium-Triggered Allylcarbamate Uncaging in Living Cells

Designing a metal catalyst that addresses the major issues of solubility, stability, toxicity, cell uptake, and reactivity within complex biological milieu for bioorthogonal controlled transformation reactions is a highly formidable challenge. Herein, we report an organoiridium complex that is nontoxic and capable of the uncaging of allyloxycarbonyl-protected amines under biologically relevant conditions and within living cells. The potential applications of this uncaging chemistry have been demonstrated by the generation of diagnostic and therapeutic agents upon the activation of profluorophore and prodrug in a controlled fashion within HeLa cells, providing a valuable tool for numerous potential biological and therapeutic applications.

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.

An efficient synthesis of dibenzocycloocta-4a,6a,-diene-5,11-diyne and its precursors

Two efficient syntheses of dibenzocyclooctadienediyne 1 were developed employing known reactions, which utilize commercially available reagents. Both methods are an improvement on known syntheses resulting in 41% and 43% overall yields. The latter method also offers an efficient synthesis of dibenzocyclooctatetraene 9, which is one of the key reagents now commercially unavailable.