205-12-9

Basic information

• Product Name: BENZO(C)FLUORENE
• Synonyms: 3,4-benzofluorene;7H-BENZO[C]FLUORENE;BENZO(C)FLUORENE;benzo(c)fluorene;BENZO[C]FLUORINE;7H-benzo[c]fluorine;NSC 89264
• CAS NO: 205-12-9
• Molecular Formula: C₁₇H₁₂
• Molecular Weight: 216.28
• EINECS: 205-908-2
• Mol File: 205-12-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 125-127℃
• Boiling Point: 398℃
• Flash Point: 185℃
• Appearance: /
• Density: 1.185
• Vapor Pressure: 3.43E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• Stability: Light Sensitive
• CAS DataBase Reference: BENZO(C)FLUORENE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO(C)FLUORENE(205-12-9)
• EPA Substance Registry System: BENZO(C)FLUORENE(205-12-9)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 205-12-9(Hazardous Substances Data)

Usage

Chemical Properties

Plates from ethanol.

Uses

7H-Benzo[c]fluorene is a polycyclic aomatic hydrocarbon (PAH) with mutagenic activity. 7H-Benzo[c]fluorene is a major DNA adduct-forming component of coal tar. Recent studies suggest that 7H-Benzo[c]f luorene may be capable of inducing lung tumors.

Safety Profile

Questionable carcinogen. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Carcinogenicity

Benzo[c]fluorene gave negative results in repeated application and two-stage skin carcinogenesis tests but positive results by oral and interperitoneal administration in mice.

InChI:InChI=1/C17H12/c1-3-7-15-12(5-1)9-10-14-11-13-6-2-4-8-16(13)17(14)15/h1-10H,11H2

Upstream product

• 56-23-5 tetrachloromethane 
• 6261-32-1 2-benzylidene-1-tetralone 
• 529-20-4 2-methylphenyl aldehyde 
• 85679-03-4 1-phenylnaphthalene-2-carboxylic acid 
• 7440-05-3 palladium 
• 108-86-1 bromobenzene 
• 20199-35-3 di(2-naphthyl)acetylene 
• 4590-03-8 1,2,9,9a-tetrahydro-fluoren-3-one 
• 18937-92-3 1-(2-bromophenyl)naphthalene 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1528732-84-4 1-(2-(cyclohepta-2,4,6-trien-1-yl)phenyl)naphthalene 
• 1106670-81-8 1-(2-bromophenyl)-2-methylnaphthalene 
• 1037085-12-3 1-[2-(chloromethyl)phenyl]naphthalene 
• 109644-44-2 10-oxo-7a,8,9,10-tetrahydro-7H-benzo[c]fluorene-9-carboxylic acid ethyl ester 

Downstream Products

• 112486-09-6 7,7-Dimethyl-7H-benzo[c]fluorene 
• 74869-35-5 5,6-dimethyltetrahelicene 
• 27921-62-6 9-(o-Chlorbenzoyl)benzofluoren 
• 27921-57-9 5-(o-Chlorbenzoyl)benzofluoren 
• 5385-22-8 naphth[1,2-e]acephenanthrylene 
• 5385-75-1 dibenzo[a,e]fluoranthene 
• 100354-05-0 7-Acetyl-7-methyl-benzofluoren 

Relevant articles and documents

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Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp2)-H Bond Functionalization

A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C-C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source. Metal carbene migratory insertion and C(sp2)-H bond activation are proposed as the key steps in this transformation. The reaction further demonstrates the versatility of the carbene-based coupling in combination with various transition-metal-catalyzed transformations.

Gold(I) carbenes by retro-buchner reaction: Generation and fate

The fate of the aryl gold(I) carbenes generated by retro-Buchner reaction of ortho-substituted 7-aryl-1,3,5-cycloheptatrienes is dependent on the constitution of the ortho substituent. Indenes and fluorenes are obtained by intramolecular reaction of highly electrophilic gold(I) carbenes with alkenes and arenes. According to density functional theory calculations, the gold-catalyzed retro-Buchner process occurs stepwise, although the two carbon-carbon cleavages occur on a rather flat potential energy surface.

Highly efficient and versatile synthesis of polyarylfluorenes via Pd-catalyzed C-H bond activation

A facile protocol for the Pd-catalyzed preparative synthesis of fluorene derivatives has been developed. While a wide range of fluorenes were easily obtained with high efficiency and selectivity under mild conditions, excellent functional group tolerance