201-65-0

Usage

Chemical class

Polycyclic aromatic hydrocarbon (PAH)

Physical state

White, crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Presence

Found in coal tar, soot, and crude oil

Formation

Formed during the incomplete combustion of organic materials, such as tobacco smoke and vehicle exhaust

Health hazards

Potential carcinogen and mutagen

Health risks

Associated with carcinogenic and mutagenic effects

Precaution

Minimize exposure to reduce associated health risks

InChI:InChI=1/C21H14/c1-2-8-15-14(7-1)13-20-18-11-4-3-9-16(18)17-10-5-6-12-19(17)21(15)20/h1-12H,13H2

Upstream product

• 408331-25-9 spiro[fluorene-9,2'-indan]-1'-ol 
• 7080-31-1 13H-1,2,3,4,5,6,7,8-octahydrobicyclohexafluorene 
• 562834-87-1 2,3,4,5,6,7,8,8a,8b,13,13a,13b-dodecahydro-1H-indeno[1,2-l]phenanthrene 
• 98509-50-3 3-biphenyl-2-yl-indene 
• 859816-59-4 1-(2-[9]phenanthryl-ethyl)-cyclopentanol 
• 5324-00-5 2,3-diphenyl-1H-indene 
• 966-87-0 1,1,3-triphenylpropa-1,2-diene 
• 4467-88-3 1,3-diphenylindene 
• 13029-09-9 2,2'-dibromobiphenyl 
• 102456-48-4 1(tri-n-butylstannyl)indene 
• 20033-18-5 13H-Indeno[1,2-l]phenanthrene-13-carboxylic acid methyl ester 
• 76773-35-8 1,3-diphenyl-1-indenol 
• 80654-81-5 13H-1,2,3,4,5,6,7,8,13a,13b-decahydrobicyclohexafluorene 
• 2236-52-4 2,2'-diiodobiphenyl 

Relevant academic research and scientific papers

Palladium-Catalyzed Coupling of 2,2'-Dihalobiaryls with Metallated Cyclopentenes. An Easy Synthesis for SpiroFluorene>s

In the presence of palladium catalysts, one of the two carbons attached to halogen in 2,2'-diiodobiphenyl couples with unsaturated organometallics, after which the other adds to the newly incorporated double bond.Spirofluorene>s can be synthesized in this way.

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.

Palladium-catalyzed double cross-coupling reaction of vic-diborylalkenes and -arenes with vic-bromo(bromomethyl)arenes

Efficient annulation of vic-diborylalkenes and -arenes with vic-bromo(bromomethyl)arenes has been achieved, using Pd(PPh3) 4 as a catalyst in the presence of Cs2CO3 and water in THF at 60°C, giving rise to the c

Joining the rings: The preparation of 2- and 3-indenyl-triptycenes, and curious related processes

The indenyltriptycenes, 1 and 2, where the 3- or 2-indenyl, respectively, is attached at the 9-position of the triptycene, are attractive prototypes of molecular gearing systems that can also incorporate a brake. These molecules have been prepared from their respective indenylanthracenes, 3 and 4, by the [4 + 2] cycloaddition of benzyne to the anthracene fragment, and the rotational barriers about the indenyl-triptycenyl single bonds in 1 (12 kcal mol -1) and 2 (-1) have been measured. The precursor anthracenes, 3 and 4, were prepared by using palladium-catalysed coupling reactions. Unexpectedly, the Heck-type reaction of 9-bromoanthracene, 5, with indene leads to the formation of 3-indenylanthracene 3; moreover, this process is accompanied by a novel palladium-catalysed carbocyclisation reaction leading to the indenophenanthrylene 9. The addition of benzyne to 9-(3-indenyl)anthracene, 3, yields the corresponding indenyltriptycene, 1, and, surprisingly, the anthracenyl methano-bridged phenanthrene 16. It has been demonstrated that 2-arylindenes can act as 1,3-dienes in the [4 + 2] cycloadditions of benzyne. The products 2, 7a, 9 and 16 have been characterised by X-ray crystallography. The Royal Society of Chemistry.

An Efficient Synthesis of Benzofluorenes Via α-Alkoxycarbonyldiarylmethyl Cations

Rearrangement of α-alkoxycarbonyldiarylmethyl cations lead to 9-fluorenecarboxylic esters.Decarboxylation of these esters generates the fluorene derivatives 9a-f.The precursors to the cations are the α-hydroxyesters 6a-g.This conversion constitutes a facile synthesis of benzofluorenes.

CUMULENE PHOTOCHEMISTRY: PHENYL AND HYDROGEN MIGRATION IN PHENYLALLENE PHOTOREACTIONS

Photoreactions of tetra- and triphenylallene and 1,3,3-triphenylcyclopropane in hydrocarbon solvents are reported.Intermediacy of vinylcarbenes is supported by independent generation experiments.

Sigmatropic Indenyl Rearrangements Induced by Electronic Excitation

The photochemical rearrangement of several arylalkyl substituted indenes has been studied.The rearrangements were shown to be derived from the ?,?* singlet state since triplet sensitization led to no reaction or else resulted in a Paterno-Buchi

Polycyclic Aromatic Compounds : Part VI - Synthesis of Dicyclopentafluorene and Dibenzofluorene Derivatives

A series of fluorene derivatives have been synthesised by the dehydrogenation of the adducts, obtained by the condensation of various alicyclic dienes, viz. 1:1'-bicyclopentenyl (I), 1:1'-bicyclohexenyl (IIa, R = R1= H), 4,4'-dimethyl-1:1'-bicyclohexenyl (IIb, R = CH3, R1 = H), 5,5'-dimethyl-1:1'-bicyclohexenyl (IIc, R = H, R1 = CH3), 3,3',4,4'-tetrahydro-1:1'-dinaphthyl (III) and perylene (IV) with 1-chloro-3H-indene.The hydrocarbon, 13H-fluorenoperylene (XXIII), has been prepared by two different routes.A few fluorenone derivatives have also been prepared by the cyclisation of the aromatized adducts, obtained by the condendation of the dienes with phenylpropiolic acid.