53034-15-4

Basic information

• Product Name: 2-BROMOBENZO[C]PHENANTHRENE
• Synonyms: 2-BROMOBENZO[C]PHENANTHRENE
• CAS NO: 53034-15-4
• Molecular Formula: C₁₈H₁₁Br
• Molecular Weight: 307.18
• Mol File: 53034-15-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BROMOBENZO[C]PHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOBENZO[C]PHENANTHRENE(53034-15-4)
• EPA Substance Registry System: 2-BROMOBENZO[C]PHENANTHRENE(53034-15-4)

Safety Data

• Hazardous Substances Data: 53034-15-4(Hazardous Substances Data)

Upstream product

• 53034-13-2 1-(p-bromophenyl)-2-(2-naphthyl)ethylene 
• 38186-51-5 diethyl (4-bromobenzyl)phosphonate 
• 53034-14-3 (Z)-1-(p-bromophenyl)-2-(2-naphthyl)ethylene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 51044-13-4 4-bromobenzyl triphenylphosphonium bromide 
• 53034-14-3 (E)-1-(4-bromophenyl)-2-(2-naphthyl)ethylene 
• 66-99-9 β-naphthaldehyde 

Downstream Products

• 1178511-85-7 C₂₆H₁₇Br 
• 32829-04-2 2-styrylbenzo[c]phenanthrene 
• 67213-08-5 2-[2-(4-methylphenyl)ethenyl]benzo[c]phenanthrene 
• 187-83-7 [6]helicene 
• 1380650-22-5 C₂₉H₂₂O₂ 
• 41866-94-8 2-[(E)-2-(4-Methoxy-phenyl)-vinyl]-benzo[c]phenanthrene 
• 20508-12-7 (E)-1-Phenyl-2-(2-benzophenanthrenyl)ethylene 
• 120233-65-0 2-phenylbenzo[c]phenanthrene 
• 195-19-7 benzo[c]phenathrene 
• 203-12-3 benzo[ghi]fluoranthene 

Relevant articles and documents

Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings

The first racemization-stable helicene derivatives fluorinated at terminal rings, 1,2,3,4-tetrafluoro[6]helicene (6) and 1,2,3,4,13,14,15,16-octafluoro[6]helicene (15), were synthesized via the Wittig reaction followed by oxidative photocyclization in an

Direct Wittig Olefination of Alcohols

A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination products. By the strategy of simultaneously in situ generation of ylides and aldehydes, for the first time, alcohols are directly transferred to olefins with no need of prepreparation of either aldehydes or ylides. Thus, the di/monocontrollable olefination of diols is accomplished. This synthetically practical method has been applied in the gram-scale synthesis of pharmaceuticals, such as DMU-212 and resveratrol from alcohols.

2-Bromo[6]helicene as a Key Intermediate for [6]Helicene Functionalization

The synthesis of 2-bromo[6]helicene was revised and improved up to 51% yield. Its reactivity was thoroughly investigated, and a library of 17 different carbon, boron, nitrogen, phosphorus, oxygen and sulfur substituted derivatives was prepared. The racemization barrier for 2-bromo[6]helicene was determined, and the usage of enantiomers in the synthesis of optically pure helicenes was rationalized. The three most energy-demanding reactions using enantiomerically pure 2-bromo[6]helicene were tested in order to confirm the predicted enantiomeric excess.

Surface-assisted diastereoselective Ullmann coupling of bishelicenes

Ullmann coupling of chiral 2-bromo[4]helicene has been performed on a Cu(100) surface. Only homochiral 2,2′-bis[4]helicene as the product is observed using STM. Such stereoselectivity is based on the fact that the surface will favour a configuration with

Synthesis and characterization of a new hexacyclic helicene

A new helically chiral hexacyclic system, bearing an acetoxymethyl group, was prepared from a simple naphthalene building block in good yield and purity, via a four-step sequence involving palladium-catalysed Heck couplings and oxidative photocyclizations

1H-phosphindoles as structural units in the synthesis of chiral helicenes

Building helicenes: A photochemical cyclization approach affords helicenes in which the fused ring sequence ends with a phosphole unit (see scheme). The stereogenic phosphorus centers of the substrates control the screw sense of helical chirality. The terminal phosphole units undergo photochemical [2+2] annulations to give dimeric helical structures. Copyright

Expeditious synthesis of helicenes using an improved protocol of photocyclodehydrogenation of stilbenes

An improved procedure has been developed for photodehydrocyclization of stilbenes for the synthesis of phenanthrenes and helicenes. This procedure involves the use of THF as a scavenger of hydriodic acid produced during iodine mediated photodehydrocyclization. The use of THF is advantageous due to its higher boiling point, lower cost and easy availability as compared to propylene oxide. The method is applied to synthesize a number of phenanthrenes and helicenes. ARKAT-USA, Inc.

Synthesis of derivatives of phenanthrene and helicene by improved procedures of photocyclization of stilbenes

An improved method has been developed for photocyclization of stilbene to construct phenanthrenes and benzo[c]phenanthrenes. This reaction is promoted by iodine while tetrahydrofuran is used as an efficient and inexpensive scavenger of hydroiodic acid produced during the photocyclization sequence. In another process, cyclohexene is used as a reagent for dehydrogenation step in place of THFI2.

Synthesis of a new N-containing hexahelicene

A new helically chiral hexacyclic system, containing one pyridine unit, was prepared through a four-step synthesis involving palladium promoted Mizoroki-Heck couplings and classical oxidative photodehydrocyclisation.

1,2-shifts of hydrogen atoms in aryl radicals

An energy barrier on the order of 60 kcal/mol is predicted for the 1,2- shift of hydrogen atoms in aryl radicals. Such rearrangements are, therefore, not expected to occur under ordinary laboratory conditions, but they should be prevalent in the aryl radicals formed during combustion, flash vacuum pyrolysis, and other high-temperature gas-phase processes. As a demonstration of this rearrangement, the 2-benzo[c]phenanthryl radical (1) was generated by flash vacuum pyrolysis of the corresponding aryl bromide (9). A 1,2-shift of hydrogen out of the sterically congested cove region of 1, followed by cyclization and rearomatization of the resulting radical (Scheme 1), is proposed to explain the observation of benzo[ghi]fluoranthene (4) as the dominant monomeric product formed. Under the same conditions, [ 1,3,4,5- 2H4]-2-bromobenzo[c]phenanthrene (13) gives [ 1,2,3,4-2H4]- benzo[ghi]fluoranthene (15) as the dominant monomeric product (Scheme 6), in accord with the expectation of a deuterium atom 1,2-shift.