89523-51-3

Basic information

• Product Name: 5-BroMo-Benzo[c]phenanthrene
• Synonyms: 5-BroMo-Benzo[c]phenanthrene;5-BroMo-Benzo[c]phenthrene
• CAS NO: 89523-51-3
• Molecular Formula: C₁₈H₁₁Br
• Molecular Weight: 307.18394
• Mol File: 89523-51-3.mol

Chemical Properties

• Melting Point: 76.6-77.6℃
• Boiling Point: 482.9±14.0 °C(Predicted)
• Appearance: /
• Density: 1.477±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-BroMo-Benzo[c]phenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BroMo-Benzo[c]phenanthrene(89523-51-3)
• EPA Substance Registry System: 5-BroMo-Benzo[c]phenanthrene(89523-51-3)

Safety Data

• Hazardous Substances Data: 89523-51-3(Hazardous Substances Data)

Usage

Uses

Used in Medicinal and Pharmaceutical Research:
5-Bromo-Benzo[c]phenanthrene is used as a research compound for exploring its potential applications in medicinal and pharmaceutical research. Its unique molecular structure and chemical properties make it a valuable compound for investigating its potential biological activities and therapeutic effects.
Used in Chemical Synthesis:
5-Bromo-Benzo[c]phenanthrene can be used as a starting material or intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional groups can be exploited in various chemical reactions to produce desired products.
Used in Material Science:
Due to its unique chemical properties, 5-Bromo-Benzo[c]phenanthrene may have potential applications in material science, such as in the development of new materials with specific properties, like conductivity, stability, or reactivity. Further research is needed to explore its potential in this field.
Used in Environmental Research:
5-Bromo-Benzo[c]phenanthrene may also have potential applications in environmental research, such as in the study of environmental pollutants, their degradation pathways, or their impact on ecosystems. Its unique properties could provide insights into the behavior of similar compounds in the environment.
Used in Analytical Chemistry:
As a chemical compound with distinct properties, 5-Bromo-Benzo[c]phenanthrene can be used as a reference material or standard in analytical chemistry for the development and validation of analytical methods, such as chromatography, spectroscopy, or mass spectrometry.

Upstream product

• 195-19-7 benzo[c]phenathrene 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 115009-86-4 2-dibromomethyl-1-(2-dibromomethyl-phenyl)naphthalene 
• 93870-58-7 1-(2'-methylphenyl)-2-methylnaphthalene 
• 1155911-73-1 2-(4-bromonaphthalen-1-yl)benzaldehyde 
• 83-53-4 1,4-dibromonaphthalene 
• 40138-16-7 2-formylbenzene boronic acid 
• 1155911-74-2 1-bromo-4-[1-(2-methoxyvinyl)phenyl]naphthalene 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 89523-47-7 trans-5-bromo-6-acetoxy-5,6-dihydrobenzophenantherene 
• 99901-85-6 trans-5,6-dibromo-5,6-dihydrobenzophenanthrene 

Downstream Products

• 1155911-83-3 9-(phenyl)-10-(benzo[c]phenanthren-5-yl)anthracene 
• 1315500-79-8 C₃₇H₂₄N₂ 
• 1236211-20-3 5-(diphenylamino)benzo[c]phenanthrene 
• 195-19-7 benzo[c]phenathrene 
• 4176-50-5 benz[c]phenanthren-5-ylamine 

Relevant articles and documents

Absolute Configuration of Benzophenanthrene 5,6-Oxide and Other K-Region Derivatives

Synthesis of enantiomerically pure benzophenanthrene (+)-(5S,6R)- and (-)-(5R,6S)-oxides is described from diastereomerically pure (-)-(5R,6R)-trans-5-bromo-6-- and (+)-(5S,6S)-trans-5 bromo-6--5,6-dihydrobenzophenanthrene derived from (-)-(menthyloxy)acetic acid.Configurational assignment of the enantiomeric arene oxides is based on correlation of the CD spectra of their trans-N-acetyl-L-cysteine adducts as methyl esters with the bis(-)-α-methoxy(trifluoromethyl)phenylacetate) of (+)-(5R,6R)-trans-5,6-dihydroxy-5,6-dihydrobenzophenanthrene of known absolute configuration.Separable major and minor S adducts were obtained from each arene oxide enantiomer.Structures of the major (attack at C-6) and minor (attack at C-5) adducts were established through the use of 5-deuterated arene oxide.Predominant attack (3:1) of the thiolate at C-6 of the arene oxide is consistent with PMO calculations.

Palladium-catalyzed annulation of 9-halophenanthrenes with alkynes: Synthesis, structural analysis, and properties of acephenanthrylene-based derivatives

The palladium-catalyzed annulation of 9-bromoand 9-chlorophenanthrenes with alkynes gave 4,5-disubstituted acephenanthrylenes in yields of 58-95% (9 examples). Asymmetric alkynes, such as 1-phenyl-1-propyne, 1-phenyl-1-hexyne, and 1-cyclopropyl-2-phenylethyne, regioselectively form (cyclo)alkyl-substituted products, following the regular rule that governs the carbopalladation of alkynes. This synthetic protocol can also be utilized in annulations with several p-extended bromoarenes, such as 7-bromo[5]helicene, 5-bromo[4]helicene, 9-bromoanthracene, 3-bromoperylene, and 3-bromofluoranthene, to give the corresponding annulated products in moderate to good yields (51-86%; 6 examples). Similarly, bromocorannulene produced highly curved 1,2-disubstituted cyclopentacorannulenes. Reactions of 6,12-dibromochrysene and 4,7-dibromo[4]helicene with di(4-tolyl) ethyne provided the twofold annulated products in moderate yields. 4,5-Diphenylacephenanthrylene and 6,7-diphenylbenzo[ a]acephenanthrylene thus generated were converted into phenanthro[9,10-e]acephenanthrylene and benzo[ a]phenanthro[9,10-e]acephenanthrylene, respectively, by oxidative cyclodehydrogenation. The structures of 4,5-diphenylacephenanthrylene, 4,5-diphenyldibenzo[a,l]acephenanthrylene, 1,2-diarylcyclopentacorannulenes, and benzo[ a]-phenanthro[9,10-e]acephenanthrylene were verified by X-ray crystallography. The photophysical and electrochemical properties of the selected annulated products were investigated.

NITROGEN-CONTAINING HETEROCYCLIC DERIVATIVE, ORGANIC ELECTROLUMINESCENCE ELEMENT MATERIAL USING SAME, AND ORGANIC ELECTROLUMINESCENCE ELEMENT AND ELECTRONIC DEVICE USING SAME

Indole structure, benzo [...] coupled a nitrogenous heterocyclic derivative represented by formula 1, using the same material for organic electroluminescence device, and and electronic organic electroluminescent device using the device, organic electroluminescence device a novel material provides. [Formula 1] [In formula 1, R 1 ～ R 12 the, independently, hydrogen atom or methyl group, R 1 ～ R 12 subsets such that adjacent selected from dog 2, is provided to be easily assembled and of saturated or unsaturated forming a ring 2 may forming the group. Stage, R 1 ～ R 12 2 subsets such that adjacent selected from at least of a sol 1, is provided to be easily assembled and, a ring represented by formula a form a heterogeneous phase structure.. [Formula a] R 13 ～ R 17 the, independently, hydrogen atom or methyl group, R 13 ～ R 17 subsets such that adjacent selected from dog 2, forming a ring is provided to be easily assembled and saturated or unsaturated of forming the group 2 may.] (by machine translation)

NITROGENATED HETEROCYCLIC RING DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT COMPRISING SAME

A nitrogen-containing heterocyclic derivative represented by the following formula (1): wherein any "12-a" groups of R1 to R12 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; any "a" groups of R1 to R12 are independently a single bond which is bonded to L1; L1 is a single bond, a "b+1" valent substituted or unsubstituted hydrocarbon ring group having 6 to 30 ring carbon atoms or a "b+1" valent substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group; and "a" and "b" are independently an integer of 1 to 4, and at least one of "a" and "b" is 1. Also disclosed is a nitrogen-containing heterocyclic derivative represented by the following formula (21) or (31):

BENZOPHENANTHRENE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE EMPLOYING THE SAME

A fused aromatic ring derivative shown by the following formula (1): wherein Ra and Rb are independently a hydrogen atom or a substituent, p is an integer of 1 to 8 and q is an integer of 1 to 11, when p is 2 or more, plural Ra

High temperature gas phase syntheses of C20H12 cyclopenta-fused polycyclic aromatic hydrocarbons: Benz[l]acephenanthrylene and benz[j]acephenanthrylene and their selective rearrangement to benzo[j]fluoranthene

The novel C20H12 cyclopenta-fused polycyclic aromatic hydrocarbon benz[l]acephenanthrylene (2) and its isomer benz[j]acephenanthrylene (3) have been obtained by flash vacuum thermolysis of 2-(1-chloroethenyl)benzo[c]phenanthrene (6) and 6-(1-chloroethenyl)chrysene (7), respectively. At T ≥ 900°C 2 and T ≥ 1000°C 3 rearrange selectively to the abundant combustion effluent benzo[j]-fluoranthene (1). No evidence for the presence of the related rearrangement products benz[l]aceanthrylene (12) and benz[j]aceanthrylene (13), respectively, is found. Semi-empirical AM1 calculations provide a rationalization for these observations; the conversion of 2 and 3 into 1, instead of 12 and 13, respectively, via consecutive ring-contraction-ring-expansion processes and vice versa is favoured.

Synthesis of the K-Region Monofluoro- and Difluorobenzophenanthrenes

Polycyclic aromatic hydrocarbons are metabolically activated by cytochromes P-450 an epoxide hydrolase to ultimate mutagens and carcinogens.Substitution by fluorine at specific positions has been used to elucidate metabolic activation and detoxication pathways of polycyclic aromatic hydrocarbons.Substitution by fluorine at the K-region C-6 position of the weak carcinogen benzophenanthrene (1) causes a >4-fold increase in its tumorigenicity.Out of the six possible monofluorobenzophenanthrenes, only 5-fluorobenzophenanthrene (8a) has not been evaluated as a carcinogen, presumably because a convenient synthetic method for the 5-fluoro derivative has not been available.Hence, a new method has been developed for the synthesis of 8a from readily available starting materials.The method consists of selective bromination of benzophenanthrene (1) to 5-bromobenzophenanthrene (3), substitution of bromine by an amino group, and a modified Schiemann reaction of 5-aminobenzophenanthrene (6a) to yield 5-fluorobenzophenanthrene (8a).An improved method for the synthesis of 6-fluorobenzophenanthrene (19) has also been developed which consist of bromofluorination of β-naphthylstyrene, followed by selective dehydrobromination and photocyclization of the fluorostyrene to the 6-fluoro derivative 19.The above methods, with minor modifications, also provided synthetic routes for the preparation of the difluoro derivatives 5,7-, 5,8-, and 6,7-difluorobenzophenanthrenes.

FACILE SYNTHESIS OF K-REGION ARENE OXIDES

Polycyclic aromatic hydrocarbons reacts at the K-region with N-bromoacetamide in acetic acid to provide trans-bromohydrin acetates which are readly cyclized to arene oxides.The simplicity of the approach makes radioactive and optically active K-region arene oxides easily available.