Benz anthracenes

The arene (5 mmol) in CHCl3 (100 ml) is added to aqueous NaOCl (0.6 M, 250 ml) and the pH is adjusted to 8-9 by the addition of cone. HCl. TBA-HS04 (0.34 g, l mmol) is added and the mixture is stirred until TLC analysis shows complete conversion of the arene. The organic phase is separated, washed well with H20, dried (K2CO ), and evaporated to yield the epoxide (e.g. 90% from phenanthrene, 76% from 1,2-benz-anthracene, 70% from acenaphthene, 19% 2,3 4,5-bis-epoxide from naphthalene). 

Synonyms AI3-50599 BA B(a)A Benzanthracene Benz[ ]anthracene 1,2-Benzanthracene 1,2-Benz[a]anthracene 2,3-Benzanthracene Benzanthrene 1,2-Benzanthrene Benzoanthracene 1,2 Benzoanthracene Benzo[a]phenanthrene Benzo[6]phenanthrene 2,3-Benzophenanthrene CCRIS 69 EINECS 200-280-6 Naphthanthracene NSC 30970 RCRA waste number U018 ... 

Sources. Benz[ ]anthracene is a major component of the total content of polynuclear aromatic hydrocarbons, also known as polycyclic aromatic hydrocarbons human exposure occurs primarily through smoking of tobacco, inhalation of products of incomplete organic combustion such as automobile exhaust, and ingestion of food contaminated by combustion effluents such as those that are smoked or barbecued. 

Benz( )anthracene is designated an A2-suspected human carcinogen by ACGIH and has no assigned threshold limit value. 

PAHs also generally have well-structured emission spectra (see Figs. 10.6-10.10) and relatively large fluorescence quantum yields. For example, in degassed n-heptane at room temperature, the fluorescence quantum yields are as follows fluoranthene, 0.35 benz[ ]anthracene, 0.23 chrysene, 0.18 BaP, 0.60 BeP, 0.11 and benzo[g/zi]perylene, 0.29 (Heinrich and Giisten,1980). Cyclopenta[crf]pyrene, however, does not fluoresce. 

Benz( )anthracene is also converted in the body to a carcinogenic epoxide (Eq. 27-28).793 Benzo(a)pyrene was isolated from coal tar in 1929 and in 1930 provided the first demonstration of the carcinogenicity of a pure chemical compound.794 It can also be activated by conversion in the ER to the 7,8-dihydrodiol 9,10-... 

In a recent comprehensive study with respect to the substituent effects of benz anthracene carbocations,280 exclusive protonation at C(7) (102) and C(12) (103, bay region protonation) in the C ring was shown to occur. The relative stability of the resulting carbocations, however, strongly depends on the substitution pattern. Substrates methyl-substituted in the A ring give mixtures of the two cations. Protonation of 5-, 6-, and 7-methyl- and 7-ethyl-substituted compounds, in turn, yields... 

Being interested here in the volatile components of coffee aroma, we shall arbitrarily limit the list of the aromatic hydrocarbons to tricyclic structures. The higher fused polycyclic hydrocarbons (fluoranthene [206-44-0], pyrene [129-00-0], chrysene [218-01-9], benz[ ]anthracene (1,2-benzanthracene) [56-55-3], benz[< ]acephenanthrylene (3,4-benzofluoranthene) [205-99-2], benzo[ ]pyrene (3,4-benzopyrene, 3,4-BP) [50-32-8], benzo[e]pyrene (1,2-benzopyrene) [192-97-2], perylene [198-55-0], benzo[g,/i,/]perylene (1,12-benzopyrene) [191-24-2], and dibenz[ ,//]anthracene (1,2,5,6-dibenzanthracene) [53-70-3]) cannot be considered as a part of the aroma. However, as some of these, specially benzo[o pyrene, are known for carcinogenic properties, they have been particularly analyzed in food subject to roasting or smoke-curing. 

This reaction has some importance for the preparation of derivatives of anthracene,980 dibenz[a,h]anthracene,981 benz[ anthracene,982 and chol-anthrene.983... 

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