1.2- Benzanthracene

Synonyms BA benzanthracene 1,2-benz( z)anthracene benzo( z)anthracene 2,3-benzophenanthrene naphthanthracene tetraphene 

Physical Form. Solid often associated with or adsorbed onto ultrafine airborne particulate matter 

Plates form from glacial acetic acid or ethanol.1 Greenish-yellow fluorescence. Sublimes mp, 159-16rC2 bp,437.6°C.1 

Insoluble in water slightly soluble in boiling ethanol soluble in most other organic solvents.1 

Carcinogen in mice.2 Lowest toxic doses (mice) at 2 mg/kg (subcutaneous), 4 mg/kg/15 weeks (oral) and 240 mg/kg/15 weeks (skin).3,4 Animal carcinogen reasonably anticipated to be human carcinogen. Exposure by all routes should be carefully controlled to the lowest possible levels.4 

Wear protective gloves and clothing, goggles, and breathing apparatus if necessary. Turn off all ventilation and isolate spill area. Add enough dimethylformamide to completely wet the contaminated surface, and then pour over the area an excess of freshly prepared solution containing 4.7 g of potassium permanganate in 100 mL of 3 M sulfuric acid (17 mL of concentrated sulfuric acid slowly added to 83 mL of cold water). Allow to react for at least 1 hour. Cover the residual solution with a 1 1 1 of soda ash, clay cat litter 

Package Lots. Place in a separate labeled container for disposal by burning.7 

The Grignard reagent is prepared in normal manner [Org. Syntheses Coll. Vol. 1, 226 (1941)] from 50 g. (0.24 mole) of 1-bromo-naphthalene in 75 ml. of ether and 75 ml. of benzene. To this is added 23.4 g. (0.20 mole) of o-tolunitrile [Org. Syntheses Coll. Vol. 1, 514 (1941)], and the mixture refluxed for 8 hours followed by addition of ice and 100 ml. of concentrated hydrochloric acid. The precipitated solid is removed by filtration and boiled with water for 1 hour. The solid precipitated upon cooling is distilled to give 37.8 g. (76%) of 1-naphthyl o-tolyl ketone, b.p. 174°/0.4 mm., m.p. 59-61°. 

A mixture of 34 g. (0.14 mole) of the ketone and 10 g. of zinc dust is heated for 3 hours in a metal bath at a bath temperature of 410°. The material is then heated in a distillation system at 0.4 mm. pressure. The hydrocarbon distilled is recrystallized several times from benzene-ethanol mixture to give 17.2 g. (54%) of 1,2-benzanthracene. Product melting at 155.5-157° is obtained by solution of the 17.2 g. and 1 g. of maleic anhydride in 50 ml. of benzene, refluxing for 3 hours, extraction of the hot solution with aqueous sodium hydroxide solution, 

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Naphthacene (benz[b]anthracene, 2,3-benzanthracene, rubene) [92-24-0] M 228.3, m >300 , 341 (open capillary), 349 , 357 . Crystd from EtOH or benzene. Dissolved in sodium-dried benzene and passed through a column of alumina. The benzene was evaporated under vacuum, and the chromatography was repeated using fresh benzene. Finally, the naphthacene was sublimed under vacuum. [Martin and Ubblehode J Chem Soc 4948 7967.] Also recrysts in orange needles from xylene and sublimes in vacuo at 186°. [UV Chem Ber 65 517 1932, 69 607 7956 IR Spectrochim Acta 4 373 7957.]... 

Figure 1. Effect of potential inducing agents on certain hepatic microsomal enzymes of the rainbow trout. Animals were infected intraperitoneally with either phenobarbital (65 mg/kg) 3-methylcholanthrene (20 mg/kg) 2,3-benzanthracene (10 mg/kg) or /3-naphthoflavone (100 mg/kg). The animals were sacrified and hepatic microsome prepared 48 hr after infection. Each bar is the mean SE (n = 3-5) ( ), induced activity (T) significantly different from control (C) activity...

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 ... 

Benzanthracene, see Benzo[a]anthracene 1,2 5,6-Benzanthracene, see Dibenz[a,//]anthracene Benzanthrene, see Benzo[a]anthracene... 

Figure 15.3 Electronic absorption spectra of (a) naphthalene, (b) anthracene, (c) phenanthrene, (d) 2,3-benzanthracene (naphthacene), and (e) 1,2-benzanthracene (benz(a)-anthracene) (data from Pretsch et al., 2000).

The reactions of Cp(Sm(THF)2 with a variety of alkenes in hexane or toluene solvent to produce allyl and alkene products have been studied. Binuclear Sm complexes have been synthesized [159] by the reaction of Cp Sm with pyrene, anthracene, 2,3-benzanthracene, 9-methylanthracene. The structure of the complex [(Cp Sm)2(/r-/73 /73-CioHi4)] is shown in Fig. 6.16. 

A similar experiment in [C2mim][N(Tf)2] was conducted on a family of arenes, such as pyrene (vii), perylene (viii), chrysene (ix), 1,2-benzanthracene (x), and 2,3-benzanthracene (xi) [9]. For all these compounds, a radical-substrate coupling (RSC) mechanism (Eqs. 15.6-15.9) was observed, instead the radical-radical coupling (RRC) mechanism observed for anthracenes. Uniquely, viii was excellently modelled by a simple E reaction mechanism [9]. 

Complexes of bridging, reduced polycyclic arenes with more than three fused phenyl rings were also reported and various coordination modes identified (Chart 17). These range from (Cp 2Sm)2(p-ri ri -Ci6Hio) (Evans et al., 1994) to [(Cp La)3(p-Cl)3(THF)(p-ri2 ri ri -Ci6Hio)] (Thiele et al., 1998) in pyrene compounds and (Cp 2Sm)2(p-ri ri -CigHi2) (Evans et al., 1994) in a 2,3-benzanthracene complex. 

CHART 17 Bridging, dianionic pyrene and 2,3-benzanthracene rare earth complexes. 

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