10273-74-2

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Chemical Properties

WHITE CRYSTALLINE POWDER

InChI:InChI=1/C44H38P2.2BrH/c1-7-19-39(20-8-1)45(40-21-9-2-10-22-40,41-23-11-3-12-24-41)35-37-31-33-38(34-32-37)36-46(42-25-13-4-14-26-42,43-27-15-5-16-28-43)44-29-17-6-18-30-44;;/h1-34H,35-36H2;2*1H/q+2;;/p-2

Upstream product

• 603-35-0 triphenylphosphine 
• 626-15-3 1,3-bis-(bromomethyl)benzene 

Downstream Products

• 10273-76-4 1,3-Bis-((1E,3E)-4-phenyl-buta-1,3-dienyl)-benzene 
• 99367-23-4 cis-cis 1,3-bis<2-(2-ethynylphenyl)ethenyl>benzene 
• 99367-24-5 cis-trans 1,3-bis<2-(2-ethynylphenyl)ethenyl>benzene 
• 99367-25-6 trans-trans 1,3-bis<2-(2-ethynylphenyl)ethenyl>benzene 
• 145260-17-9 1,3-bis(1,2-dideoxy-3,4,5-tri-O-methyl-D-xylo-hexitolyl)benzene 
• 145260-15-7 1,3-bis(1,2-dideoxy-4,6-O-phenylmethylene-3,5-O-methylene-L-xylo-hexitolyl)-benzene 
• 145260-14-6 1,3-bis((Z)-1,2-dideoxy-4,6-O-phenylmethylene-3,5-O-methylene-L-xylo-hex-1-enitolyl)-benzene 
• 145260-14-6 1,3-bis(1,2-dideoxy-4,6-O-phenylmethylene-3,5-O-methylene-L-xylo-hex-1-enitolyl)-benzene, Z,E-isomer 
• 99367-12-1 trans-trans 1,3-bis(4-methyldodeca-1,3-diene-5-ynyl)benzene 
• 99367-12-1 cis-cis 1,3-bis(4-methyldodeca-1,3-diene-5-ynyl)benzene 
• 99367-12-1 cis-trans 1,3-bis(4-methyldodeca-1,3-diene-5-ynyl)benzene 
• 1232394-64-7 1,3-bis[(triphenylphosphonio)methanido]benzene bis(pentafluorophenyl)gold(I) 
• 64984-67-4 1,3-Bis-(α-bromvinyl)-benzol 
• 111220-68-9 1,3-bis(8-methyldeca-1,3,5,7-tetraen-9-ynyl)benzene 

Relevant academic research and scientific papers

FORMATION OF A DINAPHTHANTHRACENE BY A STILBENE-LIKE PHOTOCYCLIZATION

Photocyclization of 1,3-bisbenzene leads regioselectively to dinaphthanthracene without the need for a blocking bromine substituent at C-2 in the starting material as assumed previously by other workers.

Synthesis of potentially carcinogenic higher oxidized metabolites of dibenz[a,j]anthracene and benzo[c]chrysene

Bis(dihydrodiols) and other higher oxidized metabolites are implicated as active carcinogenic metabolites of polycyclic aromatic hydrocarbons, such as dibenz[a,j]anthracene, that possess more than one bay region in the molecule. The bis(dihydrodiol) metabolites may potentially undergo further metabolism to mono- or diepoxides that combine covalently with DNA or undergo conversion to bis(catechols) that enter into a redox cycle with O2 to form reactive oxygen species that attack DNA. This paper reports convenient syntheses of the terminal ring bis(dihydrodiol) derivatives of dibenz[a,j]anthracene (5) and benzo[c]chrysene (6) via routes that involve in the key steps double oxidative photocyclization of tetramethoxy-substituted diolefins. The latter are synthesized via double Wittig reaction of a bis(phosphonium) salt with 2,3-dimethoxybenzaldehyde. Demethylation of the bis(catechol) products followed by acetylation and reduction with NaBH4 in the presence of O2 affords the bis(dihydrodiol) products. Several additional higher oxidized derivatives of dibenz[a,j]anthracene, specifically the 3,11- diphenol (14a), the 11-hydroxy-3,4-quinone (15), and the 11-hydroxy-trans- 3,4-dihydrodiol (2c), are obtained by an alternative synthesis entailing the reaction of the lithium salt of 1,4-dimethoxy-1,4-cyclohexadiene with 1,3- bis(iodoethyl)benzene to furnish a bis-alkylated diketone which undergoes acid-catalyzed cyclization to 3,11-diketododecahydrodibenz[a,j]anthracene.

Synthesis of Some Bicyclophanes

Bicyclic aromatic compounds, bicyclophanehexanes of general structure A, have been obtained from sixfold Wittig reactions between aromatic bisphosphonium salts and 1,3,5-benzenetricarbaldehyde.Hydrogenation gave bicyclophanes of structure B.The synthesis of bicyclophanes from ylids prepared from the bisphosphonium salts from 1,3- and 1,4-bis(bromomethyl)benzene, 1,3-bis(bromomethyl)-5-bromobenzene, and 2,5-bis(chloromethyl)thiophene is described and the structures of the bicyclophanes discussed.