354529-43-4

Basic information

• Product Name: 3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene
• Synonyms: 3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene
• CAS NO: 354529-43-4
• Molecular Weight: 318.396
• Mol File: 354529-43-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene(354529-43-4)
• EPA Substance Registry System: 3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene(354529-43-4)

Safety Data

• Hazardous Substances Data: 354529-43-4(Hazardous Substances Data)

Upstream product

• 98015-07-7 2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 97511-04-1 2-bromodibenzo[b,d]thiophene 
• 139962-95-1 2-formyl-4-methoxyphenylboronic acid 

Relevant articles and documents

Synthesis of trans-3,4-dihydroxy-3,4-dihydrophenanthro[3,2-b]-[1]benzothiophene, A potentially carcinogenic metabolite of sulfur heterocycle phenanthro[3,2-b][1]benzothiophene

The present study describes the synthesis of trans-3,4-dihydroxy-3,4-dihydrophenanthro[3,2-b][1]benzothiophene (3), which is a potential proximate carcinogen of the environmentally occurring potent carcinogen phenanthro-[3,2-b][1]benzothiophene (1). Three approaches were investigated for the synthesis of 3. In the first approach, the diarylalkene 9, which was prepared by the Wittig reaction of ylide 7 and aldehyde 8, was subjected to an oxidative photocyclization reaction to produce a mixture of compounds from which 5, a synthetic precursor to 3, was obtained only in trace amounts. The major cyclized product was 10. The second approach entailed the Suzuki cross-coupling reaction of 2-(dihydroxyboryl)-5-methoxybenzaldehyde (12) with 3-bromodibenzothiophene (11) to produce 13 in 92% yield. The aldehyde function of 13 was elongated with trimethylsulfonium iodide in the presence of KOH to generate the ethylene oxide 14, which, after methanesulfonic acid treatment, produced a 1 : 1 mixture of 3-methoxyphenanthro[3,2-b][1]benzothiophene (6) and 3-methoxyphenanthro[1,2-b][1]benzothiophene (15). Only the undesired compound 15 could be isolated in pure form by extracting the mixture with hot ethanol, leaving behind a 7 : 3 mixture of 6 and 15. In the third approach, the Wittig reaction of 7 with 2-bromo-5-methoxybenzaldehyde (16) produced 17 predominantly as the Z-isomer in quantitative yield. Cyclodehydrobromination of 17 with KOH-quinoline at elevated temperature produced a mixture from which 6 and 3-methoxyphenanthro[3,4-b][1]benzothiophene (18) were easily separated by column chromatography in 23 and 51% yields, respectively. The intermediate 6 was conveniently processed to 3 following the reaction sequence: methoxy phenol→o-quinone→dihydrodiol. A relatively polar dihydrodiol obtained by similar processing of the mixture of 6 and 15 was identified as 3.