154418-91-4

Basic information

• Product Name: 9-BROMOTHIENO[2,3-C][1,5]NAPHTHYRIDINE
• Synonyms: 9-BROMOTHIENO[2,3-C][1,5]NAPHTHYRIDINE
• CAS NO: 154418-91-4
• Molecular Formula: C10H5BrN2S
• Molecular Weight: 265.13
• Mol File: 154418-91-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9-BROMOTHIENO[2,3-C][1,5]NAPHTHYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-BROMOTHIENO[2,3-C][1,5]NAPHTHYRIDINE(154418-91-4)
• EPA Substance Registry System: 9-BROMOTHIENO[2,3-C][1,5]NAPHTHYRIDINE(154418-91-4)

Safety Data

• Hazardous Substances Data: 154418-91-4(Hazardous Substances Data)

Upstream product

• 148873-31-8 thieno<2,3-c><1,5>naphthyridine 9-oxide 
• 62506-44-9 thieno<2,3-c><1,5>naphthyridine 

Downstream Products

• 180057-14-1 9-o-Tolyl-thieno[2,3-c][1,5]naphthyridine 5-oxide 
• 180057-12-9 6-Chloro-9-o-tolyl-thieno[2,3-c][1,5]naphthyridine 
• 180057-13-0 9-o-Tolyl-thieno[2,3-c][1,5]naphthyridine 

Relevant articles and documents

On the Bromination of Thieno-fused 1,5-Naphthyridines and their Isomeric N-Oxides Using Dibromoisocyanuric Acid in Fuming Sulfuric Acid

Thieno-1,5-naphthyridine (3), thieno-1,5-naphthyridine 5-oxide (7), thieno-1,5-naphthyridine (5) and thieno-1,5-naphthyridine 5-oxide (9) could conveniently be brominated at room temperature using dibromoisocyanuric acid in fuming sulfuric acid.Bromination occurred in good to moderate yields at the β position in the thiophene ring.Thieno-1,5-naphthyridine 9-oxide (12) and thieno-1,5-naphthyridine 9-oxide (13) also gave substitution in the thiophene ring at 95 deg.It was also found that 12 was deoxygenated under these reaction conditions.Direct oxidation of the brominated thienonaphthyridines with m-chloroperbenzoic acid gave the 5-oxides in high yield.

ON THE BROMINATION OF THE THREE ISOMERIC THIENOFUSED 1,5-NAPHTHYRIDINES AND THEIR 5-N-OXIDES

Thieno-1,5-naphthyridine (1) and its 5-N-oxide (5) were conveniently brominated at room temperature with tetrabutylammonium perbromide in the presence of a large excess of sodium hydrogen carbonate.Compound (1) gave the 1- and 3-bromo derivatives in a 4:1 ratio, while 5 was regioselectively brominated in the 3-position.Thieno-1,5-naphthyridine (7), its 5-N-oxide (11) and thieno-1,5-naphthyridine (14) did not react under these conditions, but gave products in the reaction with bromine in refluxing thionyl chloride.Compound (7) gave the 1-bromo derivative as main product and interestingly the 1,7-dibromo derivative as by-product.The reaction of 11 and 14 with bromine in thionyl chloride gave mainly chlorinated products.