2233-88-7

Basic information

• Product Name: Smoke Yellow
• Synonyms: Smoke Yellow;9,10-Bis(phenylamino)anthracene;C.I.61900;Lumogen L Yellow;N,N'-Diphenyl-9,10-anthracenediamine
• CAS NO: 2233-88-7
• Molecular Formula: C₂₆H₂₀N₂
• Molecular Weight: 0
• Mol File: 2233-88-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Smoke Yellow(CAS DataBase Reference)
• NIST Chemistry Reference: Smoke Yellow(2233-88-7)
• EPA Substance Registry System: Smoke Yellow(2233-88-7)

Safety Data

• Hazardous Substances Data: 2233-88-7(Hazardous Substances Data)

Upstream product

• 598-30-1 sec.-butyllithium 
• 32347-03-8 N-(2-bromobenzylidene)aniline 
• 594-19-4 tert.-butyl lithium 
• 13460-50-9 metaboric acid 
• 84-65-1 9,10-phenanthrenequinone 
• 62-53-3 aniline 
• 10273-79-7 9,10-bis-(α-bromo-benzyl)-anthracene 
• 34863-09-7 N,N'-diphenylanthroquinonediimine 
• 10303-96-5 9,10-bis(formamido)anthracene 

Downstream Products

• 115388-35-7 N,N'-bis-(3-chloro-phenyl)-anthracene-9,10-diyldiamine 
• 720669-49-8 N,N'-di-o-tolyl-anthracene-9,10-diyldiamine 
• 103281-00-1 N,N'-bis-(2-methoxy-phenyl)-anthracene-9,10-diyldiamine 

Relevant articles and documents

Lithium–Bromide Exchange versus Nucleophilic Addition of Schiff's base: Unprecedented Tandem Cyclisation Pathways

By exploring lithium–bromide exchange reactivity of aromatic Schiff's bases with tert-butyllithium (tBuLi), we have revealed unprecedented competitive intermolecular and intramolecular cascade annulation pathways, leading to valuable compounds, such as iso-indolinones and N-substituted anthracene derivatives. A series of reaction parameters were probed, including solvent, stoichiometry, sterics and organolithium reagent choice, in order to understand the influences that limit such ring-closing pathways. With two viable reactivity options for the organolithium on the imine; namely, nucleophilic addition or lithium–bromide exchange, a surprising competitive nature was observed, where nucleophilic addition dominated, even under cryogenic conditions. Considering the most commonly used solvents for lithium–bromide exchange, tetrahydrofuran (THF) and diethyl ether (Et2O), contrasting reactivity outcomes were revealed with nucleophilic addition promoted in THF, while Et2O yielded almost double the conversion of cyclic products than in THF.