7206-61-3

Basic information

• Product Name: Azulene-1-carboxaldehyde
• Synonyms: Azulene-1-carboxaldehyde
• CAS NO: 7206-61-3
• Molecular Formula: C₁₁H₈O
• Molecular Weight: 156.18062
• EINECS: -0
• Mol File: 7206-61-3.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Azulene-1-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Azulene-1-carboxaldehyde(7206-61-3)
• EPA Substance Registry System: Azulene-1-carboxaldehyde(7206-61-3)

Safety Data

• Hazardous Substances Data: 7206-61-3(Hazardous Substances Data)

Upstream product

• 275-51-4 azulene 
• 67-66-3 chloroform 
• 68-12-2 N,N-dimethyl-formamide 
• 10025-87-3 trichlorophosphate 
• 929021-09-0 C₁₉H₁₂F₆N₂O₄S₂ 
• 110-86-1 pyridine 
• 874-80-6 1-butylpyridinium bromide 
• 149-73-5 trimethyl orthoformate 
• 854154-96-4 [1-Azulen-1-yl-meth-(E)-ylidene]-p-tolyl-amine 
• 769-31-3 1-methylazulene 
• 93187-51-0 1-(dimethylaminomethyl)azulene 

Downstream Products

• 120221-75-2 azulene-1-carbonyl chloride 
• 1022916-41-1 (3Z)-3-(((4Z,6Z,8E)-azulen-1-yl)methylene)-5-phenylindolin-2-one 
• 1022916-50-2 (E)-3-(azulen-1-ylmethylene)-5-methoxyindolin-2-one 
• 1022916-51-3 (3Z)-3-(((4Z,6Z,8E)-azulen-1-yl)methylene)-5-methoxyindolin-2-one 
• 119887-31-9 3-(4-amino-3,5-dimethylphenyl)azulene-1-carbaldehyde 
• 180129-02-6 1-fluoro-3-methylazulene 
• 16458-55-2 di(1-azulenyl)phenylmethane 
• 275-51-4 azulene 

Relevant articles and documents

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Adj-diazuliporphyrins, a new family of dicarbaporphyrinoids with unprecedented mesoionic characteristics

A diazulenylmethane dialdehyde reacted with dipyrrylmethanes in the presence of HCl or HBr, followed by oxidation with FeCl3, to give aromatic adj-diazuliporphyrins. The free base structures must exist as mesoionic species, although these porphyrinoids were isolated as salts of the monoprotonated macrocycles. Reaction with Pd(OAc)2 gave an unprecedented zwitterionic palladium(II) complex that was characterized by X-ray crystallography.

Expansion of Azulenes as Nonbenzenoid Aromatic Compounds for C-H Activation: Rhodium- And Iridium-Catalyzed Oxidative Cyclization of Azulene Carboxylic Acids with Alkynes for the Synthesis of Azulenolactones and Benzoazulenes

Rhodium-catalyzed oxidative [4 + 2] cyclization reactions through the C-H activation of azulene carboxylic acids as nonbenzenoid aromatic compounds with symmetrical and unsymmetrical alkynes were developed under aerobic conditions, which produced azulenolactone derivatives with a wide substrate scope and excellent functional group tolerance. Interestingly, azulenic acids in reaction with alkynes underwent iridium-catalyzed [2 + 2 + 2] cyclization accompanied by decarboxylation to afford tetra(aryl)-substituted benzoazulene derivatives. The reactivity order for C-H activation reaction is greater toward azulene-6-carboxylic acid, azulene-1-carboxylic acid, and azulene-2-carboxylic acid. For the first time, the expansion of azulenes having directing group as nonbenzenoid aromatic compounds for C-H activation was successful, indicating that nonbenzenoid aromatic compounds can be used as good substrates for the C-H activation reaction. Therefore, the research area of C-H activation will certainly expand to nonbenzenoid aromatic compounds in future.

Gold-Catalyzed Direct Alkynylation of Azulenes

A novel catalytic method for the direct C-H alkynylation of azulenes is developed. The gold catalyzed functionalization of this special carbacycle is achieved with hypervalent iodonium reagent TIPS-EBX under mild reaction conditions. With the aid of the developed procedure, several TIPS alkynylated azulene derivatives were synthesized bearing important functional groups for further functionalization.