22190-65-4

Basic information

• Product Name: [3,8-Dimethyl-5-(1-methylethyl)-1-azulenyl]phenylmethanone
• Synonyms: [3,8-Dimethyl-5-(1-methylethyl)-1-azulenyl]phenylmethanone;3-Benzoylguaiazulene
• CAS NO: 22190-65-4
• Molecular Formula: C₂₂H₂₂O
• Molecular Weight: 0
• Mol File: 22190-65-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [3,8-Dimethyl-5-(1-methylethyl)-1-azulenyl]phenylmethanone(CAS DataBase Reference)
• NIST Chemistry Reference: [3,8-Dimethyl-5-(1-methylethyl)-1-azulenyl]phenylmethanone(22190-65-4)
• EPA Substance Registry System: [3,8-Dimethyl-5-(1-methylethyl)-1-azulenyl]phenylmethanone(22190-65-4)

Safety Data

• Hazardous Substances Data: 22190-65-4(Hazardous Substances Data)

Upstream product

• 489-84-9 7-isopropyl-1,4-dimethyl-azulene 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 22195-75-1 3-Tropylguaiazulen 
• 102560-55-4 (5-isopropyl-3,8-dimethyl-azulen-1-yl)-phenyl-acetonitrile 

Downstream Products

• 39665-57-1 2-Benzylguajazulen 
• 39711-52-9 1-Benzoyl-7-isopropyl-3,4-dimethylazulen 
• 39665-56-0 2-Benzoylguajazulen 
• 1251734-93-6 1-{3-[(3-benzoyl-7-isopropyl-4-methylazulen-1-yl)carbonyl]-7-isopropyl-4-methylazulen-1-yl}ethanone 

Relevant articles and documents

Spontaneous substitution of azulene-derived benzylic alcohols by thiols and its application to labeling/protection of biothiols

By mixing guaiazulene-3-methanol derivatives and thiols at room temperature, benzylic substitution of the alcohol proceeded to yield the corresponding sulfide. Because of the blue color of the guaiazulene derivative, this spontaneous reaction was used for labeling of paper-immobilized biothiols. By treatment with tris(2-carboxyethyl)phosphine hydrochloride, the guaiazulene-3-ylmethyl part of the sulfide could be removed and the original thiol recovered. Based on these findings, a guaiazulene-3-methanol derivative was used as a protective group for the synthesis of cysteine derivatives.

Synthesis of Azulen-1-yl Ketones via Oxidative Cleavage of C-C Multiple Bonds in N-Sulfonyl Enamides and 1-Alkynes under Air and Natural Sunlight

A synthetic method to prepare azulen-1-yl ketones was developed via oxidative cleavage of the C-C double bond in the reaction of easily obtainable N-sulfonyl enamides with Cs2CO3 under air and natural sunlight and in the absence of a photosensitizer. Oxidative cleavage of C-C triple bonds was also demonstrated for the synthesis of azulen-1-yl ketones via a tandem Cu-catalyzed [3 + 2] cycloaddition, Rh-catalyzed arylation, photooxygenation, and ring-opening reaction in one pot under air and natural sunlight.