67949-59-1

Basic information

• Product Name: Azulene, 1-fluoro- (9CI)
• Synonyms: Azulene, 1-fluoro- (9CI)
• CAS NO: 67949-59-1
• Molecular Formula: C₁₀H₇F
• Molecular Weight: 146.1609832
• Product Categories: HALIDE
• Mol File: 67949-59-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Azulene, 1-fluoro- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Azulene, 1-fluoro- (9CI)(67949-59-1)
• EPA Substance Registry System: Azulene, 1-fluoro- (9CI)(67949-59-1)

Safety Data

• Hazardous Substances Data: 67949-59-1(Hazardous Substances Data)

Usage

General Description

Azulene, 1-fluoro- (9CI) is a chemical compound that belongs to the azulene class of organic compounds. It is a halogenated derivative of azulene, which is a bicyclic aromatic hydrocarbon. The 1-fluoro- derivative of azulene has a fluorine atom attached at the 1-position of the azulene ring. Azulene, 1-fluoro- (9CI) has potential industrial and scientific applications, as well as potential biological activities. It is important to handle this chemical with caution, as it may have hazardous properties and should be used in accordance with safety guidelines and regulations.

Upstream product

• 275-51-4 azulene 
• 14659-03-1 azulene-1-carboxylic acid methyl ester 
• 180129-06-0 3-Fluoro-azulene-1-carboxylic acid 
• 163807-87-2 methyl 3-fluoroazulene-1-carboxylate 

Downstream Products

• 180129-05-9 3-fluoro-1-formylazulene 
• 180129-02-6 1-fluoro-3-methylazulene 
• 161126-13-2 3-bromo-1,7-azulenequinone 
• 161126-12-1 3-bromo-1,5-azulenequinone 

Relevant articles and documents

Facile one-pot fluorination of polycyclic aromatic hydrocarbons (PAHs) with N-fluoro-2,4-dinitroimidazole; scope and limitation

The synthetic utility of N-fluoro-2,4-dinitro-imidazole NF-2,4-DNT, a recently introduced NF fluorinating agent, has been tested for direct one-pot fluorination of several classes of polycyclic aromatic hydrocarbons, PAHs, namely pyrene, crowded alkyl(cycloalkyl)-pyrenes; hexahydro-and tetrahydro-pyrene; benzo[a]anthracene; benzo[a]-and benzo[e] pyrene; perylene; 2,7-di-tert-butylphenanthrene;chrysene; 9-imethylanthracene and anthracene, as well as trans-15:16-dimethyl-dihydropyrene: azulene[2-a]lacenaphthylene and azulene. Although the isolated yields are modest, the ease of handling of the reagent, simple operation (reflux in dichloroethane for 3 days) and the use of 1.1 equivalent of the reagent makes the procedure quite attractive for polynuclear aromatics, avoiding multi-step operations (NO2-PAH → NH2-PAH → N2+-PAH → F-PAH) or the use of toxic or costly reagents (CF3OF, XeF2, etc.); it provides direct one-pot access to a variety of F-PAHs that are not readily made using: other fluorinating agents.

Synthesis and Properties of Fluoroazulenes. II. Electrophilic Fluorination of Azulenes with N-Fluoro Reagents

1-Fluoro- and 1,3-difluoroazulenes were synthesized for the first time by the electrophilic fluorination of azulenes with N-fluoro reagents. Selective preparation of 1-fluoroazulenes were performed by the fluorination of methyl azulene-1-carboxylates, followed by demethoxycarbonylation in 100% H3PO4 2-Substituted azulenes were fluorinated in higher yields. In the 1HNMR of 1-fluoroazulene, long-range .JFH values were not observed at H-2 and H-8, in contrast to those for 1-fluoronaphthalene. The 1-fluorine atom causes significant bathochromic shifts in the visible absorption of azulene, due to the so-called +Iπ effect.