90909-58-3

Basic information

• Product Name: 2-chloro-6H-benzo[c]chromen-6-one
• CAS NO: 90909-58-3
• Molecular Formula: C₁₃H₇ClO₂
• Molecular Weight: 230.6465
• Mol File: 90909-58-3.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 387.8°C at 760 mmHg
• Flash Point: 210.8°C
• Density: 1.393g/cm³
• Vapor Pressure: 3.2E-06mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2-chloro-6H-benzo[c]chromen-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-6H-benzo[c]chromen-6-one(90909-58-3)
• EPA Substance Registry System: 2-chloro-6H-benzo[c]chromen-6-one(90909-58-3)

Safety Data

• Hazardous Substances Data: 90909-58-3(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 124137-66-2 bis-(2-chloro-6H-benzo[c]chromen-6-yl)-peroxide 
• 108-24-7 acetic anhydride 
• 108990-10-9 2-chloro-6H-benzo[c]benzopyran 
• 16231-67-7 methyl 2'-formyl-[1,1'-biphenyl]-2-carboxylate 
• 106-48-9 4-chloro-phenol 
• 112-36-7 3,6,9-trioxaundecane 
• 309254-39-5 1-bromo-2-{[4-chlorophenyl)oxy]methyl}benzene 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 6373-47-3 2-(benzyloxy)-5-chloroaniline 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 1415717-31-5 2-(2-(allyloxy)-5-chlorophenyl)furan 
• 635-93-8 5-chlorosalicyclaldehyde 

Downstream Products

• 119338-10-2 2-chloro-6,6-diphenyl-6H-benzo[c]chromene 
• 114508-05-3 5-chloro-2-(4-nitro-benzoyloxy)-2'-(4-nitro-benzoyloxymethyl)-biphenyl 

Relevant articles and documents

Cerium Ammonium Nitrate-Mediated Access to Biaryl Lactones: Substrate Scopes and Mechanism Studies

Herein we described an access to biaryl lactones from ortho-aryl benzoic acids via intramolecular O-H/C-H oxidative coupling with the commonly used cerium ammonium nitrate (CAN) as the one-electron oxidant under a thermal condition. The radical interrupting experiment suggested a radical process, while the kinetic isotope effect (KIE) showed that the C-H cleavage likely was not involved in the rate-determining step. Competitive reactions, especially the strikingly different ρ values of Hammett equations, indicated that the reaction rate was more sensitive to the electronic properties on the aryl moiety rather than the carboxylic moiety, which corresponded to the first single electron transfer (SET) step. In addition, the quite negative ρ values (-4.7) of the aryl moiety unveiled the remarkable electrophilic nature of the second intramolecular radical addition process, which was also consistent with product yields and regioselectivity. Moreover, control experiments disclosed that the single electron in the third step was also transferred to CeIV instead of molecular oxygen. Besides, the possible role of co-solvents trifluoroethanol (TFE) and its influences on the CeIV species were discussed. This work elucidated the possible mechanism by proposing the step that had more effects on the total reaction rate and the species that was responsible for the last single electron transfer.

Cerium photocatalyzed dehydrogenative lactonization of 2-arylbenzoic acids

The first cerium photocatalyzed dehydrogenative lactonization of 2-arylbenzoic acids has been developed. This operationally simple protocol allows rapid access to synthetically useful coumarins on gram scale by employing CeCl3 as a photocatalyst and O2 as a terminal oxidant. Overall, this delivers an economical and environmentally amiable entry to diversely substituted coumarins, important structural motifs in bioactive molecules.

Organocatalytic Electrochemical C-H Lactonization of Aromatic Carboxylic Acids

An electrochemical strategy has been developed for radical arene carbon-oxygen bond formation. This reaction utilizes DDQ as a redox mediator, with inexpensive glassy carbon electrodes to facilitate an intramolecular lactonization of biphenyl-2-carboxylic