13210-15-6

Basic information

• Product Name: 2-Chloro-9H-xanthen-9-one
• Synonyms: 2-Chloro-9H-xanthen-9-one;2-Chloroxanthone
• CAS NO: 13210-15-6
• Molecular Formula: C₁₃H₇ClO₂
• Molecular Weight: 230.65
• Mol File: 13210-15-6.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 383.5°Cat760mmHg
• Flash Point: 169.7°C
• Appearance: /
• Density: 1.393g/cm³
• Vapor Pressure: 4.39E-06mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2-Chloro-9H-xanthen-9-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-9H-xanthen-9-one(13210-15-6)
• EPA Substance Registry System: 2-Chloro-9H-xanthen-9-one(13210-15-6)

Safety Data

• Hazardous Substances Data: 13210-15-6(Hazardous Substances Data)

Usage

General Description

2-Chloro-9H-xanthen-9-one, also known as xanthen-9-one, 2-chloro- or 9H-xanthen-9-one, 2-chloro, is a chemical compound with the molecular formula C13H8Cl2O2. It is a white to off-white solid with a molecular weight of 269.11 g/mol. 2-Chloro-9H-xanthen-9-one is primarily used as a dye intermediate and in the production of fluorescent dyes and pigments. It is also used in the synthesis of various heterocyclic compounds and pharmaceuticals. 2-Chloro-9H-xanthen-9-one is not known to have any significant commercial or industrial applications beyond its use as a chemical intermediate.

InChI:InChI=1/C13H7ClO2/c14-8-5-6-12-10(7-8)13(15)9-3-1-2-4-11(9)16-12/h1-7H

Upstream product

• 137653-89-5 7-chloro-1,2,3,4-tetrahydro-xanthen-9-one 
• 106-48-9 4-chloro-phenol 
• 69-72-7 salicylic acid 
• 201230-82-2 carbon monoxide 
• 93-67-4 5-chloro-2-phenoxyaniline 
• 2770-11-8 2-(4-chlorophenoxy)aniline 
• 552-89-6 2-nitro-benzaldehyde 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 635-93-8 5-chlorosalicyclaldehyde 
• 50-79-3 2,5-dichlorobenzoic acid 
• 19398-61-9 2,5-dichlorotoluene 
• 120-92-3 cyclopentanone 
• 93467-41-5 6-chloro-2-spiro(cyclopentane)chromanone 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 

Downstream Products

• 92-83-1 xanthene 
• 60085-78-1 Clopipazan 

Relevant articles and documents

Use of pyridine as cocatalyst for the synthesis of 2-carboxy substituted diphenylethers by Ullmann-Goldberg condensation

The synthesis of 2-carboxy-diphenylethers from o-chloro-benzoic acid and phenols is reported using water as solvent and copper, cuprous iodide and pyridine as catalysts.

Microwave-assisted synthesis of xanthones promoted by ytterbium triflate

Xanthones represent a class of naturally occurring compounds with valuable and promising reported pharmacological activities. One of the main disadvantages in the use of such products is related to the difficulties in their chemical synthesis. In this Letter a new and improved method for the chemical synthesis of xanthones is described. The title compounds have been synthesized in good yields under microwave irradiation from substituted 2-hydroxybenzoic acids and phenols in the presence of Yb(OTf)3 hydrate as the catalyst.

Visible-Light-Induced Aerobic Oxidation of Benzylic C(sp 3)-H of Alkylarenes Promoted by DDQ, tert -Butyl Nitrite, and Acetic Acid

A visible-light photocatalytic aerobic oxidation of benzylic C(sp 3)-H bonds proceeded in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tert -butyl nitrite, and acetic acid. Advantages of this aerobic oxidation method include its relatively mild conditions, the use of visible-light irradiation instead of conventional thermal methods, the use of a low catalyst loading, and the ability to oxidize a range of alkylarenes, including xanthenes, thioxanthenes, and 9,10-dihydroacridines, to the corresponding ketones in excellent yields.

Synthesis of xanthones through the palladium-catalyzed carbonylation/C-H activation sequence

A series of xanthones with the dibenzo-γ-pyrone framework were synthesized through the palladium-catalyzed carbonylation/C-H activation sequence from the ortho diazonium salts of diaryl ethers in moderate to excellent yields. After screening the reaction condition, the optimal condition was 5 mol % tetrakis (triphenylphosphine) palladium (0) as the catalyst, potassium carbonate as the base, and toluene as the solvent in the presence of catalytic amount of tetrabutyl ammonium bromide under carbon monoxide atmosphere.

Synthesis of xanthones from 4-(2-phenoxyphenyl)-1-tosyl-1H-1,2,3-triazole via rhodium-catalyzed annulation/oxidation

A series of xanthone derivatives were synthesized by rhodium-catalyzed cycloaddition and sequential oxidation. The derivatives synthesized for excellent yields, including electron-withdrawing and electron-donating substituents, demonstrated the wide applicability of the proposed approach. The xanthones synthesized with different substituent electron effects may go through the same intermediate via two cycloadditions. It is highlighted that the protocol was exemplified by its successful integration into a one-pot synthesis directly from 1-ethynyl-2-phenoxybenzene. We believe that the current method may be an attractive option for the synthesis of xanthone and its derivatives.

Ultraviolet-light-induced aerobic oxidation of benzylic C(sp3)-H of alkylarenes under catalyst- and additive-free conditions

A mild and efficient system has been discovered for the synthesis of α-aryl carbonyl compounds via oxidation of benzylic C–H to C[dbnd]O bonds. This ultraviolet-light-mediated oxygenation reaction exhibited excellent substrate scope including various xanthenes, thioxanthenes and 9, 10-dihydroacridines and afforded the corresponding ketones with good to excellent yields under catalyst- and additive-free conditions at room temperature.