13178-98-8

Basic information

• Product Name: 3-chloro-2-phenyl-4H-chromen-4-one
• Synonyms: 3-chloro-2-phenyl-4H-chromen-4-one
• CAS NO: 13178-98-8
• Molecular Formula: C₁₅H₉ClO₂
• Molecular Weight: 256.68376
• Mol File: 13178-98-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-chloro-2-phenyl-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-2-phenyl-4H-chromen-4-one(13178-98-8)
• EPA Substance Registry System: 3-chloro-2-phenyl-4H-chromen-4-one(13178-98-8)

Safety Data

• Hazardous Substances Data: 13178-98-8(Hazardous Substances Data)

Upstream product

• 245322-93-4 1-(2-methoxyphenyl)-3-phenylprop-2-yn-1-ol 
• 135-02-4 ortho-anisaldehyde 
• 536-74-3 phenylacetylene 
• 89-95-2 2-methyl-benzyl alcohol 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 16619-66-2 1-(2-methoxyphenyl)-3-phenylprop-2-yn-1-one 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 525-82-6 FLAVONE 
• 56-23-5 tetrachloromethane 
• 4578-66-9 o-benzoyloxybenzoic acid 

Downstream Products

• 525-82-6 FLAVONE 
• 2030-45-7 2-benzoylbenzofuran-3(2H)-one 

Relevant articles and documents

A facile preparation of 3-haloflavones using hypervalent iodine* chemistry

Various 3-haloflavones were prepared by the reaction of the corresponding flavone derivatives with iodobenzene diacetate and trimethylsilyl halide under mild reaction conditions. The iodobenzene diacetate could be replaced by the polymer-supported iodoben

Synthesis of 3-halogenated flavonoids via electrophile-promoted cyclization of 2-(3-aryl-2-propynoyl)anisoles

Treatment of 2-(1-aryl-3-propynoyl) anisoles 1 with N-chlorosuccinimide (NCS) or N-bromosuccinimide (NBS) gave the 3-halogenated flavones and their related molecules in moderate yields.

Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists

A broad screening of phytochemicals has demonstrated that certain flavone and flavonol derivatives have a relatively high affinity at A3 adenosine receptors, with K(i) values of ≥1 μM (Ji et al. J. Med. Chem. 1996, 39, 781-788). We have further modified the flavone structure to achieve a degree of selectivity for cloned human brain A3 receptors, determined in competitive binding assays versus [125I]AB-MECA [N6-(4-amino-3- iodebenzyl)adenosine-5'-(N-methyluronamide)]. Affinity was determined in radioligand binding assays at rat brain A1 and A(2A) receptors using [3H]- N6-PIA ([3H]-(R)-N6-phenylisopropyladenosine) and [3H]CGS21680 [[3H]-2- [[4-(2-carboxyethyl)phenyl]ethylamino]-5'-(N-ethylcarbamoyl)adenosine], respectively. The triethyl and tripropyl ether derivatives of the flavonol galangin, 4, had K(i) values of 0.3-0.4 μM at human A3 receptors. The presence of a 5-hydroxyl group increased selectivity of flavonols for human A3 receptors. The 2',3,4',7-tetraethyl ether derivative of the flavonol morin, 7, displayed a K(i) value of 4.8 μM at human A3 receptors and was inactive at rat A1/A(2A) receptors. 3,6-Dichloro-2'-(isopropyloxy)-4'- methylflavone, 11e, was both potent and highly selective (~200-fold) for human A3 receptors (K(i) = 0.56 μM). Among dihydroflavonol analogues, the 2-styryl instead of the 2-aryl substituent, in 15, afforded selectivity for human A3 vs rat A1 or A(2A) receptors. The 2-styryl-6-propoxy derivative, 20, of the furanochromone visnagin was 30-fold selective for human A3 receptors vs either rat A1 or A(2A) receptors. Several of the more potent derivatives effectively antagonized the effects of an agonist in a functional A3 receptor assay, i.e. inhibition of adenylyl cyclase in CHO cells expressing cloned rat A3 receptors. In conclusion, these series of flavonoids provide leads for the development of novel potent and subtype selective A3 antagonists.