3034-04-6

Basic information

• Product Name: 6-METHOXYFLAVANONE
• Synonyms: METHOXYFLAVANONE, 6-;6-METHOXYFLAVANONE;6-METHOXYFLAVANONE 98%;METHOXYFLAVANONE, 6-(P);2-Phenyl-6-methoxy-2,3-dihydro-4H-1-benzopyran-4-one;2-Phenyl-6-methoxy-2H-1-benzopyran-4(3H)-one;2-Phenyl-6-methoxychroman-4-one;6-Methoxyflavanone,98%
• CAS NO: 3034-04-6
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• EINECS: -0
• Product Categories: Flavanones;Biochemistry;Flavonoids
• Mol File: 3034-04-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 141-143 °C(lit.)
• Boiling Point: 425.5°Cat760mmHg
• Flash Point: 202.9°C
• Appearance: /
• Density: 1.199g/cm³
• Vapor Pressure: 1.91E-07mmHg at 25°C
• Refractive Index: 1.587
• BRN: 248912
• CAS DataBase Reference: 6-METHOXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXYFLAVANONE(3034-04-6)
• EPA Substance Registry System: 6-METHOXYFLAVANONE(3034-04-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 3034-04-6(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellowish-green crystalline powder

InChI:InChI=1/C16H14O3/c1-18-12-7-8-15-13(9-12)14(17)10-16(19-15)11-5-3-2-4-6-11/h2-9,16H,10H2,1H3/t16-/m1/s1

Upstream product

• 3033-90-7 (E)-1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 100-52-7 benzaldehyde 
• 22867-46-5 (E)-4-methoxyphenyl cinnamate 
• 26964-24-9 6-methoxyflavone 
• 150-76-5 4-methoxy-phenol 
• 99430-02-1 4-methoxyphenyl 2,3-dibromo-3-phenylpropanoate 
• 102-92-1 Cinnamoyl chloride 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 1101612-92-3 C₂₁H₂₂O₅ 
• 18288-07-8 3-(2-hydroxy-5-methoxyphenyl)-1-phenyl-2-propene-1-one 
• 99430-03-2 2'-hydroxy-5'-methoxychalcone 
• 3262-89-3 triphenylboroxine 
• 59887-88-6 6-methoxy-chromen-4-one 

Downstream Products

• 26964-24-9 6-methoxyflavone 
• 93176-00-2 3-Hydroxy-6-methoxyflavone 
• 3033-90-7 (E)-1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 75595-96-9 (2S,3R)-3-Chloro-6-methoxy-2-phenyl-chroman-4-one 
• 71993-26-5 3,3-Dichloro-6-methoxy-2-phenyl-chroman-4-one 
• 1431952-43-0 3-ferrocenylmethylidenyl-6-methoxy-2-phenylchroman-4-one 
• 76279-00-0 4-oxo-2-phenylchroman-6-yl acetate 
• 1289081-28-2 6-propionoxyflavanone 
• 6665-83-4 6-hydroxyflavone 
• 1228118-69-1 (-)-(S)-6,4'-dihydroxyflavanone 

Relevant articles and documents

Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines

The cationic Ru–H complex [(C6H6)(PCy3)(CO)RuH]+BF4– (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be a highly effective catalyst for the deaminative coupling reaction of 2′-hydroxyaryl ketones with simple amines to form 3-substituted flavanone products. The analogous deaminative coupling reaction of 2-aminobenzamides with branched amines directly formed 3,3-disubstituted quinazolinone products. The catalytic method efficiently installs synthetically useful flavanone and quinazolinone core structures without employing any reactive reagents.

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.