491-37-2

Basic information

• Product Name: 4-Chromanone
• Synonyms: ,3-Dihydro-2-benzopyran-4-one;,3-Dihydro-4-benzopyranone;2,3-dihydro-4-benzopyranone;2,3-dihydro-4h-1-benzopyran-4-on;2,3-Dihydro-4H-1-benzopyran-4-one;4-chormanone;Isochromanone;CHROMANONE
• CAS NO: 491-37-2
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• EINECS: 207-736-3
• Product Categories: Fused Ring Systems
• Mol File: 491-37-2.mol
• Article Data: 111

Chemical Properties

• Melting Point: 35-38 °C(lit.)
• Boiling Point: 127-128 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to yellow/Crystalline Powder, Crystals or Low Melting Mass
• Density: 1.1291
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: n20/D 1.575(lit.)
• Storage Temp.: 0-10°C
• Water Solubility: Slightly soluble in water.
• BRN: 124652
• CAS DataBase Reference: 4-Chromanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chromanone(491-37-2)
• EPA Substance Registry System: 4-Chromanone(491-37-2)

Safety Data

• Hazard Codes: Xi
• Statements: 33-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 2
• RTECS: DJ2981225
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 491-37-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

4-Chromanone has been used to study the substrate specificity and catalytic ability of 4-hydroxyacetophenone monooxygenase isolated from Pseudomonas fluorescens ACB

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 5160, 1983 DOI: 10.1021/jo00174a003

Purification Methods

It has been recrystallised from pet ether, or purified by dissolving in *C6H6 washing with H2O, drying (MgSO4), evaporating and distilling in a vacuum, then recrystallising the residue. The liquid has a pleasant lemon-like odour. The semicarbazone has m 227o. [Loudon & Razdan J Chem Soc 4299 1954.] The oxime is prepared from 3g of chromanone, 3g NH2OH.HCl in EtOH (50mL), 6g K2CO3 and refluxed on a water bath for 6hours. The solution is poured into H2O, the solid is filtered off, dried and dissolved in hot *C6H6 which on addition of pet ether yields the oxime as glistening needles m 140o. Hydrolysis of this gives very pure chromanone. The benzal derivative is prepared from 3g of chromanone and 4g PhCHO in 50mL EtOH, heated to boiling, 10mL of conc HCl are added dropwise and set aside for several days. The derivative separates and is recrystallised from EtOH to give yellow needles, m 112o [Powell J Am Chem Soc 45 2711 1923]. Reaction with Pb(OAc)4 yields the 3-acetoxy derivative m 74o (from pet ether + trace of EtOAc) [Cavill et al. J Chem Soc 4573 1954, Beilstein 17/10V 14].

InChI:InChI=1/C9H8O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-4H,5-6H2

Upstream product

• 3055-86-5 3-phenoxypropionitrile 
• 67-56-1 methanol 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 117543-28-9 1-chloro-3-phenyloxy-1-propyne 
• 180469-87-8 (-)-(3R,4S)-Epoxychromane 
• 108-95-2 phenol 
• 13610-02-1 1-phenoxy-2-propyne 
• 254-04-6 2H-chromene 
• 166983-61-5 HI-D₁₂ 
• 123-63-7 paracetaldehyde 
• 7664-93-9 sulfuric acid 
• 75-07-0 acetaldehyde 
• 1481-93-2 4-hydroxychroman 
• 108-86-1 bromobenzene 

Downstream Products

• 130688-86-7 (3E)-2,3-dihydro-3-[(3,4-dimethoxyphenyl)methylene]-4H-1-benzopyran-4-one 
• 71972-51-5 (E)-3-(3-hydroxybenzylidene)chroman-4-one 
• 225-55-8 6H-<1> benzopyranno <4,3-b> quinoleine 
• 71972-47-9 (E)-3-(3-methoxybenzylidene)chroman-4-one 
• 100969-02-6 chroman-4-one phenylhydrazone 
• 61661-19-6 3-(4'-N,N-dimethylaminobenzylidenyl)-2,3-dihydro-4H-1-benzopyran-4-one 
• 16982-86-8 3-methyl-chroman-4-one 
• 491-38-3 1-benzopyran-4(4H)-one 
• 6968-35-0 7-hydroxy-indan-1-one 
• 19847-26-8 3-(2-hydroxy-phenoxy)-propionic acid 
• 21776-95-4 4-ethyl-2H-chromene 
• 71972-49-1 3-(3-benzyloxy-4-methoxybenzylidene)-2,3-dihydro-4H-1-benzopyran-4-one 
• 171015-59-1 3-(4-benzyloxy-3-methoxybenzylidene)-2,3-dihydro-4H-1-benzopyran-4-one 
• 22362-59-0 1-(2-hydroxyphenyl)heptan-1-one 

Relevant articles and documents

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Two-Phase Reactions in Microdroplets without the Use of Phase-Transfer Catalysts

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Oxidant-Free Selective Synthesis of Functionalized Chroman-4-ones from ortho -Hydroxyacetophenones under HOAc/DMSO Conditions

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