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

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

Uses

Used in Enzyme Research:
4-Chromanone is used as a substrate in the study of enzyme specificity and catalytic ability for 4-hydroxyacetophenone monooxygenase, which is isolated from Pseudomonas fluorescens ACB. This application helps researchers understand the enzyme's function and its potential role in various biological processes.
Used in Pharmaceutical Industry:
4-Chromanone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for creating new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
4-Chromanone is used as a starting material or intermediate in the synthesis of various organic compounds. Its reactivity and structural properties make it a valuable component in the development of new chemical entities for a range of applications, including materials science, agrochemicals, and specialty chemicals.
Used in Analytical Chemistry:
4-Chromanone can be used as a reference compound or standard in analytical chemistry for the calibration of instruments and the development of new analytical methods. Its distinct properties make it suitable for validating the performance of analytical techniques and ensuring accurate measurements in various fields.

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

• 7170-38-9 3-phenoxypropanoic acid 
• 3055-86-5 3-phenoxypropionitrile 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 4143-72-0 1-(2-hydroxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 84634-64-0 1-(2-hydroxy-phenyl)-3-(4-nitro-phenyl)-propane-1,3-dione 
• 5067-22-1 1-(2-hydroxyphenyl)-3-(4-methylphenyl)propane-1,3-dione 
• 65599-34-0 1-(4-chloro-phenyl)-3-(2-hydroxy-phenyl)-propane-1,3-dione 
• 108-86-1 bromobenzene 
• 42327-53-7 chrom-3-en-4-ol acetate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 30518-51-5 4-chloro-2H-chromene 
• 122-97-4 3-Phenyl-1-propanol 

Downstream Products

• 80554-37-6 3-[(E)-piperonylidene-chroman-4-one 
• 21776-95-4 4-ethyl-2H-chromene 
• 101726-79-8 3-[(2-chlorophenyl)methylene]-2,3-dihydro-4H-1-benzopyran-4-one 
• 107519-73-3 3-(m-nitrobenzylidene)-4-chromanone 
• 30779-90-9 (E)-3-benzylidenechroman-4-one 
• 24513-65-3 3-benzylidene-chroman-4-one 
• 30779-94-3 (E)-3-(4-methoxybenzylidene)chroman-4-one 
• 130688-83-4 (E)-3-(2-hydroxybenzylidene)chroman-4-one 
• 101278-08-4 3-benzoyl-chroman-4-one 
• 132794-01-5 (E)-3-(4-hydroxy-3-methoxybenzylidene)chroman-4-one 
• 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 

Relevant articles and documents

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