491-37-2 Usage
Description
4-Chromanone is a white to light yellow crystal powder that has been utilized in various applications due to its unique chemical properties. It is a compound that has garnered interest in the scientific community for its potential uses and interactions with other substances.
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].
Check Digit Verification of cas no
The CAS Registry Mumber 491-37-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 1 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 491-37:
(5*4)+(4*9)+(3*1)+(2*3)+(1*7)=72
72 % 10 = 2
So 491-37-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-4H,5-6H2
491-37-2Relevant articles and documents
Regioselective iridium(I)-catalysed remote borylation of oxygenated naphthalenes
Hume, Paul,Furkert, Daniel P.,Brimble, Margaret A.
, p. 3771 - 3773 (2012)
We present our investigations into the regioselective borylation and halogenation of polyoxygenated naphthalene systems that are key precursors to dimeric pyranonaphthoquinone natural products. A variety of oxygenated naphthalenes were successfully borylated with pinacolborane in high yield and excellent regioselectivity using [Ir(COD)OMe]2 and di-tert-butylbipyridine (dtbpy). The boronates were also readily transformed into the corresponding halides, opening new avenues for the preparation of advanced Suzuki coupling substrates useful for the synthesis of natural products.
Two-Phase Reactions in Microdroplets without the Use of Phase-Transfer Catalysts
Yan, Xin,Cheng, Heyong,Zare, Richard N.
, p. 3562 - 3565 (2017)
Many important chemical transformations occur in two-phase reactions, which are widely used in chemical, pharmaceutical, and polymer manufacturing. We present an efficient method for performing two-phase reactions in microdroplets sheared by sheath gas without using a phase-transfer catalyst. This avoids disadvantages such as thermal instability, high cost, and, especially, the need to separate and recycle the catalysts. We show that various alcohols can be oxidized to the corresponding aldehydes and ketones within milliseconds in moderate to good yields (50–75 %). The scale-up of the present method was achieved at an isolated rate of 1.2 mg min?1 for the synthesis of 4-nitrobenzylaldehyde from 4-nitrobenzyl alcohol in the presence of sodium hypochlorite. The biphasic nature of this process, which avoids use of a phase-transfer catalyst, greatly enhances synthetic effectiveness.
Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones
Begum, Ayisha F.,Balasubramanian, Kalpattu K.,Shanmugasundaram, Bhagavathy
, (2021/09/13)
3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.
Oxidant-Free Selective Synthesis of Functionalized Chroman-4-ones from ortho -Hydroxyacetophenones under HOAc/DMSO Conditions
Feng, Yuanyuan,Jiang, Tao-Shan,Li, Shuai,Shi, Xu,Wang, Anan
, (2022/02/10)
A metal-free and oxidant-free acid-promoted DMSO activation and subsequent reaction is reported. In this protocol, two molecules of DMSO are activated by HOAc and serve as dual synthons which react with ortho-hydroxyacetophenones, affording 3-(methylthiomethyl)chroman-4-ones in moderate to good yields with high selectivity.
