118-93-4 Usage
Description
2'-Hydroxyacetophenone is a phenolic compound characterized by its clear yellow to brown liquid appearance and a sweet, heavy floral, herbaceous odor reminiscent of mown hay or hawthorn. It is known for its naphthyl, cinnamon, cherry pit, coumarin, phenolic, tobacco, and honey taste characteristics at 5.0 ppm. This chemical is found in various natural sources such as beef, cassia oil, cocoa, coffee, Jamaican rum, tomato, Scotch whiskey, sherry, tea, mountain papaya, roasted almond, and black choke berry. It serves as a pharmaceutical secondary standard for quality control in pharmaceutical laboratories and manufacturers, offering a convenient and cost-effective alternative to in-house working standards.
Uses
Used in Pharmaceutical Industry:
2'-Hydroxyacetophenone is used as a pharmaceutical intermediate, playing a crucial role in the synthesis of various pharmaceutical compounds.
Used in Organic Synthesis:
This chemical is used as an intermediate or raw material in organic synthesis, particularly for preparing a Schiff’s base al-alkoxide initiator that facilitates the controlled polymerization of DL-lactide.
Used in Flavor and Fragrance Industry:
Used in Anti-myobacterial and Anticancer Agents:
2'-Hydroxyacetophenone is a phenolic compound used in the synthesis of potential anti-myobacterial and anticancer agents, contributing to the development of new treatments for various diseases.
Used in Taste Modifying Compositions:
This chemical has been employed as the effective component in balsamic compounds for fabricating taste modifying compositions, enhancing the sensory experience of food and beverages.
Used in the Synthesis of 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran:
2'-Hydroxyacetophenone is used in the reaction with benzoyl chloride to generate 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran, which exhibits good performance for treating cancer and other proliferative diseases such as psoriasis and restenosis.
Reference
Bhaw-Luximon, A.; Jhurry, D.; Spassky, N., Controlled polymerization of DL-lactide using a Schiff's base al-alkoxide initiator derived from 2-hydroxyacetophenone. Polym. Bull. 2000, 44, 31-38.
Johann Wonschick; Clemens M. Putter; Keepe, E., TASTE MODIFYING COMPOSITIONS PCT WO 2016/103183 A1 2016.
Alexander J Bridges; Saltiel, A. R., 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders US Patent US5525625 1996.
Preparation
Preparation by Fries rearrangement of phenyl acetate, with Lewis acidsaluminium chloride.
Synthesis Reference(s)
Tetrahedron Letters, 24, p. 377, 1983 DOI: 10.1016/S0040-4039(00)81412-4
Check Digit Verification of cas no
The CAS Registry Mumber 118-93-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 8 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 118-93:
(5*1)+(4*1)+(3*8)+(2*9)+(1*3)=54
54 % 10 = 4
So 118-93-4 is a valid CAS Registry Number.
118-93-4Relevant articles and documents
Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization
Kathe, Prasad M.,Berkefeld, Andreas,Fleischer, Ivana
supporting information, p. 1629 - 1632 (2021/02/09)
This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.
Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system
Dandia, Anshu,Saini, Pratibha,Chithra,Vennapusa, Sivaranjana Reddy,Parewa, Vijay
, (2021/03/15)
An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.
Visible-Light-Driven Selective Air-Oxygenation of C?H Bond via CeCl3 Catalysis in Water
Xie, Pan,Xue, Cheng,Shi, Sanshan,Du, Dongdong
, p. 2689 - 2693 (2021/05/07)
Visible-light-induced C?H aerobic oxidation is an important chemical transformation that can be applied for the synthesis of aromatic ketones. High-cost catalysts and toxic solvents were generally needed in the present methodologies. Here, an efficient aqueous C?H aerobic oxidation protocol was reported. Through CeCl3-mediated photocatalysis, a series of aromatic ketones were produced in moderate to excellent yields. With air as the oxidant, this reaction could be performed under mild conditions in water and demonstrated high activity and functional group tolerance. This method is economical, highly efficient, and environmentally friendly, and it will provide inspiration for the development of aqueous photochemical synthesis reactions.