99-93-4 Usage
Description
4'-Hydroxyacetophenone, also known as p-Hydroxyacetophenone, is a natural plant extract that can be found in the stems and leaves of the Compositae plant, Artemisia annua, as well as in the roots of plants such as Artemisia annua, Rhododendron, and Panax ginseng. It is characterized by its weak molecular activity, high temperature resistance, melting point of 95-97 °C, and boiling point of 296 °C.
Uses
Used in Pharmaceutical Industry:
4'-Hydroxyacetophenone is used as a high-temperature auxiliary active stabilizer for prolonging the shelf life of other active ingredients under high temperature conditions. It is considered the safest stabilizer in the pharmaceutical industry due to its harmlessness to human skin.
Used in Cosmetics Industry:
4'-Hydroxyacetophenone is used in cosmetics for its beneficial effects on yellow eyes caused by various diseases, such as hepatitis, and for its auxiliary effect on yellow eyes caused by different reasons.
Used in Chemical Synthesis:
4'-Hydroxyacetophenone is used as a ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, which are potential cytotoxic agents, via Mannich reactions. This application is particularly relevant in the development of new pharmaceutical compounds with potential therapeutic effects.
Preparation
Preparation by Fries rearrangement of phenyl acetate with Lewis acidsaluminium chloridein nitrobenzene at 20–25° or at 50–60°in chlorobenzene between 45° and 65°, sealed tube and subjected to high power microwave irradiation for 2 min only (36%) in nitroethane at 60° (44%)in carbon disulfide at 45° (40%)in petroleum ether at 50° (20%) but between 130° and 175° (40–60%)aluminium chloride–sodium chloride mixture at 240–250° (10%) boron trifluoride at 90° (56%) scandium tris(trifluoromethanesulfonate), in nitromethane, at 50° (39%)titanium tetrachloride at 90–100° (34%)ferric chloride at 65° (25%)zinc chloride at 125° (8%) hydrofluoric acid, between 20° and 100° (94%) polyphosphoric acid, between 20° and 100° (69%) (50–53%)(44%)Nafion-XR 500, sulfonic acid type at 100°ZSM-5, in sulfolane, at 180° (28%)H-ZSM-5 at 400° or at 210° (6%) H-Nu-2 at 170° (15%)HY (Si/Al = 3) or fluorided alumina (Al2O3-F; 3 % wt. F), at 400°.
Synthesis Reference(s)
Tetrahedron Letters, 32, p. 5829, 1991 DOI: 10.1016/S0040-4039(00)93567-6
Flammability and Explosibility
Nonflammable
Purification Methods
Crystallise it from diethyl ether, aqueous EtOH or *benzene/pet ether. [Beilstein 8 H 87, 8 IV 339.]
Check Digit Verification of cas no
The CAS Registry Mumber 99-93-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 99-93:
(4*9)+(3*9)+(2*9)+(1*3)=84
84 % 10 = 4
So 99-93-4 is a valid CAS Registry Number.
99-93-4Relevant articles and documents
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Schultz et al.
, p. 3315 (1971)
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Matsuura,Kitaura
, p. 3311 (1967)
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Chemoselective and ligand-free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina-supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst
Das, Asit Kumar,Nandy, Sneha,Bhar, Sanjay
, (2021/05/10)
An economically efficient and operationally simple ligand-free protocol for the chemoselective oxidation of benzylic alcohols to carbonyl compounds has been developed using alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst along with potassium tert-butoxide in the presence of aerial oxygen as an eco-friendly oxidant. The aliphatic alcohols remained unaffected under the present condition. Excellent chemoselectivity has also been demonstrated through intermolecular and intramolecular competition experiments. This protocol accommodates a diverse range of substituents with the tolerance of various sensitive moieties during the reaction. The catalyst could be recovered by filtration and reused consecutively without any significant loss in the catalytic activity. Moreover, the heterogeneity of the catalyst has also been established by the “hot filtration method (Sheldon's test)”.
Aryl phenol compound as well as synthesis method and application thereof
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Paragraph 0237-0240, (2021/05/12)
The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.