4'-Hydroxyacetophenone

4'-Hydroxyacetophenone Basic information
Product Name:4'-Hydroxyacetophenone
Synonyms:1-(4-hydroxyphenyl)-ethanon;Hydroxyacetophenone, para;HYDROXYACETOPHENONE-4;HYDROXYBENZOPHENONE-4;AKOS BBS-00003226;4-ACETOPHENOL;4-BENZOYLPHENOL;4'-HYDROXYACETOPHENONE
CAS:99-93-4
MF:C8H8O2
MW:136.15
EINECS:202-802-8
Product Categories:Pyridines;Pharmaceutical intermediates for Choleretic and Salbutamol;Eczema, medicine and other organic synthesis intermediates;Aromatics;Miscellaneous Reagents;Aromatic Acetophenones & Derivatives (substituted);FINE Chemical & INTERMEDIATES;Acetophenone Series;Carbonyl Compounds;AcetophenoneCarbonyl Compounds;C7 to C8;Ketones;Organic Photoinitiators;Polymerization Initiators;bc0001;99-93-4;1
Mol File:99-93-4.mol
4'-Hydroxyacetophenone Structure
4'-Hydroxyacetophenone Chemical Properties
Melting point 132-135 °C(lit.)
Boiling point 147-148 °C3 mm Hg(lit.)
density 1.109
vapor pressure 0.002Pa at 20℃
refractive index 1.5577 (estimate)
FEMA 4330 | 4-HYDROXYACETOPHENONE
Fp 166 °C
storage temp. Store below +30°C.
solubility methanol: 0.1 g/mL, clear
form Crystalline Powder
pka8.05(at 25℃)
color Almost white to beige
Specific Gravity1.109
Odorat 10.00 % in dipropylene glycol. mild sweet hawthorn balsam mimosa
Odor Typefloral
Water Solubility 10 g/L (22 ºC)
JECFA Number2040
BRN 774355
InChIKeyTXFPEBPIARQUIG-UHFFFAOYSA-N
LogP1.35 at 25℃
CAS DataBase Reference99-93-4(CAS DataBase Reference)
NIST Chemistry ReferenceAcetophenone, 4'-hydroxy-(99-93-4)
EPA Substance Registry System4-Hydroxyacetophenone (99-93-4)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 36/37/38-22
Safety Statements 26-36/37-37/39-24/25-22-36
WGK Germany 3
RTECS PC4959775
Hazard Note Irritant
TSCA Yes
HS Code 29145000
MSDS Information
ProviderLanguage
1-(4-Hydroxyphenyl)ethanone English
SigmaAldrich English
ACROS English
ALFA English
4'-Hydroxyacetophenone Usage And Synthesis
Chemical PropertiesWhite to beige powder; sweet, hawthorn, balsam, mimosa aroma
Chemical Propertiesalmost white to beige crystalline powder
OccurrenceReported found in cloudberry, coffee, cranberry, mango, sherry, and wort.
Uses4?-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
Usesp-Hydroxyacetophenone is widely used in medicine, cosmetics and industrial fields. It is a natural plant extract, which naturally exists in the stems and leaves of the Compositae plant, Artemisia annua, the roots of plants such as Artemisia annua, Rhododendron, and Panax ginseng. It has a good effect on yellow eyes caused by diseases such as hepatitis, and also has a good auxiliary effect on yellow eyes caused by various reasons. Due to its weak molecular activity, high temperature resistance, melting point of 95-97 °C and boiling point of 296 °C, it is widely used in various liquid pharmaceuticals and can prolong the shelf life of other active ingredients under high temperature conditions. It has no harm to human skin and is the safest high-temperature auxiliary active stabilizer in the pharmaceutical industry.
Uses4′-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
DefinitionChEBI: A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.
PreparationPreparation by Fries rearrangement of phenyl acetate with Lewis acids
aluminium chloride
in 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°.









Aroma threshold valuesFloral type, medium strength odor; recommend smelling in a 10.00% solution or less.
Synthesis Reference(s)Tetrahedron Letters, 32, p. 5829, 1991 DOI: 10.1016/S0040-4039(00)93567-6
General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Flammability and ExplosibilityNonflammable
Purification MethodsCrystallise it from diethyl ether, aqueous EtOH or *benzene/pet ether. [Beilstein 8 H 87, 8 IV 339.]
5-CHLORO-3-BROMO-2-HYDROXYACETOPHENONE,97 % 3-Amino-2-hydroxyacetophenone 4'-Amino-2'-hydroxyacetophenone 2',4',6'-Trihydroxyacetophenone monohydrate 4-Methyl-2-Hydroxyacetophenone PARACETAMOL IMP. G (EP): 1-(4-HYDROXYPHENYL)ETHANONEOXIME (4-HYDROXYACETOPHENONE OXIME) w-Bromo-4-Hydroxyacetophenone 5’-Bromo-3’-nitro-2’-hydroxyacetophenone L-PICEIN -hydroxyacetophenone,3' 5'-DIBROMO-2'-HYDROXYACETOPHENONE 9& 2-(2-CHLOROPHENYL)-5'-FLUORO-2'-HYDROXYACETOPHENONE 3,4-Dihydroxyacetophenone 3',5'-DICHLORO-2'-HYDROXYACETOPHENONE, 9 9% Methoxy-2-hydroxyAcetophenone 5-ACETAMIDO-2-HYDROXYACETOPHENONE MM(CRM STANDARD) PARACETAMOL IMP. I (EP): 2-HYDROXYACETOPHENONE MM(CRM STANDARD) 2-bromo-3-nitro-4-hydroxyacetophenone 2-Bromo-4-Hydroxyacetophenone98%

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