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4'-Hydroxyacetophenone

CAS No.99-93-4
Chemical Name:4'-Hydroxyacetophenone
CBNumber:CB7198612
Molecular Formula:C8H8O2
Formula Weight:136.15
MOL File:99-93-4.mol

4'-Hydroxyacetophenone Property

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
Flash point 166 °C
storage temp. Store below +30°C.
solubility methanol: 0.1 g/mL, clear
form Crystalline Powder
pka 8.05(at 25℃)
Specific Gravity 1.109
color Almost white to beige
Odor at 10.00 % in dipropylene glycol. mild sweet hawthorn balsam mimosa
Odor Type floral
Water Solubility 10 g/L (22 ºC)
JECFA Number 2040
BRN 774355
InChIKey TXFPEBPIARQUIG-UHFFFAOYSA-N
LogP 1.35 at 25℃
Substances Added to Food (formerly EAFUS) 4-HYDROXYACETOPHENONE
CAS DataBase Reference 99-93-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII G1L3HT4CMH
NIST Chemistry Reference Acetophenone, 4'-hydroxy-(99-93-4)
EPA Substance Registry System 4-Hydroxyacetophenone (99-93-4)
UNSPSC Code 85151701
NACRES NA.24

Safety

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

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H319-H412
Precautionary statements P264-P273-P280-P305+P351+P338-P337+P313-P501

4'-Hydroxyacetophenone Price More Price(19)

Brand: Sigma-Aldrich(India)
Product number: PHR1971
Product name : Acetaminophen Impurity E
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 100MG
Price: ₹45378.4
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.04311
Product name : 4′-Hydroxyacetophenone
Purity: for synthesis
Packaging: 100G
Price: ₹4660
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 98837
Product name : 4′-Hydroxyacetophenone
Purity: analytical standard
Packaging: 100MG
Price: ₹6365.1
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.04311
Product name : 4′-Hydroxyacetophenone
Purity: for synthesis
Packaging: 250G
Price: ₹9710.01
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 278564
Product name : 4′-Hydroxyacetophenone
Purity: 99%
Packaging: 5G
Price: ₹3236.68
Updated: 2022/06/14
Buy: Buy

4'-Hydroxyacetophenone Chemical Properties,Usage,Production

Chemical Properties almost white to beige crystalline powder
Chemical Properties White to beige powder; sweet, hawthorn, balsam, mimosa aroma
Occurrence Reported found in cloudberry, coffee, cranberry, mango, sherry, and wort.
Uses p-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.
Uses 4?-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
Uses 4′-Hydroxyacetophenone has been used as ketone component in the preparation of 1-aryl-3-phenethylamino-1-propanone hydrochlorides, potential cytotoxic agents, via Mannich reactions.
Application 4'-Hydroxyacetophenone has been suggested for use in perfume compositions as a modifier for the more conventional derivatives of Acetophenonc, etc. mainly in heavy-floral or woodyfloral fragrances where power and low cost arc requested.
Production Methods 4'-Hydroxyacetophenone can be produced 1) from Phenylacetate by heating with Aluminum chloride. 2) from Phenol, Acetylchlonde and Aluminum chloride by Friedel-Craft' reaction.
Preparation Preparation 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°.
Definition ChEBI: A monohydroxyacetophenone carrying a hydroxy substituent at position 4'.
Aroma threshold values Floral 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 Description Pharmaceutical 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 Explosibility Non flammable
Purification Methods Crystallise it from diethyl ether, aqueous EtOH or *benzene/pet ether. [Beilstein 8 H 87, 8 IV 339.]