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4'-Hydroxyacetophenone

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4'-Hydroxyacetophenone Basic information

Product Name:
4'-Hydroxyacetophenone
Synonyms:
  • 1-(4-hydroxyphenyl)-ethanon
  • 4’-hydroxy-acetophenon
  • 4-Hydroksyacetofenol
  • Acetophenone, p-hydroxy-
  • Ethanone, 1-(4-hydroxyphenyl)-
  • Hydroxyacetophenone, para
  • HYDROXYACETOPHENONE-4
  • HYDROXYBENZOPHENONE-4
CAS:
99-93-4
MF:
C8H8O2
MW:
136.15
EINECS:
202-802-8
Product Categories:
  • Pyridines
  • Pharmaceutical intermediates for Choleretic and Salbutamol
  • Aromatic Acetophenones & Derivatives (substituted)
  • Aromatics
  • Miscellaneous Reagents
  • Eczema, medicine and other organic synthesis intermediates
  • Acetophenone Series
  • FINE Chemical & INTERMEDIATES
  • AcetophenoneCarbonyl Compounds
  • C7 to C8
  • Ketones
  • Organic Photoinitiators
  • Polymerization Initiators
  • Carbonyl Compounds
  • VX:15689727968
Mol File:
99-93-4.mol
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4'-Hydroxyacetophenone Chemical Properties

Melting point:
132-135 °C(lit.)
Boiling point:
147-148 °C3 mm Hg(lit.)
Density 
1.109
FEMA 
4330 | 4-HYDROXYACETOPHENONE
refractive index 
1.5577 (estimate)
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
Water Solubility 
10 g/L (22 ºC)
JECFA Number
2040
BRN 
774355
InChIKey
TXFPEBPIARQUIG-UHFFFAOYSA-N
CAS DataBase Reference
99-93-4(CAS DataBase Reference)
NIST Chemistry Reference
Acetophenone, 4'-hydroxy-(99-93-4)
EPA Substance Registry System
4-Hydroxyacetophenone (99-93-4)
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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

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4'-Hydroxyacetophenone Usage And Synthesis

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.

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

Purification Methods

Crystallise it from diethyl ether, aqueous EtOH or *benzene/pet ether. [Beilstein 8 H 87, 8 IV 339.]

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