| Identification | More | [Name]
4'-Hydroxyacetophenone | [CAS]
99-93-4 | [Synonyms]
1-(4-HYDROXY-PHENYL)-ETHANONE
4-ACETOPHENOL
4-ACETYLPHENOL
4-BENZOYLPHENOL
4'-HYDROXYACETOPHENONE
4-HYDROXYACETOPHENONE
4-HYDROXYBENZOPHENONE
4-HYDROXYPHENYL METHYL KETONE
(4-HYDROXY-PHENYL)-PHENYL-METHANONE
ACETYLPHENOL
AKOS BBS-00003226
HYDROXYACETOPHENONE-4
HYDROXYBENZOPHENONE-4
P-ACETOPHENOL
P-BENZOYLPHENOL
P-HYDROXYACETOPHENONE
P-HYDROXYBENZOPHENONE
POB
1-(4-hydroxyphenyl)-ethanon
4’-hydroxy-acetophenon | [EINECS(EC#)]
202-802-8 | [Molecular Formula]
C8H8O2 | [MDL Number]
MFCD00002355 | [Molecular Weight]
136.15 | [MOL File]
99-93-4.mol |
| Chemical Properties | Back Directory | [Appearance]
almost white to beige crystalline powder | [Melting point ]
132-135 °C(lit.)
| [Boiling point ]
147-148 °C3 mm Hg(lit.)
| [density ]
1.109 | [vapor pressure ]
0.002Pa at 20℃ | [FEMA ]
4330 | 4-HYDROXYACETOPHENONE | [refractive index ]
1.5577 (estimate) | [Fp ]
166 °C
| [storage temp. ]
Store below +30°C. | [solubility ]
methanol: 0.1 g/mL, clear
| [form ]
Crystalline Powder | [pka]
8.05(at 25℃) | [color ]
Almost white to beige | [Specific Gravity]
1.109 | [Odor]
at 10.00 % in dipropylene glycol. mild sweet hawthorn balsam mimosa | [Odor Type]
floral | [Water Solubility ]
10 g/L (22 ºC) | [Detection Methods]
HPLC | [JECFA Number]
2040 | [BRN ]
774355 | [InChIKey]
TXFPEBPIARQUIG-UHFFFAOYSA-N | [LogP]
1.35 at 25℃ | [CAS DataBase Reference]
99-93-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Acetophenone, 4'-hydroxy-(99-93-4) | [EPA Substance Registry System]
99-93-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S37/39:Wear suitable gloves and eye/face protection .
S24/25:Avoid contact with skin and eyes .
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
PC4959775
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29145000 |
| Hazard Information | Back Directory | [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]
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. | [Definition]
ChEBI: A monohydroxyacetophenone carrying a hydroxy substituent at position 4'. | [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°. | [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. | [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]
Nonflammable | [Purification Methods]
Crystallise it from diethyl ether, aqueous EtOH or *benzene/pet ether. [Beilstein 8 H 87, 8 IV 339.] |
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