4-Acetylphenol
4'-Hydroxyacetophenone
CAS: 99-93-4
Molecular Formula: C8H8O2
4-Acetylphenol - Names and Identifiers
| Name | 4'-Hydroxyacetophenone |
| Synonyms | 4-Acetylphenol 4-Hydroksyacetofenol 4-Hydroxyacetophenone HYDROXYACETOPHENONE-4 P-Hydroxyacetophenone HYDROXYBENZOPHENONE-4 4'-hydroxy-acetophenon 4′-Hydroxyacetophenone 4'-Hydroxyacetophenone 4'-Hydroxy acetophenone Acetophenone, p-hydroxy- Hydroxyacetophenone, para 1-(4-hydroxyphenyl)-ethanon 1-(4-Hydroxyphenyl)ethanone Ethanone, 1-(4-hydroxyphenyl)- |
| CAS | 99-93-4 |
| EINECS | 202-802-8 |
| InChI | InChI=1/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3 |
| InChIKey | TXFPEBPIARQUIG-UHFFFAOYSA-N |
4-Acetylphenol - Physico-chemical Properties
| Molecular Formula | C8H8O2 |
| Molar Mass | 136.15 |
| Density | 1.109 |
| Melting Point | 132-135°C(lit.) |
| Boling Point | 147-148°C3mm Hg(lit.) |
| Flash Point | 166 °C |
| JECFA Number | 2040 |
| Water Solubility | 10 g/L (22 ºC) |
| Solubility | Soluble in ethanol and ether, slightly soluble in water |
| Vapor Presure | 0.002Pa at 20℃ |
| Appearance | White to off-white (Solid) |
| Specific Gravity | 1.109 |
| Color | Almost white to beige |
| BRN | 774355 |
| pKa | 8.05(at 25℃) |
| Storage Condition | Store below +30°C. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.5577 (estimate) |
| MDL | MFCD00002359 |
| Physical and Chemical Properties | White crystals soluble in hot water, methanol, ether, acetone, insoluble in petroleum ether |
| Use | Raw materials for the manufacture of choleretic drugs and other organic synthesis |
4-Acetylphenol - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | 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 |
| TSCA | Yes |
| HS Code | 29145000 |
| Hazard Note | Irritant |
4-Acetylphenol - Reference
| Reference Show more | 1. Yu Honghong, Gao Xiaoyan. Based on UPLC-Q-TOF/MS ~ E, rapid analysis of chemical constituents in mianyinchen [J]. Central South pharmacy, 2019, v.17;No.160(05):22-27. |
4-Acetylphenol - Reference Information
| FEMA | 4330 | 4-HYDROXYACETOPHENONE |
| LogP | 1.35 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | p-hydroxyacetophenone, because its molecule contains hydroxyl and ketone groups on the benzene ring, therefore, it is often used as an intermediate in organic synthesis to react with other compounds to synthesize many important substances. Generally used for the synthesis of pharmaceutical intermediates (α-bromo-p-hydroxyacetophenone, choleretic drugs, antipyretic analgesics and other drugs), Other (spices, feed, etc.; Pesticides, dyes, liquid crystal materials, etc.). |
| Application | p-hydroxyacetophenone is white needle-like crystal at room temperature, naturally occurring in the stems and leaves of Artemisia scoparia, in the roots of plants such as ginseng baby Vine. It can be used in the manufacture of choleretic drugs and other raw materials for organic synthesis. |
| preparation | a synthesis method of p-hydroxyacetophenone is carried out according to the following steps:(1) esterification reaction: In a 500ml reaction flask, 60g(0.63mol) of phenol and 70.0g(0.68mol) of acetic anhydride are added, stirred, cooled to 10 ℃, and the first drop of concentrated sulfuric acid is added dropwise, after the reaction is reduced to normal temperature, the second drop of concentrated sulfuric acid is added dropwise. The amount of concentrated sulfuric acid added twice is 0.5g, after cooling to 60~70 ℃, the acetic acid was distilled off under reduced pressure, the reaction solution was poured into 3 times the amount of water, adjusted to pH 8~9 with 5% sodium hydroxide, and extracted with ethyl acetate for 3 times, the extracts were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to obtain 84.3g of phenyl acetate liquid, with a yield of 94.6%; Divided into three parts for standby use;(2)Fries rearrangement: take step (1) 27.2g(0.2mol) of the obtained phenyl acetate was placed in a 40.0 mL reaction flask, 30ml of O-dichlorobenzene was added under stirring, and 0.3g (mol) of aluminum trichloride was slowly added below 10 °c, temperature increased to 8 Reaction was carried out at 0 ℃ for 3.5 hours, and the reaction was completed by HPLC; Then it was reduced to 50~60 ℃, and water was slowly added for steam distillation; The distillate was separated into layers to obtain an O-dichlorobenzene layer containing O-hydroxyacetophenone, drying, filtration, for subsequent feeding; Residual liquid and activated carbon while hot filtration, cooling crystallization, filtration, P-hydroxyacetophenone white solid 11.8g, purity 99.3%, yield 43.3%;(3) the first cycle: take 27.2g(0.2mol) of phenyl acetate obtained in step (1), and add the O-dichlorobenzene dry liquid containing O-hydroxyacetophenone obtained in step (2) under stirring, under the condition of lower than 10 ℃, 40.0g(0.3mol) of aluminum trichloride is slowly added, and the mixture is heated to 80 ℃ and reacted for 3.5 hours, and the reaction of all raw materials is finished by HPLC detection; then it is reduced to 50~60 ℃, water is slowly added for steam distillation; The distillate is stratified to obtain an O-dichlorobenzene layer containing O-hydroxyacetophenone, dried and filtered for subsequent feeding; The residual liquid is filtered while hot with activated carbon, concentration, cooling crystallization, filtration, P-hydroxyacetophenone white solid 14.1g, purity 99.6%, yield 51.9%;(4) the second Secondary cycle: the process is the same as that of the first cycle. Take 27.2g (0.2mol) of phenyl acetate obtained in step (1) and add the layered dry liquid of O-dichlorobenzene layer containing O-hydroxyacetophenone after the first cycle to react, P-hydroxyacetophenone white solid 14.8g, purity 99.7%, yield 54.3%;(5) step (2)~(4) three times the white solid reaction is combined, that is, the final product, that is, 40.7g of p-hydroxyacetophenone;(6) step (4) the O-dichlorobenzene layer containing O-hydroxyacetophenone after being separated by steam distillation is extracted twice with 5% sodium hydroxide solution, and then the layers are separated, the aqueous layers were combined and adjusted to pH 3-4 with 10% hydrochloric acid; The aqueous layers were extracted twice with ethyl acetate, combined and dried, filtered and concentrated, and then purified to obtain 14.7g of O-hydroxyacetophenone. |
| purpose | raw materials for the manufacture of cholagogue and other organic synthesis This product is an intermediate of organic synthesis, for the production of spices. P-hydroxyacetophenone is also a choleretic. raw materials of medicine, perfume and organic synthesis as intermediates of organic synthesis, they can be used in the production of perfume. The synthesis of a-bromo-p-hydroxyacetophenone, which is mainly used, is an important intermediate for the synthesis of a selective B l receptor blocker-Atenolol (#1). |
| production method | is derived from the acylation and translocation of phenol. Phenol and acetyl chloride were mixed and heated slowly until the evolution of hydrogen chloride ceased to yield crude phenyl acetate. Nitrobenzene was added thereto, and aluminum trichloride was added under cooling, followed by stirring at room temperature for 2-3 hours. It was then poured into cold water and 1:3 hydrochloric acid was added until clear. Extraction with diethyl ether, recovery of diethyl ether from the extract, followed by steam distillation, nitrobenzene and O-hydroxyacetophenone by-product are distilled off at any time with steam, and p-hydroxyacetophenone remains in the residue. The residue is extracted with diethyl ether, the ether is recovered, and the crude product is obtained by cooling and crystallizing, and the product is recrystallized with water. In the above acylation operation, acetic anhydride can be used instead of acetyl chloride, and phenol and acetic anhydride are heated to reflux for 3H to form phenyl acetate in a yield of about 83%. No solvent may be used for the translocation under the action of anhydrous aluminum trichloride. In addition, P-hydroxyacetophenone can also be obtained by diazotization and hydrolysis of p-aminoacetophenone with sodium nitrite. |
Last Update：2024-04-09 02:00:11
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