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| Names | |
|---|---|
| Preferred IUPAC name 4-Methylphenol | |
| Systematic IUPAC name 4-Methylbenzenol | |
| Other names 4-Cresol p-Cresol 4-Hydroxytoluene p-Cresylic acid 1-Hydroxy-4-methylbenzene | |
| Identifiers | |
| |
3D model (JSmol) | |
| 1305151 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.003.090 |
| EC Number |
|
| 2779 | |
| KEGG |
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| RTECS number |
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| UNII | |
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| Properties | |
| C7H8O | |
| Molar mass | 108.13 |
| Appearance | colorless prismatic crystals |
| Density | 1.0347 g/ml |
| Melting point | 35.5 °C (95.9 °F; 308.6 K) |
| Boiling point | 201.8 °C (395.2 °F; 474.9 K) |
| 2.4 g/100 ml at 40 °C 5.3 g/100 ml at 100 °C | |
| Solubility inethanol | miscible |
| Solubility indiethyl ether | miscible |
| Vapor pressure | 0.11 mmHg (25 °C)[1] |
| −72.1×10−6 cm3/mol | |
Refractive index (nD) | 1.5395 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | May be fatal if swallowed, inhaled, or absorbed through skin. |
| GHS labelling: | |
   | |
| Danger | |
| H201,H311,H314,H351,H370,H372,H373,H401,H412 | |
| P201,P202,P260,P264,P270,P273,P280,P281,P301+P310,P301+P330+P331,P302+P352,P303+P361+P353,P304+P340,P305+P351+P338,P307+P311,P308+P313,P310,P312,P314,P321,P322,P330,P361,P363,P405,P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 86.1 °C (187.0 °F; 359.2 K) |
| Explosive limits | 1.1%–?[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 207 mg/kg (oral, rat, 1969) 1800 mg/kg (oral, rat, 1944) 344 mg/kg (oral, mouse)[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 5 ppm (22 mg/m3) [skin][1] |
REL (Recommended) | TWA 2.3 ppm (10 mg/m3)[1] |
IDLH (Immediate danger) | 250 ppm[1] |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Relatedphenols | o-cresol,m-cresol,phenol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
para-Cresol, also4-methylphenol, is anorganic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative ofphenol and is an isomer ofo-cresol andm-cresol.[3]
Together with many other compounds,p-cresol is conventionally extracted fromcoal tar, the volatilized materials obtained in the roasting ofcoal to producecoke. This residue contains a few percent by weight ofphenol andcresols. Industrially,p-cresol is currently prepared mainly by a two-step route beginning with thesulfonation oftoluene:[4]
Basic hydrolysis of thesulfonate salt gives the sodium salt of the cresol:
Other methods for the production ofp-cresol include chlorination of toluene followed by hydrolysis. In the cymene-cresol process, toluene isalkylated withpropene to givep-cymene, which can be oxidatively dealkylated in a manner similar to thecumene process.[3]
p-Cresol is consumed mainly in the production ofantioxidants, such asbutylated hydroxytoluene (BHT). The monoalkylated derivatives undergo coupling to give an extensive family of diphenol antioxidants. These antioxidants are valued because they are relatively low in toxicity and nonstaining.[3][5][6]
p-Cresol is produced bybacterial fermentation ofprotein in the humanlarge intestine. It is excreted in feces and urine,[7] and is a component of humansweat that attracts femalemosquitoes.[8][9]
p-Cresol is a constituent oftobacco smoke.[10]
p-Cresol is a major component inpig odor.[11] Temporal glands secretion examination showed the presence of phenol andp-cresol duringmusth in maleelephants.[12][13] It is one of the very few compounds to attract theorchid beeEuglossa cyanura and has been used to capture and study the species.[14]p-Cresol is a component found inhorse urine duringestrus that can elicit theFlehmen response.[15]
