p-Cresol

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p-Cresol
Skeletal formula of p-cresol
Skeletal formula of p-cresol
3D model of p-cresol
3D model of p-cresol
File:P-Cresol.jpg
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
DrugBank
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EC Number
  • 203-398-6
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
2779
KEGG
RTECS number
  • GO6475000
UNII
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  • InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 checkY
    Key: IWDCLRJOBJJRNH-UHFFFAOYSA-N checkY
  • InChI=1/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
    Key: IWDCLRJOBJJRNH-UHFFFAOYAN
  • Cc1ccc(O)cc1
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 in ethanol miscible
Solubility in diethyl ether miscible
Vapor pressure 0.11 mmHg (25 °C)[1]
−72.1×10−6 cm3/mol
1.5395
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 May be fatal if swallowed, inhaled, or absorbed through skin.
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard
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)

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3
1
0
Flash point 86.1 °C (187.0 °F; 359.2 K)
Explosive limits 1.1%–?[1]
Lethal dose or concentration (LD, LC):
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
Related phenols
 o-cresol, m-cresol, phenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

para-Cresol, also 4-methylphenol, is an organic 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 of phenol and is an isomer of o-cresol and m-cresol.[3]

Production

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Together with many other compounds, p-cresol is conventionally extracted from coal tar, the volatilized materials obtained in the roasting of coal to produce coke. This residue contains a few percent by weight of phenol and cresols. Industrially, p-cresol is currently prepared mainly by a two-step route beginning with the sulfonation of toluene:[4]

CH3C6H5 + H2SO4 → CH3C6H4SO3H + H2O

Basic hydrolysis of the sulfonate salt gives the sodium salt of the cresol:

CH3C6H4SO3H + 2 NaOH → CH3C6H4OH + Na2SO3 + H2O

Other methods for the production of p-cresol include chlorination of toluene followed by hydrolysis. In the cymene-cresol process, toluene is alkylated with propene to give p-cymene, which can be oxidatively dealkylated in a manner similar to the cumene process.[3]

Applications

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p-Cresol is consumed mainly in the production of antioxidants, such as butylated 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]

Natural occurrences

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In humans

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p-Cresol is produced by bacterial fermentation of protein in the human large intestine. It is excreted in feces and urine,[7] and is a component of human sweat that attracts female mosquitoes.[8][9]

p-Cresol is a constituent of tobacco smoke.[10]

In other species

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p-Cresol is a major component in pig odor.[11] Temporal glands secretion examination showed the presence of phenol and p-cresol during musth in male elephants.[12][13] It is one of the very few compounds to attract the orchid bee Euglossa cyanura and has been used to capture and study the species.[14] p-Cresol is a component found in horse urine during estrus that can elicit the Flehmen response.[15]

References

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