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Phenol

This article is about the molecule. For the group of chemicals that contains a phenol group, see Phenols.
"Carbolic acid" redirects here. Not to be confused with carbonic acid or carboxylic acid.
Phenol
Names
Preferred IUPAC name
Phenol[1]
Systematic IUPAC name
Benzenol
Other names
  • Carbolic acid
  • Phenolic acid
  • Phenylic acid
  • Hydroxybenzene
  • Phenic acid
  • Phenyl alcohol
  • Phenyl hydroxide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.303 Edit this at Wikidata
KEGG
RTECS number
  • SJ3325000
UNII
UN number 2821 (solution)
2312 (molten)
1671 (solid)
  • InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H checkY
    Key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
  • Oc1ccccc1
Properties
C6H6O
Molar mass 94.113 g/mol
Appearance Transparent crystalline solid
Odor Sweet and tarry
Density 1.07 g/cm3
Melting point 40.5 °C (104.9 °F; 313.6 K)
Boiling point 181.7 °C (359.1 °F; 454.8 K)
8.3 g/100 mL (20 °C)
log P 1.48[2]
Vapor pressure 0.4 mmHg (20 °C)[3]
Acidity (pKa)
  • 9.95 (in water),
  • 18.0 (in DMSO),
  • 29.1 (in acetonitrile)[4]
Conjugate base Phenoxide
UV-vis (λmax) 270.75 nm[5]
1.224 D
Pharmacology
C05BB05 (WHO) D08AE03 (WHO), N01BX03 (WHO), R02AA19 (WHO)
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard[6]
Danger
H301, H311, H314, H331, H341, H373[6]
P261, P280, P301+P310, P305+P351+P338, P310[6]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 79 °C (174 °F; 352 K)
Explosive limits 1.8–8.6%[3]
Lethal dose or concentration (LD, LC):
  • 317 mg/kg (rat, oral)
  • 270 mg/kg (mouse, oral)[7]
  • 420 mg/kg (rabbit, oral)
  • 500 mg/kg (dog, oral)
  • 80 mg/kg (cat, oral)[7]
  • 19 ppm (mammal)
  • 81 ppm (rat)
  • 69 ppm (mouse)[7]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 ppm (19 mg/m3) [skin][3]
REL (Recommended)
  • TWA 5 ppm (19 mg/m3)
  • C 15.6 ppm (60 mg/m3) [15-minute] [skin][3]
IDLH (Immediate danger)
 250 ppm[3]
Safety data sheet (SDS) [1]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C6H5OH.[5] It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns.[5]

Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds.[8] It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.[9]

  1. ^ "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001 (inactive 2024-04-14). ISBN 978-0-85404-182-4. Only one name is retained, phenol, for C6H5-OH, both as a preferred name and for general nomenclature.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
  2. ^ "Phenol_msds".
  3. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0493". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Kütt, Agnes; Movchun, Valeria; Rodima, Toomas; et al. (2008). "Pentakis(trifluoromethyl)phenyl, a Sterically Crowded and Electron-withdrawing Group: Synthesis and Acidity of Pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline". The Journal of Organic Chemistry. 73 (7): 2607–20. doi:10.1021/jo702513w. PMID 18324831.
  5. ^ a b c "Phenol". PubChem, US National Library of Medicine. 10 June 2023. Retrieved 12 June 2023.
  6. ^ a b c Sigma-Aldrich Co., Phenol. Retrieved on 2022-02-15.
  7. ^ a b c "Phenol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  8. ^ Weber, Manfred; Weber, Markus; Kleine-Boymann, Michael (2004). "Phenol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_299.pub3. ISBN 978-3527306732.
  9. ^ Zvi Rappoport, ed. (2003). The Chemistry of Phenols. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/0470857277. ISBN 9780470857274.

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