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Phenol information


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
CAS Number
  • 108-95-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15882 checkY
ChEMBL
  • ChEMBL14060 checkY
ChemSpider
  • 971 checkY
DrugBank
  • DB03255 checkY
ECHA InfoCard 100.003.303 Edit this at Wikidata
KEGG
  • D00033 checkY
PubChem CID
  • 996
RTECS number
  • SJ3325000
UNII
  • 339NCG44TV checkY
UN number 2821 (solution)
2312 (molten)
1671 (solid)
CompTox Dashboard (EPA)
  • DTXSID5021124 Edit this at Wikidata
InChI
  • 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
SMILES
  • Oc1ccccc1
Properties
Chemical formula
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)
Solubility in water
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]
Dipole moment
1.224 D
Pharmacology
ATC code
C05BB05 (WHO) D08AE03 (WHO), N01BX03 (WHO), R02AA19 (WHO)
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard[6]
Signal word
Danger
Hazard statements
H301, H311, H314, H331, H341, H373[6]
Precautionary statements
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):
LD50 (median dose)
  • 317 mg/kg (rat, oral)
  • 270 mg/kg (mouse, oral)[7]
LDLo (lowest published)
  • 420 mg/kg (rabbit, oral)
  • 500 mg/kg (dog, oral)
  • 80 mg/kg (cat, oral)[7]
LC50 (median concentration)
  • 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
  • Thiophenol
  • Sodium phenoxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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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Phenol

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Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline...

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In chemistry, a phenol ether (or aromatic ether) is an organic compound derived from phenol (C6H5OH), where the hydroxyl (-OH) group is substituted with...

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Phenol extraction is a laboratory technique that purifies nucleic acid samples using a phenol solution. Phenol is common reagent in extraction because...

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meaning "bitter", due to its bitter taste. It is one of the most acidic phenols. Like other strongly nitrated organic compounds, picric acid is an explosive...

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The Phenol coefficient, is now largely of historical interest, although the principles upon which it is based are still used. It is a measure of the bactericidal...

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Polyphenol

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Polyphenols (/ˌpɒliˈfiːnoʊl, -nɒl/) are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include...

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Phenolic aldehydes are derivatives of phenol. Phenolic aldehydes can be found in wines and cognacs. Examples : Hydroxybenzaldehydes Protocatechuic aldehyde...

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Oxidative coupling of phenols

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Oxidative coupling of phenols is a chemical reaction wherein two phenolic compounds are coupled via an oxidative process. Oxidative phenol couplings are often...

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Cumene process

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The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term...

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Bakelite

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is a thermosetting phenol formaldehyde resin, formed from a condensation reaction of phenol with formaldehyde. The first plastic made...

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Great Phenol Plot

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The Great Phenol Plot was a clandestine effort by the German government during the early years of World War I to divert American-produced phenol from the...

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Cresol

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widely-occurring phenols (sometimes called phenolics) which may be either natural or manufactured. They are also categorized as methyl phenols. Cresols commonly...

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Phenolic content in wine

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The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical...

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Phenolic lipids are a class of natural products composed of long aliphatic chains and phenolic rings. Phenolic lipids occur in plants, fungi and bacteria...

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Phenolic paper

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Phenolic paper is a material often used to make printed circuit board substrates (the flat board to which the components and traces are attached). It is...

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Bisphenol A

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BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region...

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