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phenol

File:Phenol2.svg · Wikimedia Commons · See Wikimedia Commons

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phenol

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Also known as carbolic acid, PHOH, IPH, IZAL, benzenol, oxybenzene, phenyl hydroxide, phenylic acid

Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.

OverviewAI-generated

Phenol is a chemical compound with the formula C₆H₆O and a molecular mass of 94.042. It has a melting point of 109 and a boiling point of 359. The substance exhibits a density of 1.06 and a vapor pressure of 0.4. Its flash point is 175, with a lower flammable limit of 1.8 and an upper flammable limit of 8.6. The ionization energy is 8.5, and the electric dipole moment is 1.224.

The standard enthalpy of formation for phenol is -162.944. It has a pKa of 9.89 and a solubility of 9. The time-weighted average exposure limit is 19, while the ceiling exposure limit is 60. The concentration immediately dangerous to life or health is 962.5. In terms of molecular properties, phenol has one hydrogen bond donor and one hydrogen bond acceptor, with a topological polar surface area of 20.2 and an xlogp of 1.5.

Synthesized by Vinony from 34 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C6H6O
Molecular weight
94.11 g/mol
IUPAC name
hydron phenoxide
SMILES
[H+].C1=CC=C(C=C1)[O-]
InChIKey
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Polar surface area
23.1 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

via PubChem

Research

732,721 papers

via PubMed

Wikidata facts

Subclass of
phenols
Has part
oxygen
Mass
94.042
Image
Phenol 2 grams.jpg
Has use
medication
Show 28 more facts
density
1.06
immediately dangerous to life or health
962.5
melting point
40.9
Commons category
Phenol
chemical formula
C₆H₆O
NIOSH Pocket Guide ID
0493
boiling point
181.87
vapor pressure
0.4
flash point
175
solubility
9
lower flammable limit
1.8
upper flammable limit
8.6
ionization energy
8.47
time-weighted average exposure limit
19
ceiling exposure limit
60
World Health Organisation international non-proprietary name
phenol
pKa
9.89
found in taxon
Festuca rubra
medical condition treated
pain
canonical SMILES
C1=CC=C(C=C1)O
subject has role
disinfectant
standard enthalpy of formation
-162.944
safety classification and labelling
Regulation (EC) No. 1272/2008
on focus list of Wikimedia project
Wikipedia:Vital articles/Level/4
monomer of
phenol formaldehyde resin
described by source
Encyclopædia Britannica 11th edition
electric dipole moment
1.224
different from
phenols
Sources (8)

via Wikidata · CC0

~21 min read

Encyclopedic overview

27 sections
Contents
  • Properties
  • Acidity
  • Hydrogen bonding
  • Tautomerism
  • Reactions
  • Production
  • Cumene process
  • Oxidation of benzene, toluene, cyclohexylbenzene
  • Older methods
  • Hydrolysis of benzenesulfonic acid
  • Hydrolysis of chlorobenzene
  • Coal pyrolysis
  • Miscellaneous methods
  • Shipping
  • Exposure and toxicity
  • Uses
  • Chemicals
  • Topical anesthetic
  • Nerve block
  • History
  • Second World War
  • Occurrences
  • Biodegradation
  • Naming
  • See also
  • References
  • External links

Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.

The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. It is acutely toxic and is considered a health hazard.

Excerpted from Wikipedia’s “phenol” article, available under the CC BY-SA 4.0 licence.

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