Phenol

Phenol
Names
	Preferred IUPAC name Phenol
	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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15882 ;
ChEMBL	ChEMBL14060 ;
ChemSpider	971 ;
DrugBank	DB03255 ;
ECHA InfoCard	100.003.303
KEGG	D00033 ;
PubChem CID	996;
RTECS number	SJ3325000;
UNII	339NCG44TV ;
UN number	2821 (solution); 2312 (molten); 1671 (solid)
CompTox Dashboard (EPA)	DTXSID5021124 ;
	InChI InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H Key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N ; 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
Vapor pressure	0.4 mmHg (20 °C)
Acidity (pKa)	9.95 (in water),; 18.0 (in DMSO),; 29.1 (in acetonitrile);
Conjugate base	Phenoxide
UV-vis (λmax)	270.75 nm
Dipole moment	1.224 D
Pharmacology
ATC code	C05BB05 (WHO) D08AE03 (WHO), N01BX03 (WHO), R02AA19 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H314, H331, H341, H373
Precautionary statements	P261, P280, P301+P310, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 2 0
Flash point	79 °C (174 °F; 352 K)
Explosive limits	1.8–8.6%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	317 mg/kg (rat, oral); 270 mg/kg (mouse, oral);
LDLo (lowest published)	420 mg/kg (rabbit, oral); 500 mg/kg (dog, oral); 80 mg/kg (cat, oral);
LC50 (median concentration)	19 ppm (mammal); 81 ppm (rat); 69 ppm (mouse);
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (19 mg/m3) [skin]
REL (Recommended)	TWA 5 ppm (19 mg/m3); C 15.6 ppm (60 mg/m3) [15-minute] [skin];
IDLH (Immediate danger)	250 ppm
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). verify (what is ?) Infobox references

Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C₆H₅OH.^[5]^[8] It is a white crystalline solid that is volatile and can catch fire.^[5]

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] It is acutely toxic and is considered a health hazard.^[5]^[8]

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, and is a liquid when manufactured.^[5]^[9] It is primarily used to synthesize plastics and related materials.^[8] Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.^[10]

^ "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. ISBN 978-0-85404-182-4. Only one name is retained, phenol, for C₆H₅-OH, both as a preferred name and for general nomenclature.
^ "Phenol_msds".
^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0493". National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ ^a ^b ^c ^d ^e ^f "Phenol". PubChem, US National Library of Medicine. 7 June 2025. Retrieved 9 June 2025.
^ ^a ^b ^c Sigma-Aldrich Co., Phenol. Retrieved on 2022-02-15.
^ ^a ^b ^c "Phenol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c "Medical Management Guidelines for Phenol". National Institute for Occupational Safety and Health, US Centers for Disease Control and Prevention. 21 October 2014. Retrieved 24 June 2025.
^ 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 978-3-527-30673-2.
^ Zvi Rappoport, ed. (2003). The Chemistry of Phenols. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/0470857277. ISBN 9780470857274.

[iupac2013-1] "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. ISBN 978-0-85404-182-4. Only one name is retained, phenol, for C₆H₅-OH, both as a preferred name and for general nomenclature.

[chemsrc-2] "Phenol_msds".

[PGCH-3] 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.

[pubchem-5] ^ ^a ^b ^c ^d ^e ^f "Phenol". PubChem, US National Library of Medicine. 7 June 2025. Retrieved 9 June 2025.

[sigma-6] Sigma-Aldrich Co., Phenol. Retrieved on 2022-02-15.

[IDLH-7] "Phenol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[cdc-8] "Medical Management Guidelines for Phenol". National Institute for Occupational Safety and Health, US Centers for Disease Control and Prevention. 21 October 2014. Retrieved 24 June 2025.

[Ullmann-9] 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 978-3-527-30673-2.

[10] 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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