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] 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]

^ "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 "Phenol". PubChem, US National Library of Medicine. 10 June 2023. Retrieved 12 June 2023.
^ ^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).
^ 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.
^ 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] "Phenol". PubChem, US National Library of Medicine. 10 June 2023. Retrieved 12 June 2023.

[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).

[Ullmann-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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]