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;
Abbreviations	PhOH
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 C1=CC=C(C=C1)O;
Properties
Chemical formula	C6H6O
Molar mass	94.113 g·mol−1
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)
Related compounds
Related compounds	Thiophenol; Benzeneselenol; Benzenetellurol; Sodium phenoxide; Catechol; Resorcinol; Hydroquinone; Phloroglucinol; Pyrogallol; Hydroxyquinol; 1,2,3,5-Tetrahydroxybenzene; Pentahydroxybenzene; Benzenehexol;
	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. It is a white crystalline solid that is volatile and can catch fire.

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. It is acutely toxic and is considered a health hazard.

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. It is primarily used to synthesize plastics and related materials. 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.