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Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula C₆H₅OH. 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.

Phenol

Names
Preferred IUPAC name Phenol
Systematic IUPAC name Benzenol
Other names Carbolic acid Phenylic acid Hydroxybenzene Phenic acid
Identifiers
CAS Number	108-95-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15882 Y
ChEMBL	ChEMBL14060 Y
ChemSpider	971 Y
DrugBank	DB03255 Y
ECHA InfoCard	100.003.303
KEGG	D00033 Y
PubChem CID	996
RTECS number	SJ3325000
UNII	339NCG44TV Y
CompTox Dashboard (EPA)	DTXSID5021124
InChI InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H Y Key: ISWSIDIOOBJBQZ-UHFFFAOYSA-N Y 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
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). Y verify (what is YN ?) Infobox references

Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.