2-Chlorophenol

2-Chlorophenol or ortho-chlorophenol is an organic compound with the formula C₆H₄ClOH. It is one of three isomers of monochlorophenol. Aside from occasional use as a disinfectant, it has few applications. It is an intermediate in the polychlorination of phenol.^[8] 2-Chlorophenol is a colorless liquid, although commercial samples are often yellow or amber-colored. It has an unpleasant, penetrating (carbolic) odor. It is poorly soluble in water.

2-Chlorophenol

2-Chlorophenol 2-Chlorophenol
Names
Preferred IUPAC name 2-Chlorophenol[1]
Other names o-Chlorophenol ortho-Chlorophenol 2-Hydroxychlorobenzene
Identifiers
CAS Number	95-57-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:47083 Y
ChEMBL	ChEMBL108877 Y
ChemSpider	13837686 Y
DrugBank	DB03110 Y
ECHA InfoCard	100.002.213
KEGG	C14219 Y
PubChem CID	7245
UNII	K9KAV4K6BN Y
CompTox Dashboard (EPA)	DTXSID5021544
InChI InChI=1S/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H Y Key: ISPYQTSUDJAMAB-UHFFFAOYSA-N Y InChI=1/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H Key: ISPYQTSUDJAMAB-UHFFFAOYAM
SMILES Oc1ccccc1Cl
Properties
Chemical formula	C6H5ClO
Molar mass	128.56 g·mol−1
Appearance	colorless liquid
Density	1.2634 g/cm3 at 20 °C[2]
Melting point	8 °C (46 °F; 281 K)[2]
Boiling point	173.4 °C (344.1 °F; 446.5 K)[2]
Solubility in water	20 g/L at 20 °C
Solubility	Soluble in ethanol, diethyl ether, benzene
Vapor pressure	0.308 kPa[3]
Acidity (pKa)	8.56[4]
Magnetic susceptibility (χ)	-77.3·10−6 cm3/mol[5]
Refractive index (nD)	1.5524[2]
Viscosity	3.59 mPa·s[6]
Thermochemistry[7]
Heat capacity (C)	188.7 J·mol−1·K−1
Enthalpy of fusion (ΔfH⦵fus)	13.0 kJ·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Corrosive – causes burns
Flash point	64 °C (147 °F; 337 K)[6]
Autoignition temperature	550 °C (1,022 °F; 823 K)
Safety data sheet (SDS)	MSDS
Related compounds
Related aromatic hydrocarbons	benzene phenol chlorobenzene
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

See also

• Chlorophenol

References

1. 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 (inactive 2024-06-30). ISBN 978-0-85404-182-4. Only one name is retained, phenol, for C₆H₅-OH, both as a preferred name and for general nomenclature. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p.{{cite book}}: CS1 maint: DOI inactive as of June 2024 (link)
2. Haynes, p. 3.116
3. Haynes, p. 16.20
4. Haynes, p. 5.90
5. Haynes, p. 3.577
6. Haynes, p. 6.243
7. Haynes, pp. 5.10, 6.156
8. Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D.; Paulus, W. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.

Cited sources

• Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

External links

• ToxFAQs for Chlorophenols, Agency for Toxic Substances and Disease Registry.
• Compound Summary Compendium, PubChem Open Chemistry Database.