2-Chlorophenol: Difference between revisions

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	{{chembox		{{chembox
			\| Watchedfields = changed
	\| verifiedrevid = 444961058
			\| verifiedrevid = 477213052
	\| Name = 2-Chlorophenol
			\| Name = 2-Chlorophenol
	\| Reference = <ref name="hand">
			\| Reference =
	{{Citation
			\| ImageFileL1 = 2-Chlorphenol.svg
	\| last = Lide
			\| ImageNameL1 = 2-Chlorophenol
	\| first = David R.
			\| ImageFileR1 = 2-chlorophenol.png
	\| author-link =
			\| ImageNameR1 = 2-Chlorophenol
	\| last2 =
			\| PIN = 2-Chlorophenol<ref name=iupac2013>{{cite book \| title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) \| publisher = ] \| date = 2014 \| location = Cambridge \| page = 690 \| doi = 10.1039/9781849733069-FP001 \| isbn = 978-0-85404-182-4 \| quote = Only one name is retained, phenol, for C<sub>6</sub>H<sub>5</sub>-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''.}}</ref>
	\| first2 =
			\| OtherNames = ''o''-Chlorophenol<br />''ortho''-Chlorophenol<br>2-Hydroxychlorobenzene
	\| author2-link =
			\|Section1={{Chembox Identifiers
	\| publication-date =
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| date =
	\| year = 1998
	\| title = Handbook of Chemistry and Physics
	\| edition = 87
	\| volume =
	\| series =
	\| publication-place = Boca Raton, FL
	\| place =
	\| publisher = CRC Press
	\| id =
	\| isbn = 0-8493-0594-2
	\| doi =
	\| oclc =
	\| pages = 3–120
	\| url =
	\| accessdate =
	\| postscript = <!--none-->
	}}</ref><ref name="hand2">
	{{Citation
	\| last = Lide
	\| first = David R.
	\| author-link =
	\| last2 =
	\| first2 =
	\| author2-link =
	\| publication-date =
	\| date =
	\| year = 1998
	\| title = Handbook of Chemistry and Physics
	\| edition = 87
	\| volume =
	\| series =
	\| publication-place = Boca Raton, FL
	\| place =
	\| publisher = CRC Press
	\| id =
	\| isbn = 0-8493-0594-2
	\| doi =
	\| oclc =
	\| pages = 1281
	\| url =
	\| accessdate =
	\| postscript = <!--none-->
	}}</ref><ref name="hand3">
	{{Citation
	\| last = Lide
	\| first = David R.
	\| author-link =
	\| last2 =
	\| first2 =
	\| author2-link =
	\| publication-date =
	\| date =
	\| year = 1998
	\| title = Handbook of Chemistry and Physics
	\| edition = 87
	\| volume =
	\| series =
	\| publication-place = Boca Raton, FL
	\| place =
	\| publisher = CRC Press
	\| id =
	\| isbn = 0-8493-0594-2
	\| doi =
	\| oclc =
	\| pages = 8–103
	\| url =
	\| accessdate =
	\| postscript = <!--none-->
	}}</ref><ref name="hand4">
	{{Citation
	\| last = Lide
	\| first = David R.
	\| author-link =
	\| last2 =
	\| first2 =
	\| author2-link =
	\| publication-date =
	\| date =
	\| year = 1998
	\| title = Handbook of Chemistry and Physics
	\| edition = 87
	\| volume =
	\| series =
	\| publication-place = Boca Raton, FL
	\| place =
	\| publisher = CRC Press
	\| id =
	\| isbn = 0-8493-0594-2
	\| doi =
	\| oclc =
	\| pages = 15–18
	\| url =
	\| accessdate =
	\| postscript = <!--none-->
	}}</ref>
	\| ImageFileL1 = 2-Chlorphenol.svg
	\| ImageSizeL1 = 120px
	\| ImageNameL1 = 2-Chlorophenol
	\| ImageFileR1 = 2-chlorophenol.png
	\| ImageSizeR1 = 120px
	\| ImageNameR1 = 2-Chlorophenol
	\| IUPACName = 2-Chlorophenol
	\| OtherNames = 2-Hydroxychlorobenzene, ''o''-Chlorophenol
	\| Section1 = {{Chembox Identifiers
	\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 47083		\| ChEBI = 47083
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = DB03110		\| DrugBank = DB03110
	\| SMILES = Oc1ccccc1Cl		\| SMILES = Oc1ccccc1Cl
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = C14219		\| KEGG = C14219
	\| InChI = 1/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H		\| InChI = 1/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H
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	\| StdInChIKey = ISPYQTSUDJAMAB-UHFFFAOYSA-N		\| StdInChIKey = ISPYQTSUDJAMAB-UHFFFAOYSA-N
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 95-57-8		\| CASNo = 95-57-8
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| CASNo_valid = yes
			\| UNII = K9KAV4K6BN
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 13837686		\| ChemSpiderID = 13837686
			\| PubChem = 7245
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=6 \| H=5 \| Cl=1 \| O=1
	\| Formula = C<sub>6</sub>H<sub>5</sub>ClO
			\| Appearance = colorless liquid
	\| MolarMass = 128.56 g/mol
			\| Density = 1.2634 g/cm<sup>3</sup> at 20 °C<ref name=crc/>
	\| Appearance = Light amber, liquid
	\| ~~Density~~ = ~~1.2634~~ g/~~cm<sup>3</sup>~~ at 20 °C		\| Solubility = 20 g/L at 20 °C
			\| SolubleOther = Soluble in ], ], ]
	\| Solubility = 20 g/L at 20 °C
			\| MeltingPtC = 8
	\| SolubleOther = soluble in ], ], ]
			\| MeltingPt_ref =<ref name=crc>Haynes, p. 3.116</ref>
	\| MeltingPt = 9.4 °C
	\| ~~BoilingPt~~ = ~~174~~.~~9 °C~~		\| BoilingPtC = 173.4
			\| BoilingPt_ref =<ref name=crc/>
	\| pKa = 8.56
			\| RefractIndex = 1.5524<ref name=crc/>
	\| VaporPressure = 0.308 kPa
			\| pKa = 8.56<ref>Haynes, p. 5.90</ref>
			\| VaporPressure = 0.308 kPa<ref>Haynes, p. 16.20</ref>
			\| Viscosity = 3.59 mPa·s<ref name=crc2>Haynes, p. 6.243</ref>
			\| MagSus = -77.3·10<sup>−6</sup> cm<sup>3</sup>/mol<ref>Haynes, p. 3.577</ref>
	}}		}}
	\| Section4 = {{Chembox Thermochemistry		\|Section4={{Chembox Thermochemistry
			\| Thermochemistry_ref=<ref>Haynes, pp. 5.10, 6.156</ref>
	\| DeltaHf =
	\| ~~DeltaHc~~ =		\| DeltaHf =
	\| ~~Entropy~~ =		\| DeltaHc =
			\| Entropy =
	\| HeatCapacity = 1.468 J·g<sup>-1</sup>·K<sup>-1</sup>
			\| HeatCapacity = 188.7 J·mol<sup>−1</sup>·K<sup>−1</sup>
			\| DeltaHfus = 13.0 kJ·mol<sup>−1</sup>
	}}		}}
	\| Section7 = {{Chembox Hazards		\|Section7={{Chembox Hazards
			\| ExternalSDS =
	\| Autoignition = 550 °C
			\| MainHazards = Corrosive – causes burns
	\| ExternalMSDS =
			\| FlashPtC = 64
	\| MainHazards = Corrosive - causes burns
			\| FlashPt_ref = <ref name=crc2/>
	\| FlashPt = 64°C
			\| AutoignitionPtC = 550
	}}		}}
	\| Section8 = {{Chembox Related		\|Section8={{Chembox Related
	\| ~~Function~~ = ]		\| OtherFunction_label = ]
	\| ~~OtherFunctn~~ = ]<br />]<br />]		\| OtherFunction = ]<br />]<br />]
	}}		}}
	}}		}}

	'''2-Chlorophenol''' or '''''ortho''-chlorophenol''' is an ], a ~~derivative~~ of ]. ~~Related~~ ~~compounds~~ ~~are~~ ~~used~~ ~~as a~~ ] ~~agents and various~~ ]. ~~This~~ ~~particular~~ ~~compound~~ has few applications, ~~but~~ is an intermediate in the poly] of phenol.<ref>{{~~Citation~~		'''2-Chlorophenol''' or '''''ortho''-chlorophenol''' is an ] with the formula C<sub>6</sub>H<sub>4</sub>ClOH. It is one of three ]s of ]. Aside from occasional use as a ], it has few applications. It is an intermediate in the poly] of phenol.<ref>{{Ullmann
	\| ~~author~~ = Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D.; Paulus, W.		\|author1=Fiege, H. \|author2=Voges, H.-M. \|author3=Hamamoto, T \|author4=Umemura, S. \|author5=Iwata, T. \|author6=Miki, H. \|author7=Fujita, Y. \|author8=Buysch, H.-J. \|author9=Garbe, D. \|author10=Paulus, W. \| title = Phenol Derivatives
			\| year = 2000
	\| title = Phenol Derivatives
			\| doi = 10.1002/14356007.a19_313}}</ref>
	\| journal = Ullmann's Encyclopedia of Industrial Chemistry
			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.
	\| volume =
	\| issue =
	\| pages =
	\| year = 2000
	\| publisher = Wiley-VCH
	\| location = Weinheim
	\| doi = 10.1002/14356007.a19_313
	\| postscript = <!--none--> }}</ref>

	==See also==		==See also==
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	==References==		==References==
	{{Reflist}}		{{Reflist}}

			==Cited sources==
			*{{cite book \|ref=Haynes\| editor= Haynes, William M. \| date = 2016\| title = ] \| edition = 97th \| publisher = ] \| isbn = 9781498754293}}

	==External links==		==External links==
	* , Agency for Toxic Substances and Disease Registry.		* , Agency for Toxic Substances and Disease Registry.
			* , PubChem Open Chemistry Database.

	{{DEFAULTSORT:Chlorophenol, 2-}}		{{DEFAULTSORT:Chlorophenol, 2-}}
	]		]
	]		]
	]		]
	]		]

	{{Organohalide-stub}}		{{Organohalide-stub}}

	]
	]
	]
	]

Latest revision as of 09:03, 23 October 2024

2-Chlorophenol

Names

Preferred IUPAC name 2-Chlorophenol

Other names o-Chlorophenol
ortho-Chlorophenol
2-Hydroxychlorobenzene

Identifiers

CAS Number

95-57-8

3D model (JSmol)

Interactive image

ChEBI

CHEBI:47083

ChEMBL

ChEMBL108877

ChemSpider

13837686

DrugBank

DB03110

ECHA InfoCard

100.002.213

KEGG

C14219

PubChem CID

7245

UNII

K9KAV4K6BN

CompTox Dashboard (EPA)

DTXSID5021544

InChI

InChI=1S/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8HKey: ISPYQTSUDJAMAB-UHFFFAOYSA-N
InChI=1/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8HKey: ISPYQTSUDJAMAB-UHFFFAOYAM

SMILES

Oc1ccccc1Cl

Properties

Chemical formula

C₆H₅ClO

Molar mass

128.56 g·mol

Appearance

colorless liquid

Density

1.2634 g/cm at 20 °C

Melting point

8 °C (46 °F; 281 K)

Boiling point

173.4 °C (344.1 °F; 446.5 K)

Solubility in water

20 g/L at 20 °C

Solubility

Soluble in ethanol, diethyl ether, benzene

Vapor pressure

0.308 kPa

Acidity (pK_a)

8.56

Magnetic susceptibility (χ)

-77.3·10 cm/mol

Refractive index (n_D)

1.5524

Viscosity

3.59 mPa·s

Thermochemistry

Heat capacity (C)

188.7 J·mol·K

Enthalpy of fusion (Δ_fH_fus)

13.0 kJ·mol

Hazards

Occupational safety and health (OHS/OSH):

Main hazards

Corrosive – causes burns

Flash point

64 °C (147 °F; 337 K)

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 , 100 kPa).

Y verify (what is ?) Infobox references

Chemical compound

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. 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.

References

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. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p.
^ Haynes, p. 3.116
Haynes, p. 16.20
Haynes, p. 5.90
Haynes, p. 3.577
^ Haynes, p. 6.243
Haynes, pp. 5.10, 6.156
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 978-3-527-30673-2.

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.

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Latest revision as of 09:03, 23 October 2024

See also

References

Cited sources

External links