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Revision as of 18:21, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 453487333 of page 4-Nitrophenol for the Chem/Drugbox validation project (updated: '').		Latest revision as of 10:07, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits added Category:4-Hydroxyphenyl compounds using HotCat
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			{{Chembox
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			| Watchedfields = changed
	{{chembox
	| verifiedrevid = 443655101		| verifiedrevid = 477223170
⚫	| ImageFileR1 = 4-nitrophenol-sample.jpg
	| ImageSizeR1 = 150px
	| ImageFileL1 = 4-Nitrophenol acsv.svg		| ImageFileL1 = 4-Nitrophenol acsv.svg
	| ImageSizeL1 = 150px		| ImageSizeL1 = 140
	| IUPACName = 4-Nitrophenol		| ImageFileR1 = 4-Nitrophenol-3D-balls-2.png
		⚫	| ImageFile2 = 4-nitrophenol-sample.jpg
	| OtherNames = ''p''-Nitrophenol<br />''para''-Nitrophenol<br>4-Hydroxynitrobenzene<br />PNP
			| ImageSize2 = 180
⚫	| Section1 = {{Chembox Identifiers
			| ImageAlt2 = Coarse yellow crystals
⚫	| KEGG_Ref = {{keggcite|correct|kegg}}
			| PIN = 4-Nitrophenol
			| OtherNames = ''p''-Nitrophenol<ref name=iupac2013>This is no longer a recommended IUPAC name: {{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><br />''para''-Nitrophenol<br />4-Hydroxynitrobenzene<br />PNP
		⚫	|Section1={{Chembox Identifiers
		⚫	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C00870		| KEGG = C00870
	| InChI = 1/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H		| InChI = 1/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 100-02-7		| CASNo = 100-02-7
	| PubChem = 980		| PubChem = 980
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 955		| ChemSpiderID = 955
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = Y92ZL45L4R		| UNII = Y92ZL45L4R
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
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	| SMILES = O=()c1ccc(O)cc1		| SMILES = O=()c1ccc(O)cc1
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 6 | H = 5 | N = 1 | O = 3		| C=6 | H=5 | N=1 | O=3
	| Appearance = Colorless or yellow pillars		| Appearance =Colourless to pale yellow crystals
	| Density =		| Density =
			| MeltingPtC = 113 to 114
	| MeltingPt = 113–114 °C
	| BoilingPtC = 279		| MeltingPt_notes =
			| BoilingPtC = 279
⚫	| Solubility = 10 g/L (15 °C)<br />11.6 g/L (20 °C)<br />16 g/L (25 °C)
			| pKa = 7.15 (in water),
⚫	}}
		⚫	| Solubility = 10 g/L (15 °C)<br />11.6 g/L (20 °C)<br />16 g/L (25 °C)
⚫	| Section3 = {{Chembox Hazards
			| MagSus = -69.5·10<sup>−6</sup> cm<sup>3</sup>/mol
⚫	| MainHazards =
⚫	| FlashPt =
	| Autoignition =
	}}		}}
		⚫	|Section3={{Chembox Hazards
		⚫	| MainHazards =
		⚫	| FlashPt =
			| AutoignitionPt =
		⚫	}}
			}}
			'''4-Nitrophenol''' (also called '''''p''-nitrophenol''' or '''4-hydroxynitrobenzene''') is a ] compound that has a ] at the opposite position of the hydroxyl group on the benzene ring.
			==Properties==
			4-nitro phenol is a slightly yellow, crystalline material, moderately toxic.
			It shows two ]s in the crystalline state. The alpha-form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta-form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms.
			In solution, 4-nitrophenol has a ] (pK<sub>a</sub>) of 7.15 at 25&nbsp;°C.<ref>{{Cite web|url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+100-02-7|title=TOXNET|website=toxnet.nlm.nih.gov|access-date=2016-10-28}}</ref>
			== Preparation ==
			=== From phenol ===
			4-Nitrophenol can be prepared by ] of ] using dilute ] at room temperature. The reaction produces a mixture of ] and 4-nitrophenol.
			:]{{clear-left}}
			==Uses==
			===pH indicator===
			{{pH indicator template
			| indicator_name = 4-Nitrophenol
			| low_pH = 5.4
			| low_pH_color =
			| low_pH_text =
			| high_pH = 7.5
			| high_pH_color = Yellow
			| high_ph_text =
	}}		}}
			4-Nitrophenol can be used as a ]. A solution of 4-nitrophenol appears colorless below pH 5.4 and yellow above pH 7.5.<ref>{{Cite web|url=http://www.merckmillipore.com/INTL/en/product/4-Nitrophenol,MDA_CHEM-106798|title=4-Nitrophenol CAS 100-02-7 {{!}} 106798|website=www.merckmillipore.com|access-date=2016-10-28}}</ref> This color-changing property makes this compound useful as a ].
			The yellow color of the 4-nitrophenolate form (or 4-nitro]) is due to a maximum of absorbance at 405&nbsp;nm (ε = 18.3 to 18.4 mM<sup>−1</sup> cm<sup>−1</sup> in strong alkali).<ref name=absorbance>{{cite journal|last1=Bowers|first1=G.N.|last2=McComb|first2=R.B.|last3=Christensen|first3=R.C.|last4=Schaffer|first4=R.|title=High-Purity 4-Nitrophenol: Purification, Characterization, and Specifications for Use as a Spectrophotometric Reference Material|journal=Clinical Chemistry|date=1980|volume=26|issue=6|pages=724–729|pmid=7371150|url=http://www.clinchem.org/clinchem/article/26/6/724/5664415|doi=10.1093/clinchem/26.6.724|doi-access=free}}</ref> In contrast, 4-nitrophenol has a weak absorbance at 405&nbsp;nm (ε = 0.2 mM<sup>−1</sup> cm<sup>−1</sup>).<ref name=absorbance />
			The ] for 4-nitrophenol/4-nitrophenoxide is at 348&nbsp;nm, with ε = 5.4 mM<sup>−1</sup> cm<sup>−1</sup>.<ref name=isosbestic>{{cite journal|last1=Biggs|first1=A.I.|title=A spectrophotometric determination of the dissociation constants of p-nitrophenol and papaverine|journal=Transactions of the Faraday Society|date=1954|volume=50|issue=50|pages=800–802|doi=10.1039/tf9545000800}}</ref>
			===Other uses===
			*4-Nitrophenol is an intermediate in the synthesis of ]. It is reduced to ], then acetylated with ].<ref>{{cite book |author=Ellis, Frank |title=Paracetamol: a curriculum resource |publisher=Royal Society of Chemistry |location=Cambridge |year=2002 |isbn=0-85404-375-6 }}</ref>
			* 4-Nitrophenol is used as the precursor for the preparation of ] and ], indicators, and raw materials for fungicides. ] of this compound rarely occurs.
			* In ], ] derivatives of 4-nitrophenol may serve as activated components for construction of ] moieties.
			===Uses of derivatives===
			In the laboratory, it is used to detect the presence of ] activity by hydrolysis of ]. In basic conditions, presence of hydrolytic enzymes will turn reaction vessel yellow.<ref>{{Cite book|title=Fundamental Laboratory Approached for Biochemistry and Biotechnology|last=Ninfa|first=Alexander|publisher=Wiley|year=2010|isbn=978-0470087664|pages=153, 243}}</ref>
			4-Nitrophenol is a product of the enzymatic cleavage of several synthetic substrates such as 4-nitrophenyl phosphate (used as a substrate for ]), 4-nitrophenyl acetate (for ]), 4-nitrophenyl-β-<small>D</small>-glucopyranoside and other sugar derivatives which are used to assay various ] enzymes. Amounts of 4-nitrophenol produced by a particular ] in the presence of its corresponding substrate can be measured with a ] at or around 405&nbsp;nm and used as a proxy measurement for the amount of the enzyme activity in the sample.
			Accurate measurement of enzyme activity requires that the 4-nitrophenol product is fully deprotonated, existing as 4-nitrophenolate, given the weak absorbance of 4-nitrophenol at 405&nbsp;nm. Complete ionization of the alcohol functional group affects the conjugation of the pi bonds on the compound. A lone pair from the oxygen can be delocalized via conjugation to the benzene ring and nitro group. Since the length of conjugated systems affects the color of organic compounds, this ionization change causes the 4-nitrophenol to turn yellow when fully deprotonated and existing as 4-nitrophenolate.<ref>{{Cite web|url=http://www.shimadzu.com/an/uv/support/uv/ap/apl.html|title=The Relationship Between UV-VIS Absorption and Structure of Organic Compounds|website=Shimadzu|access-date=May 14, 2017}}</ref>
			A common mistake in measuring enzyme activity using these substrates is to perform the assays at neutral or acidic pH without considering that only part of the chromophoric product is ionized. The problem can be overcome by stopping the reaction with ] (NaOH) or other strong base, which converts all product into 4-nitrophenoxide; final pH must be > ''ca.'' 9.2 to ensure more than 99% of the product is ionised. Alternatively enzyme activity can be measured at 348&nbsp;nm, the ] for 4-nitrophenol/4-nitrophenoxide.
			==Toxicity==
			4-Nitrophenol irritates the eyes, skin, and respiratory tract.<ref name=toxprofile>{{Cite report | url = http://www.atsdr.cdc.gov/toxprofiles/tp50.pdf | title = Toxicological Profile For Nitrophenols | publisher = Agency for Toxic Substances and Disease Registry, U.S. Public Health Service | date = July 1992}}</ref> It may also cause inflammation of those parts. It has a delayed interaction with blood and forms ] which is responsible for ], potentially causing cyanosis, confusion, and unconsciousness.<ref name=toxprofile/> When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response. Genotoxicity and carcinogenicity of 4-nitrophenol are not known. The {{LD50}} in mice is 282&nbsp;mg/kg and in rats is 202&nbsp;mg/kg (p.o.).
			==See also==
			*]
			==References==
			{{Reflist}}
			{{DEFAULTSORT:Nitrophenol, 4-}}
			]
			]
			]