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Revision as of 23:23, 6 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'ChEBI').← Previous edit		Latest revision as of 12:55, 17 September 2024 edit undoPreimage (talk | contribs)Extended confirmed users729 edits →Chembox OtherNames: Remove dibenzene - well-meaning but incorrect, added in 08:56, 30 January 2023
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			{{For|the compound including hydroxyl groups|Bisphenol}}
	{{chembox| verifiedrevid = 414030198
			{{Redirect|Lemonene|the monoterpene in citrus oil|Limonene}}
	|
			{{Chembox
			| Verifiedfields = changed
			| Watchedfields = changed
			| verifiedrevid = 443423597
	| ImageFile = Bifenyl.svg		| ImageFile = Bifenyl.svg
	| ImageName = Skeletal formula		| ImageName = Skeletal formula
	| ImageFile1 = Biphenyl 3D.png		| ImageFile1 = Biphenyl-3D-vdW.png
	| ImageSize1 = 200px		| ImageSize1 = 200px
	| ImageName1 = Space filling model showing its twisted conformation		| ImageName1 = Space filling model showing its twisted conformation
			| ImageFile2 = BiphenylSample.jpg
	| IUPACName = Biphenyl
			| ImageSize2 = 200px
	| Section1 = {{Chembox Identifiers
			| ImageName2 = sample
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| PIN = 1,1′-Biphenyl <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
			| OtherNames = {{Unbulleted list|Biphenyl|Phenylbenzene|Xenene}}
			|Section1={{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6828		| ChemSpiderID = 6828
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C06588		| KEGG = C06588
			| Gmelin = 3808
			| Beilstein = 1634058
			| EINECS = 202-163-5
			| RTECS = DU8050000
			| UNNumber = 3077
			| 3DMet = B00985
	| InChI = 1/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H		| InChI = 1/C12H10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10H
	| InChIKey = ZUOUZKKEUPVFJK-UHFFFAOYAV		| InChIKey = ZUOUZKKEUPVFJK-UHFFFAOYAV
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	| StdInChIKey = ZUOUZKKEUPVFJK-UHFFFAOYSA-N		| StdInChIKey = ZUOUZKKEUPVFJK-UHFFFAOYSA-N
	| CASNo = 92-52-4		| CASNo = 92-52-4
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 2L9GJK6MGN
			| UNII = 2L9GJK6MGN
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 17097		| ChEBI = 17097
	| SMILES = c1ccc(cc1)c2ccccc2		| SMILES = c1ccccc1-c2ccccc2
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| PubChem = 7095
	}}
			}}
	| Section2={{Chembox Properties
			|Section2={{Chembox Properties
	| C=12
	| H=10		| C=12 | H=10
	| Density=1.04 g/cm<sup>3</sup>		| Density=1.04 g/cm<sup>3</sup><ref name=GESTIS>{{GESTIS|ZVG=13450}}</ref>
	| Appearance = colorless crystals		| Appearance = Colorless to pale-yellow crystals
			| Odor = pleasant<ref name=PGCH/>
	| MeltingPtC=68.93
			| MeltingPtC=69.2
	| BoilingPtC=256
			| MeltingPt_ref = <ref name=GESTIS/>
	| Solubility=Insoluble
			| BoilingPtC=255
	| Solvent=Water
			| BoilingPt_ref = <ref name=GESTIS/>
			| Solubility=4.45 mg/L<ref name=GESTIS/>
			| VaporPressure = 0.005 mmHg (20°C)<ref name=PGCH/>
			| MagSus = −103.25·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section14={{Chembox Hazards		|Section4={{Chembox Hazards
			| NFPA-H=1
	| EUClass=Irritant ('''Xi''')<br/>Dangerous for<br/>the environment ('''N''')
			| NFPA-F=1
	| EUIndex=601-042-00-8
	| NFPA-H=1		| NFPA-R=0
			| GHSPictograms = {{GHS07}}{{GHS09}}
	| NFPA-F=1
			| GHSSignalWord = Warning
	| NFPA-R=0
			| HPhrases = {{H-phrases|315|319|335|410}}
	| RPhrases={{R36/37/38}}, {{R50/53}}
			| PPhrases = {{P-phrases|261|264|271|273|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|391|403+233|405|501}}
	| SPhrases={{S2}}, {{S23}}, {{S60}}, {{S61}}
	| FlashPt=113 °C		| FlashPtC=113
			| FlashPt_ref=<ref name=GESTIS/>
	| Autoignition=540 °C
			| AutoignitionPtC=540
			| AutoignitionPt_ref =<ref name=GESTIS/>
			| PEL = TWA 1 mg/m<sup>3</sup> (0.2 ppm)<ref name=PGCH>{{PGCH|0239}}</ref>
			| ExploLimits = 0.6–5.8%<ref name=PGCH/>
			| IDLH = 100 mg/m<sup>3</sup><ref name=PGCH/>
			| LD50 = 2400 mg/kg (oral, rabbit)<br/>3280 mg/kg (oral, rat)<br/>1900 mg/kg (oral, mouse)<br/>2400 mg/kg (oral, rat)<ref>{{cite web |url = https://www.cdc.gov/niosh/idlh/92524.html |title = Diphenyl |work = Immediately Dangerous to Life or Health Concentrations (IDLH) |publisher = National Institute for Occupational Safety and Health (NIOSH) |date = 4 December 2014 |access-date = 17 March 2015}}</ref>
			| REL = TWA 1 mg/m<sup>3</sup> (0.2 ppm)<ref name=PGCH/>
	}}		}}
	}}		}}
			'''Biphenyl''' (also known as '''diphenyl''', '''phenylbenzene''', '''1,1′-biphenyl''', '''lemonene'''<ref>{{cite web |title=Biphenyl |url=https://webbook.nist.gov/cgi/cbook.cgi?ID=92-52-4 |website=NIST Chemistry WebBook |publisher=US ]}} An obscure name, according to {{cite web |title=Limonene |url=https://www.acs.org/molecule-of-the-week/archive/l/limonene.html |website=Molecule of the Week Archive |publisher=] |date=Nov 1, 2021}}</ref> or '''BP''') is an ] that forms colorless crystals. Particularly in older literature, compounds containing the ] consisting of biphenyl less one hydrogen (the site at which it is attached) may use the prefixes '''xenyl''' or '''diphenylyl'''.<ref>{{cite web|url=https://archive.org/stream/beilsteinshandb01gesegoog/beilsteinshandb01gesegoog_djvu.txt|title=Beilsteins Handbuch der organischen Chemie, Volume 5}}</ref>
	{{distinguish|limonene|bisphenol}}
	'''Biphenyl''' (or '''diphenyl''' or '''phenylbenzene''' or '''1,1'-biphenyl''' or '''lemonene''') is an ] that forms colorless crystals. It has a distinctively pleasant smell. Biphenyl is an ] with a ] (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>. It is notable as a starting material for the production of ]s (PCBs), which were once widely used as ] fluids and ] agents. Biphenyl is also an intermediate for the production of a host of other ]s such as ]s, ]s, ] products, and ]s.
			It has a distinctively pleasant smell. Biphenyl is an ] with a ] (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>. It is notable as a starting material for the production of ]s (PCBs), which were once widely used as ] fluids and ] agents.
	== Properties ==
	Biphenyl occurs naturally in ], ], and ] and can be isolated from these sources via ]. It can also be synthesized by using a ] such as ] and reacting it with ]. Biphenyl is ] in water, but soluble in typical ]s. The biphenyl molecule consists of two connected ]s. Lacking functional groups, it is fairly non-reactive. It will, however, participate in many of the reactions that are typical for benzene, for example, ] reactions upon treatment with halogens in the presence of a ].
			Biphenyl is also an intermediate for the production of a host of other ]s such as ]s, ]s, ] products, and ]s. Biphenyl is ] in water, but soluble in typical ]s. The biphenyl molecule consists of two connected ]s.
	==Stereochemistry==
	Rotation about the single bond in biphenyl, and especially its ] derivatives, is ]. For this reason, some substituted biphenyls show ]; that is, the individual C<sub>2</sub>-]-isomers are ]. Some derivatives, as well as related molecules such as ], find application as ]s in ]. In the case of unsubstituted biphenyl, the equilibrium torsional angle is 44.4° and the torsional barriers are quite small, 6.0 kJ/mol at 0° and 6.5 kJ/mol at 90°.<ref>{{cite journal |journal=J. Chem. Theory Comput. |doi=10.1021/ct800182e |title=Torsional Barriers and Equilibrium Angle of Biphenyl: Reconciling Theory with Experiment |year=2008 |author=Mikael P. Johansson and Jeppe Olsen |volume=4 |pages=1460}}</ref> Adding ortho substituents greatly increases the barrier: in the case of the 2,2'-dimethyl derivative, the barrier is 17.4 kcal/mol (72.8 kJ/mol).<ref>{{cite book |title=Stereochemistry |editor=Christoph Tamm |author=B. Testa |pages=18 |publisher=Elsevier |year=1982 |chapter=The geometry of molecules: basic principles and nomenclatures}}</ref>
			==Properties and occurrence==
	==Biological aspects==
			Biphenyl is a solid at room temperature, with a melting point of {{convert|69.2|C}}. In the gas phase the molecule exists in two ] twisted forms with an angle between the planes of the two rings of 44.4°. In the room-temperature solid, biphenyl is crystalline with ] P2{{sub|1}}/c, which does not allow for ] crystals. Rather than there being a ] entailing the two twisted conformations, the potential energy is minimized at zero twist.<ref>{{cite journal |last1=Dr. Bruno Landeros-Rivera, Jesús Hernández-Trujillo |title=Control of Molecular Conformation and Crystal Packing of Biphenyl Derivatives |journal=] |date=Dec 15, 2021 |volume=87 |doi=10.1002/cplu.202100492 |url=https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cplu.202100492}}</ref><ref>{{Cite journal |last1=Landeros-Rivera |first1=Bruno |last2=Jancik |first2=Vojtech |last3=Moreno-Esparza |first3=Rafael |last4=Martínez Otero |first4=Diego |last5=Hernández-Trujillo |first5=Jesús |date=May 27, 2021 |title=Non-Covalent Interactions in the Biphenyl Crystal: Is the Planar Conformer a Transition State? |url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202101490 |journal=] |language=en |volume=27 |issue=46 |pages=11912–11918 |doi=10.1002/chem.202101490 |pmid=34043851 |issn=0947-6539}}</ref>
	Biphenyl prevents the growth of molds and ], and is therefore used as a ] (], in combination with E231, E232 and E233), particularly in the preservation of ] fruits during transportation.
			Biphenyl occurs naturally in ], ], and ] and can be isolated from these sources via ].<ref>{{cite journal | doi = 10.1021/ac60079a020 | title = Isolation and Identification of Biphenyls from West Edmond Crude Oil | date = 1953 | last1 = Adams | first1 = N. G. | last2 = Richardson | first2 = D. M. | journal = Analytical Chemistry | volume = 25 | issue = 7 | pages = 1073–1074 }}</ref> It is produced industrially as a byproduct of the dealkylation of ] to produce ]:
	It is mildly toxic, but can be degraded biologically by conversion into nontoxic compounds. Some ] are able to hydroxylate biphenyl and its ]s (PCBs). <ref></ref>
			:{{chem2|C6H5CH3 + C6H6 -> C6H5\sC6H5 + CH4}}
			The other principal route is by the ] of ]:
			:{{chem2|2 C6H6 + ½ O2 -> C6H5\sC6H5 + H2O}}
			Annually 40,000,000&nbsp;kg are produced by these routes.<ref name=Ullmanns>{{citation | doi = 10.1002/14356007.a13_227 | chapter = Hydrocarbons | title = Ullmann's Encyclopedia of Industrial Chemistry | date = 2000 | last1 = Griesbaum | first1 = Karl | last2 = Behr | first2 = Arno | last3 = Biedenkapp | first3 = Dieter | last4 = Voges | first4 = Heinz-Werner | last5 = Garbe | first5 = Dorothea | last6 = Paetz | first6 = Christian | last7 = Collin | first7 = Gerd | last8 = Mayer | first8 = Dieter | last9 = Höke | first9 = Hartmut | isbn = 978-3-527-30385-4 }}</ref>
			In the laboratory, biphenyl can also be synthesized by treating ] with copper(II) salts.
	It is part of the active group in the antibiotic ].
			It can also be prepared using ]. When ] is treated with NaNO<sub>2</sub>+dilute HCl at 5°C, it yields benzene diazonium chloride. When this is further reacted with benzene, biphenyl is formed. This is known as the ].
			<chem>Ph-NH2-> Ph-N2+ -> Ph-Ph </chem>
			==Reactions and uses==
			Lacking functional groups, biphenyl is fairly non-reactive, which is the basis of its main application: in a ] with ], as a heat transfer agent. This mixture is stable to 400&nbsp;°C.<ref name=Ullmanns/>
			Biphenyl does undergo ] which, followed by base hydrolysis, produces ''p''-hydroxybiphenyl and ''p'',''p''′-dihydroxybiphenyl, which are useful fungicides. In other ] reactions, it undergoes halogenation. ]s were once popular pesticides.<ref name=Ullmanns/>
			===Li biphenyl radical===
			Lithium biphenyl contains the ], which is highly reducing (-3.1 V vs Fc<sup>+/0</sup>). Several solvates of alkali metal salts of biphenyl anion have been characterized by ].<ref>{{cite journal |doi=10.1039/C5NJ02841H|title=Isolation of gravimetrically quantifiable alkali metal arenides using 18-crown-6|year=2016|last1=Castillo|first1=Maximiliano|last2=Metta-Magaña|first2=Alejandro J.|last3=Fortier|first3=Skye|journal=New Journal of Chemistry|volume=40|issue=3|pages=1923–1926}}</ref> These salts, usually prepared in situ, are versatile reducing agents.<ref>{{cite journal|title=Regio- and Stereoselective Carboxylation of Allylic Barium Reagents: (E)-4,8-dimethyl-3,7-nonadienoic Acid
			|first1=Akira |last1=Yanagisawa |first2=Katsutaka |last2=Yasue |first3=Hisashi |last3=Yamamoto
			|journal=Org. Synth.|year=1997|volume=74|pages=178
			|doi=10.15227/orgsyn.074.0178}}</ref> Lithium biphenyl offers some advantages relative to the related ].<ref>{{cite journal|title=Highly Reactive Calcium for the Preparation of Organocalcium Reagents: 1-Adamantyl Calcium Halides and Their Addition to Ketones: 1-(1-Adamantyl)cyclohexanol
			|first1=Reuben D. |last1=Rieke|first2=Tse-Chong |last2=Wu|first3=Loretta I.|last3=Rieke|journal=Org. Synth.|year=1995|volume=72|page=147|doi=10.15227/orgsyn.072.0147}}</ref> Related to Li/biphenyl is the derivative with ''tert''-butyl groups on the biphenyl.<ref>{{cite journal|title=1,3-Diols from Lithium β-Lithioalkoxides Generated by The Reductive Lithiation of Epoxides: 2,5-Dimethyl-2,4-hexanediol
			|first1=Boguslaw |last1=Mudryk|first2=Theodore |last2=Cohen|journal=Org. Synth.|year=1995|volume=72|pages=173|doi=10.15227/orgsyn.072.0173}}</ref>
			==Stereochemistry==
			Rotation about the single bond in biphenyl, and especially its ] derivatives, is ]. For this reason, some substituted biphenyls show ]; that is, the individual C<sub>2</sub>-]-isomers are ]. Some derivatives, as well as related molecules such as ], find application as ]s in ]. In the case of unsubstituted biphenyl, the equilibrium torsional angle is 44.4° and the torsional barriers are quite small, 6.0 kJ/mol at 0° and 6.5 kJ/mol at 90°.<ref>{{cite journal |journal=J. Chem. Theory Comput. |doi=10.1021/ct800182e |title=Torsional Barriers and Equilibrium Angle of Biphenyl: Reconciling Theory with Experiment |year=2008 |author=Mikael P. Johansson and Jeppe Olsen |volume=4 |pages=1460–1471 |issue=9|pmid=26621432 }}</ref> Adding ortho substituents greatly increases the barrier: in the case of the 2,2'-dimethyl derivative, the barrier is 17.4 kcal/mol (72.8 kJ/mol).<ref>{{cite book |title=Stereochemistry |editor=Christoph Tamm |author=B. Testa |pages=18 |publisher=Elsevier |year=1982 |chapter=The geometry of molecules: basic principles and nomenclatures}}</ref>
	==Biphenyl compounds==		==Biphenyl compounds==
	Substituted biphenyls can be prepared synthetically by various ]s including the ] and the ] and have many uses. ]s were once used as cooling and insulating fluids and ]s are ]s. The biphenyl motif also appears in ]s such as ] and ]. The abbreviation '''E7''' stands for a ] mixture consisting of several cyanobiphenyls with long aliphatic tails used commercially in ]s. A variety of ] derivatives are used in dyes and polymers. Research into biphenyl liquid crystal candidates mainly focuses on molecules with highly polar heads (for example cyano or halide groups) and aliphatic tails.		Substituted biphenyls have many uses. They are prepared by various ]s including the ] and the ]. ]s were once used as cooling and insulating fluids and ]s are ]s. The biphenyl motif also appears in ] such as ] and ]. The abbreviation '''E7''' stands for a ] mixture consisting of several cyanobiphenyls with long aliphatic tails used commercially in ]s (], ], ] and ]<ref>{{cite journal |last1=Mouquinho |first1=Ana |last2=Saavedra |first2=Mara |last3=Maiau |first3=Alexandre |last4=Petrova |first4=Krasimira |last5=Barros |first5=M. Teresa |last6=Figueirinhas |first6=J. L. |last7=Sotomayor |first7=João |title=Films Based on New Methacrylate Monomers: Synthesis, Characterisation and Electro-Optical Properties |journal=Molecular Crystals and Liquid Crystals |date=30 June 2011 |volume=542 |issue=1 |pages=132/–140/ |doi=10.1080/15421406.2011.570154|s2cid=97514765 }}</ref>). A variety of ] derivatives are used in dyes and polymers. Research into biphenyl liquid crystal candidates mainly focuses on molecules with highly polar heads (for example cyano or halide groups) and aliphatic tails. It is part of the active group in the antibiotic ].
			==Safety and bioactivity==
	== References ==
			Biphenyl prevents the growth of ]s and ], and is therefore used as a ] (], in combination with E231, E232 and E233), particularly in the preservation of ] fruits during transportation. It is no longer approved as a food additive in the European Union.
	<references/>
	*''Biphenyl (1,1- Biphenyl)''. Wiley/VCH, Weinheim (1991), ISBN 3-527-28277-7
			Biphenyl is mildly toxic, but can be degraded biologically by conversion into nontoxic compounds. Some ] are able to hydroxylate biphenyl and its ]s (PCBs).<ref>{{cite web|url=http://www.genome.jp/dbget-bin/show_pathway?sco00621+SCO6442|title=''Biphenyl degradation - Streptomyces coelicolor'', at GenomeNet Database|work=genome.jp}}</ref>
	==See also==		==See also==
	*] where the rings are fused.		* ], where the rings are fused
			* ], three ringed analog
	*] contains two more hydrogen atoms than biphenyl.
			* ]
			* ]
			==Notes==
			{{Reflist}}
			==References==
			* "Isolation and Identification of Biphenyls from West Edmond Crude Oil". N. G. Adams and D. M. Richardson. ''Analytical Chemistry'' 1953 25 (7), 1073–1074.
			* ''Biphenyl (1,1-Biphenyl)''. Wiley/VCH, Weinheim (1991), {{ISBN|3-527-28277-7}}.
	==External links==		==External links==
	*{{ICSC|0106|01}}		*{{ICSC|0106|01}}
			*
	*{{ecb}}
	*		*
	*		*
			{{Citrus}}
			{{Aryl hydrocarbon receptor modulators}}
			{{Authority control}}
	]		]
	]		]
			]
	]
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	]
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