查看“︁苯硼酸”︁的源代码

{{chembox
|   NameEn = Phenylboronic acid
|   ImageFile = Phenylboronic-acid-2D-skeletal.png
|   ImageSize = 150px
|   ImageName = 苯基硼酸的结构
|   ImageFile1 = Phenylboronic-acid-from-xtal-2008-3D-balls.png
|   ImageSize1 = 160px
|   ImageName1 = 苯基硼酸的球棍模型
|   ImageFile2 = Phenylboronic acid sample.jpg
|   ImageName2 = 99.98%纯度的苯硼酸（HPLC测定）
|   IUPACName = 
|   OtherNames = 苯基硼酸
| Section1 = {{Chembox Identifiers
| CASNo = 98-80-6
| CASNo_Ref = {{cascite|correct|CAS}}
|    RTECS  =  
|    UNNumber  =  
|    EINECS  =  202-701-9
|  ChemSpiderID_Ref  = {{chemspidercite|correct|chemspider}}|  ChemSpiderID  =  60191
|  PubChem  =  66827
|  InChI  =  1/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
|  InChIKey  =  HXITXNWTGFUOAU-UHFFFAOYAQ
|  DrugBank_Ref  = {{drugbankcite|correct|drugbank}}|  DrugBank  =  DB01795
|  ChEBI_Ref  = {{ebicite|correct|EBI}}|  ChEBI  =  44923
|  SMILES  =  B(c1ccccc1)(O)O
|  ChEMBL_Ref  = {{ebicite|correct|EBI}}|  ChEMBL  =  21485
|  StdInChI_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChI  =  1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H
|  StdInChIKey_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChIKey  =  HXITXNWTGFUOAU-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
|   Formula = C<sub>6</sub>H<sub>7</sub>BO<sub>2</sub>
|   MolarMass = 121.93 
|   Appearance = 白色粉末
|   Density = 
|   Solubility = 10 g/L (20℃)<ref name="chemicalbook" />
|   SolubleOther0.1 g/mL ([[甲醇]])
|   MeltingPt = 216～219&nbsp;℃
|   BoilingPt = 
|   Viscosity = 
  }}
| Section3 = {{Chembox Structure
|   MolShape = 平面型
|   Dipole = 
  }}
| Section4 = {{Chembox Thermochemistry
|   DeltaHf = 
|   Entropy = 
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS = [http://agrippina.bcs.deakin.edu.au/bcs_admin/msds/msds_docs/Phenylboronic%20acid.pdf]{{dead link|date=October 2017 |bot=InternetArchiveBot }}
|   EUHazardSymbol = {{Chembox EUHazardSymbol|Xi|Xn|N}}
|   EUIndex = 
|   RPhrases = {{R22}}, {{R36/37/38}}, {{R20/21/22}}<ref name="chemicalbook" />
|   SPhrases = {{S22}}, {{S24/25}}, {{S36/37/39}}, {{S26}}, {{S36}}<ref name="chemicalbook" />
|   NFPA-H = 
|   NFPA-F = 
|   NFPA-R = 
|   NFPA-O = 
|   FlashPt = 
  }}
| Section8 = {{Chembox Related
|   OtherAnions = 
|   OtherCations = 
|   OtherCpds = }}}}

'''苯硼酸'''（化学式：[[苯基|Ph]][[硼|B]]([[羟基|OH]])<sub>2</sub>）是一种[[有机硼酸]]，由[[硼酸]]中的一个[[羟基]]为[[苯基]]所替换而得到。

== 性质 ==
白色[[斜方]]晶体，在水和[[苯]]等溶剂中溶解度不大，易溶于[[乙醚]]和[[甲醇]]。分子为平面型，理想的[[分子对称性]]为C<sub>2v</sub>。硼原子为 sp<sup>2</sup> [[杂化]]，含有一个空的[[p轨道]]。两分子苯基硼酸通过分子间[[氢键]]形成缔合二聚体。<ref>{{cite journal
| last1= Retting
| first1= Steven J.
| last2 = Trotter
| first2= James
| year = 1977
| title = Crystal and molecular structure of phenylboronic acid, C6H5B(OH)2
| journal = Can. J. Chem.
| volume = 55
| issue = 17
| pages = 3071–3075
| pmid =
| doi = 10.1139/v77-430
| url =https://archive.org/details/sim_canadian-journal-of-chemistry_1977-09-01_55_17/page/n10
}}</ref> 

暴露在空气中或者在加热条件下，容易脱水，形成三分子的聚合物。

== 制备 ==
该试剂已商品化，各大试剂公司均有售。 实验室可通过苯基[[格氏试剂]]（如[[苯基溴化镁]]）与[[硼酸三酯]]（如[[硼酸三甲酯]]）反应来制备。<ref>{{OrgSynth | title = Benzeneboronic anhydride | author = Wahsburn, R. M.; Levens, E.; Albright, C. F.; Billig, F. A. | year = 1963 | collvol = 4 | collvolpages = 68 | prep = cv4p0068}}</ref>

:<math>\rm \ PhMgBr+ B(OMe)_3\rightarrow PhB(OMe)_2+MeOMgBr</math>
:<math>\rm \ PhB(OMe)_2+H_2O\rightarrow PhB(OH)_2+MeOH</math>

==应用 ==
用作有机合成试剂。用途有：
*[[Suzuki反应]]中的试剂。<ref>{{cite journal en| title = Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst | author = Miyaura, N.; Suzuki, A. | journal = [[J. Chem. Soc., Chem. Commun.]] | doi = 10.1039/C39790000866 | year = 1979 | pages = 866}}</ref>
*可与[[二醇]]或[[二胺]]形成环状的[[硼酸酯]]。顺式与反式环状二醇与苯基硼酸形成比例不同的硼酸酯，此性质可用于顺式和反式二醇的分离。
*用作二醇或二胺的[[保护基]]。苯基硼酸很容易与这两者发生反应，而且极易离去。该保护基在羟基的[[酯化]]、[[甲基化]]和[[硅醚化]]等反应中都比较稳定。

== 参考资料 ==
{{reflist|refs=
<ref name="chemicalbook">{{cite web
|title=Phenylboronic acid
|url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5323625.htm
|website=ChemicalBook
|accessdate=2021-07-11
|archive-date=2021-08-16
|archive-url=https://web.archive.org/web/20210816193351/https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5323625.htm
|dead-url=no
}}</ref>
}}

{{Authority control}}
[[Category:有机化学试剂]]
[[Category:有机硼酸]]
[[Category:芳香化合物]]