View source for Benzotriazole

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| verifiedrevid = 271892757
| ImageFile = Benzotriazole_-_numbered.png
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| IUPACName = 
| OtherNames = 1H-Benzotriazol, 1,2,3-Benzotriazol, btaH
| Section1 = {{Chembox Identifiers
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| CASNo = 95-14-7
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| PubChem = 7220
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| Section2 = {{Chembox Properties
|C=6|H=5|N=3
| Appearance = solid
| Density = 1,36 g·cm<sup>−3</sup>&nbsp;<ref name="Merck">''[http://de.chemdat.info/mda/de chemdat.info]''</ref>
| MeltingPt = 100 °C&nbsp;<ref name="SRC">SRC PhysProp Database: ''[http://esc.syrres.com/interkow/webprop.exe?CAS=95-14-7 1H-Benzotriazole]''</ref>
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| BoilingPt = 350 °C&nbsp;<ref name="SRC"/>
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| Solubility = soluble in water (20 g/l)&nbsp;<ref name="SRC"/>
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| pKa = 8,37&nbsp;<ref name="SRC"/>
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| Section6 = {{Chembox Explosive
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| Section7 = {{Chembox Hazards
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| MainHazards = XN&nbsp;<ref name="Merck"/>
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| RPhrases = {{R20/22}} {{R36}} {{R52/53}}&nbsp;<ref name="Merck"/>
| SPhrases = –
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| Section8 = {{Chembox Related
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| OtherCpds = [[Benzimidazole]]}}
}}

'''Benzotriazole''' is a [[heterocyclic compound]] with the formula C<sub>6</sub>H<sub>4</sub>N<sub>3</sub>H. This [[aromatic compound|aromatic]] is a commonly used corrosion inhibitor.  It is a colourless solid that is soluble in polar solvents, including water. Benzotriazoles are also a class of compounds containing the benzotriazole skeleton.

==Structure and synthesis==
Benzotriazole is classified as an 1,2,3-[[triazole]], i.e. a cyclic compound with the linkage -N=N-NH-. Benzotriazole features two fused rings. 

Benzotriazole is produced by reaction of [[o-phenylenediamine]], [[sodium nitrite]] and [[acetic acid]].  The conversion proceeds via [[diazotization]] of one of the amine groups.<ref name=Ullmann>Robert A. Smiley “Phenylene- and Toluenediamines” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a19_405}}</ref>
[[File:Benzotriazol synthesis.png|600px]]

== Uses ==
Benzotriazole is a [[complexing agent]] and as such is a useful a [[corrosion inhibitor]], e.g. for silver protection in [[dishwashing detergent]]s and an anti-fog agent in photographic development. [[Deicing fluid|Aircraft deicer]] and [[Ice protection system|anti-icer fluid]] contain benzotriazole.  Benzotriazole derivatives are found in [[pharmaceuticals]] such as [[antifungal]], [[antibacterial]], and [[anthelmintic]] drugs.

== Environmental relevance ==
Benzotriazole is fairly water-soluble, not readily degradable and has a limited sorption tendency. Hence, it is only partly removed in [[wastewater treatment plant]]s and a substantial fraction reaches surface water such as rivers and lakes.<ref>W. Giger, C. Schaffner, HP. Kohler (2006): ''Benzotriazole and Tolyltriazole as Aquatic Contaminants. 1. Input and Occurrence in Rivers and Lakes''. Environ. Sci. Technol. 40,7186-7192. PMID 17180965</ref>

== References ==
<references/>

[[Category:Corrosion inhibitors]]
[[Category:Chelating agents]]
[[Category:Benzotriazoles]]

[[de:Benzotriazol]]
[[fr:Benzotriazole]]
[[it:1H-benzotriazolo]]
[[lv:Benztriazols]]
[[nl:Benzotriazool]]
[[ru:Бензотриазол]]
[[zh:苯并三唑]]
[[Category:2Fix]]