重氮盐是无色结晶固体,爆炸性很强,干燥情况下不稳定,一般不直接分离出来。它可溶于水呈中性,发生电离,水溶液具有很强的导电能力。重氮盐一個重要應用在於染料工業<ref>Klaus Hunger, Peter Mischke, Wolfgang Rieper, ''et al.'' "Azo Dyes" in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a03_245}}.</ref>,是[[有机合成|合成]][[染料]]时的重要中间体。
* 重氮盐芳环上的[[亲核芳香取代反应]]:重氮基被其他[[官能团]]([[卤素]]、[[氰基]]、[[羟基]]、[[氢]]、[[硝基]]、[[磺酸]]基等)取代。此类型的反应包括[[Sandmeyer反应]](生成溴代和氯代芳烃)、[[Gattermann反应]]、[[Gomberg-Bachmann反应]](生成[[联苯]]衍生物)、[[Schiemann反应]](生成氟代芳烃)、'''Craig合成'''(2-氨基[[吡啶]]与亚硝酸钠、[[氢溴酸]]及过量[[溴]]反应生成2-溴吡啶<ref>''A Study of the Preparation of Alpha-Pyridyl Halides from Alpha-Aminopyridine by the Diazo Reaction'' Lyman C. Craig [[J. Am. Chem. Soc.]]; '''1934'''; 56(1); 231-232. {{DOI|10.1021/ja01316a072}}</ref>)。
在銅鹽存在下,芳香重氮鹽生成芳香[[鹵代烴]]、[[酚]]或芳香[[腈]]<ref>{{cite journal | author = Traugott Sandmeyer | author-link = Traugott Sandmeyer | title = Ueber die Ersetzung der Amidgruppe durch Chlor in den aromatischen Substanzen | year = 1884 | journal = [[Berichte der deutschen chemischen Gesellschaft]] | volume = 17 | issue = 3 | pages = 1633–1635 | doi = 10.1002/cber.18840170219 | url = http://gallica.bnf.fr/ark:/12148/bpt6k90700r/f56.chemindefer | access-date = 2023-08-05 | archive-date = 2023-03-14 | archive-url = https://web.archive.org/web/20230314051736/https://gallica.bnf.fr/ark:/12148/bpt6k90700r/f56.chemindefer | dead-url = no }}</ref><ref>{{cite journal | author = Traugott Sandmeyer | title = Ueber die Ersetzung der Amid-gruppe durch Chlor, Brom und Cyan in den aromatischen Substanzen | year = 1884 | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 17 | issue = 4 | pages = 2650–2653 | doi = 10.1002/cber.188401702202 | url = http://gallica.bnf.fr/ark:/12148/bpt6k90700r/f1073.chemindefer | access-date = 2023-08-05 | archive-date = 2023-03-14 | archive-url = https://web.archive.org/web/20230314003847/https://gallica.bnf.fr/ark:/12148/bpt6k90700r/f1073.chemindefer | dead-url = no }}</ref><ref>{{cite journal | author = Ludwig Gattermann | author-link = Ludwig Gattermann | title = Untersuchungen über Diazoverbindungen | year = 1890 | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 23 | issue = 1 | pages = 1218–1228 | doi = 10.1002/cber.189002301199 | url = http://gallica.bnf.fr/ark:/12148/bpt6k90720c/f1220.chemindefer | access-date = 2023-08-05 | archive-date = 2012-03-29 | archive-url = https://web.archive.org/web/20120329132641/http://gallica.bnf.fr/ark:/12148/bpt6k90720c/f1220.chemindefer | dead-url = no }}</ref>。反應由一價銅離子催化的單電子轉移,失去一分子氮氣<ref>{{cite journal | author = J. K. Kochi | title = The Mechanism of the Sandmeyer and Meerwein Reactions | year = 1957 | journal = [[J. Am. Chem. Soc.]] | volume = 79 | issue = 11 | pages = 2942–2948 | doi = 10.1021/ja01568a066}}</ref><ref>{{cite journal | author = H. H. Hodgson | title = The Sandmeyer Reaction | year = 1947 | journal = [[Chem. Rev.]] | volume = 40 | issue = 2 | pages = 251–277 | doi = 10.1021/cr60126a003| pmid = 20291034 }}</ref><ref>{{cite journal|last1=Nonhebel|first1=D. C.|last2=Waters|first2=W. A.|title=A Study of the Mechanism of the Sandmeyer Reaction|journal=Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences|date=8 October 1957|volume=242|issue=1228|pages=16–27|doi=10.1098/rspa.1957.0150|bibcode=1957RSPSA.242...16N|s2cid=97536209}}</ref><ref name="Galli 1988">{{cite journal|last1=Galli|first1=Carlo|title=Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical|journal=Chemical Reviews|date=August 1988|volume=88|issue=5|pages=765–792|doi=10.1021/cr00087a004}}</ref>。接著-Cl、-Br、-CN或-OH基團的加入有兩個機理。一、以上基團直接轉移到芳香環上,伴隨一價銅離子的重生。二、芳香基自由基與二價銅化合物反應生成三價銅中間體,然後發生快速的[[氧化加成|還原消去]],生成產物以及一價銅催化劑<ref>{{Cite book|title=Modern physical organic chemistry|author=Anslyn, Eric V.|date=2006|publisher=University Science|others=Dougherty, Dennis A., 1952-|isbn=978-1891389313|location=Sausalito, CA|oclc=55600610}}</ref><ref>{{Cite book|title=Organic chemistry : structure and function|url=https://archive.org/details/organicchemistry0000voll_p0b1|last=C.|first=Vollhardt, K. Peter|others=Schore, Neil Eric, 1948-|isbn=9781319079451|edition= 8e|location=New York|oclc=1007924903|date = 2018-01-29}}</ref><ref>{{Cite book|title=Advanced organic chemistry. Part B, Reactions and synthesis|author=Carey, Francis A.|date=2007|publisher=Springer|others=Sundberg, Richard J., 1938-|isbn=9781601195494|edition= 5th|location=New York, NY|oclc=223941000}}</ref>。
|-
|[[Gattermann反应]]
|氯化苯基重氮鹽與[[銅]]粉、[[鹽酸]]或[[氫溴酸]]一同加熱,可以分別製備[[氯苯]]和[[溴苯]],反應由德國化學家[[路德維希·蓋特曼]]發現<ref>{{cite journal |author= L. Gattermann |title= Untersuchungen über Diazoverbindungen |journal= Berichte der Deutschen Chemischen Gesellschaft |year= 1894 |volume= 23 |issue= 1 |pages= 1218–1228 |doi= 10.1002/cber.189002301199 |url= http://gallica.bnf.fr/ark:/12148/bpt6k90720c/f1220.chemindefer |access-date= 2023-08-05 |archive-date= 2012-03-29 |archive-url= https://web.archive.org/web/20120329132641/http://gallica.bnf.fr/ark:/12148/bpt6k90720c/f1220.chemindefer |dead-url= no }}</ref>。
芳香重氮鹽加入[[氟硼酸]]生成氟硼酸重氮鹽,加熱或光照後生成[[氟代芳烴]]<ref>{{cite journal|title = Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung|author = Günther Balz, Günther Schiemann|journal = [[Chemische Berichte|Ber.]]|volume = 5|issue = 60|pages = 1186–1190|year = 1927|doi = 10.1002/cber.19270600539}}</ref><ref>Roe, A. ''Org. React.'' '''1949''', ''5'', 193.(综述)</ref>。這個反應傳統上常用於生成[[氟苯]]及其衍生物<ref>{{OrgSynth | author = Flood, D. T. | year = 1943 | title = Fluorobenzene | collvol = 2 | collvolpages = 295 | prep = CV2P0295}}</ref>,包括[[4-氟苯甲酸]]<ref>{{OrgSynth | title = ''p''-Fluorobenzoic Acid | prep = cv2p0299 | collvol = 2 | collvolpages = 299 | author1 = G. Schiemann | author2 = W. Winkelmüller | year = 1943}}</ref>。
|-
|[[Craig合成]]
|[[2-氨基吡啶]]与[[亚硝酸钠]]、[[氢溴酸]]及过量[[溴]]反应生成[[2-溴吡啶]]<ref>''A Study of the Preparation of Alpha-Pyridyl Halides from Alpha-Aminopyridine by the Diazo Reaction'' Lyman C. Craig [[J. Am. Chem. Soc.]]; '''1934'''; 56(1); 231-232. {{DOI|10.1021/ja01316a072}}</ref>。
本[[反应机理]]尚不清楚<ref>''Strategic Applications of Named Reactions in Organic Synthesis'' Laszlo Kurti, Barbara Czako Academic Press (March 4, '''2005''') ISBN 0-12-429785-4</ref>。
加熱芳香重氮鹽的水溶液,可以得到[[苯酚]]<ref>{{cite journal|author=H. E. Ungnade, E. F. Orwoll|doi=10.15227/orgsyn.023.0011|title=3-Bromo-4-hydroxytoluene|journal=[[Org. Synth.]] |volume=23|pages=11|year=1943}}</ref><ref name=":0">{{Cite journal|date=2017|title=Facile Preparation of Phenol|journal=Synlett|volume=28|issue=13|pages=1641–1645|doi=10.1055/s-0036-1588180|last1=Kazem-Rostami|first1=Masoud|s2cid=99294625 }}</ref><ref>{{Cite book|title=Advanced Organic Chemistry|url=https://archive.org/details/advancedorganicc00care_636|url-access=limited|author1=Carey, F. A. |author2=Sundberg, R. J. |publisher=Springer|year=2007|location=Vol. B, Chapter 11|pages=[https://archive.org/details/advancedorganicc00care_636/page/n1051 1028]}}</ref><ref>{{Cite journal|doi=10.1002/app.39069|title=Synthesis, characterization, and application of a triazene-based polysulfone as a dye adsorbent|journal=Journal of Applied Polymer Science|volume=129|issue=6|pages=3439–3446|year=2013|last1=Khazaei|first1=Ardeshir|last2=Kazem-Rostami|first2=Masoud|last3=Zare|first3=Abdolkarim|last4=Moosavi-Zare|first4=Ahmad Reza|last5=Sadeghpour|first5=Mahdieh|last6=Afkhami|first6=Abbas}}</ref>。化學式如下:<br/>
由於生成的苯酚有機會跟原先的重氮鹽反應,因此反應會在[[酸]]的存在下進行,以壓抑上述副反應<ref>{{cite journal|author=R. H. F. Manske|doi=10.15227/orgsyn.008.0080|title=''m''-Nitrophenol|journal=[[Org. Synth.]] |volume=8|pages=80|year=1928}}</ref>。<br/>
===還原===
用[[次磷酸]]<ref>Reinhard Bruckner, ed. Michael Harmata; Organic Mechanisms Reactions, Stereochemistry and Synthesis 3rd Ed, p.246, {{ISBN|978-3-8274-1579-0}}</ref>、[[乙醇]]<ref>{{cite journal|date=1958|title=Mechanisms of Diazonium Salt Reactions. VI. The Reactions of Diazonium Salts with Alcohols under Acidic Conditions; Evidence for Hydride Transfer1|journal=Journal of the American Chemical Society|volume=80|issue=22|pages=6072–6077|doi=10.1021/ja01555a044|last1=DeTarr|first1=D.F.|last2=Kosuge|first2=T.}}</ref>、[[硼氢化钠]]、[[氫化三丁基锡]]、[[三乙基矽烷]]在不同介質還原,重氮基被氢取代,放出[[氮氣]],生成[[苯]]。重氮化反应與该反应常用于向芳环引入[[氨基]],借助其[[定位效应]],达到目的后再将该导向基除去<ref>{{cite book |author1=邢其毅 |author2=裴偉偉 |author3=徐瑞秋 |author4=裴堅 |title=基礎有機化學978-7-301-27943-4 |publisher=北京大學出版社 |location=北京 |page=870 |edition=第四版 |accessdate=2023-08-01 |chapter=18}}</ref>。
固體鹵化重氮鹽很多時候是危險的,具有爆炸性,曾有過傷亡報告<ref name=supersat>{{cite web|url=http://www.crhf.org.uk/incident71.html|title=UK CRHF Incident Report – Supersaturated Diazonium salt causes Fatality|publisher=UK Chemical Reaction Hazards Forum|access-date=13 May 2010|archive-url=https://web.archive.org/web/20181006095115/http://www.crhf.org.uk/incident71.html|archive-date=6 October 2018|url-status=dead}}</ref>。
^Klaus Hunger, Peter Mischke, Wolfgang Rieper, et al. "Azo Dyes" in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_245.
^Filimonov, Victor D.; Trusova, Marina; Postnikov, Pavel; Krasnokutskaya, Elena A.; Lee, Young Min; Hwang, Ho Yun; Kim, Hyunuk; Chi, Ki-Whan. Unusually Stable, Versatile, and Pure Arenediazonium Tosylates: Their Preparation, Structures, and Synthetic Applicability. Organic Letters. 2008-09-18, 10 (18): 3961–3964. ISSN 1523-7060. PMID 18722457. doi:10.1021/ol8013528(英语).
^Nonhebel, D. C.; Waters, W. A. A Study of the Mechanism of the Sandmeyer Reaction. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences. 8 October 1957, 242 (1228): 16–27. Bibcode:1957RSPSA.242...16N. S2CID 97536209. doi:10.1098/rspa.1957.0150.
^Galli, Carlo. Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical. Chemical Reviews. August 1988, 88 (5): 765–792. doi:10.1021/cr00087a004.
^Anslyn, Eric V. Modern physical organic chemistry. Dougherty, Dennis A., 1952-. Sausalito, CA: University Science. 2006. ISBN 978-1891389313. OCLC 55600610.
^Carey, Francis A. Advanced organic chemistry. Part B, Reactions and synthesis. Sundberg, Richard J., 1938- 5th. New York, NY: Springer. 2007. ISBN 9781601195494. OCLC 223941000.
^March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7.
^Günther Balz, Günther Schiemann. Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung. Ber. 1927, 5 (60): 1186–1190. doi:10.1002/cber.19270600539.
^A Study of the Preparation of Alpha-Pyridyl Halides from Alpha-Aminopyridine by the Diazo Reaction Lyman C. Craig J. Am. Chem. Soc.; 1934; 56(1); 231-232. doi:10.1021/ja01316a072
^Minireview Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts Markus R. Heinrich doi:10.1002/chem.200801306 Chemistry - A European Journal 2008 Volume 15 Issue 4, Pages 820 - 833
^Strategic Applications of Named Reactions in Organic Synthesis Laszlo Kurti, Barbara Czako Academic Press (March 4, 2005) ISBN 0-12-429785-4
^Hassner, A., Stumer, C., Organic Synthesis Based on Name Reactions: 2nd. Ed. Tetrahedron Organic Chemistry Series, Volume 22 Pergamon, Oxford ISBN0-08-043260-3
^Khazaei, Ardeshir; Kazem-Rostami, Masoud; Zare, Abdolkarim; Moosavi-Zare, Ahmad Reza; Sadeghpour, Mahdieh; Afkhami, Abbas. Synthesis, characterization, and application of a triazene-based polysulfone as a dye adsorbent. Journal of Applied Polymer Science. 2013, 129 (6): 3439–3446. doi:10.1002/app.39069.
^Reinhard Bruckner, ed. Michael Harmata; Organic Mechanisms Reactions, Stereochemistry and Synthesis 3rd Ed, p.246, ISBN978-3-8274-1579-0
^DeTarr, D.F.; Kosuge, T. Mechanisms of Diazonium Salt Reactions. VI. The Reactions of Diazonium Salts with Alcohols under Acidic Conditions; Evidence for Hydride Transfer1. Journal of the American Chemical Society. 1958, 80 (22): 6072–6077. doi:10.1021/ja01555a044.