Abstract
<jats:p> <jats:chem-struct-wrap> <jats:chem-struct> <jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" position="anchor" xlink:href="urn:x-wiley:9780470842898:media:rn02674:nrn02674sf.001"> <jats:alt-text>6-membered ring with 2 internal double bonds, a bromine atom, a diazo group, and an oxygen atom. The diazo and oxygen are on adjacent carbons.</jats:alt-text> </jats:graphic> </jats:chem-struct> </jats:chem-struct-wrap> <jats:table-wrap position="anchor"> <jats:table frame="hsides"> <jats:col/> <jats:col/> <jats:col/> <jats:tbody> <jats:tr> <jats:td> [ <jats:italic>1071181‐30‐0</jats:italic> ] </jats:td> <jats:td> C <jats:sub>6</jats:sub> H <jats:sub>3</jats:sub> BrN <jats:sub>2</jats:sub> O </jats:td> <jats:td>(MW 197.94)</jats:td> </jats:tr> </jats:tbody> </jats:table> </jats:table-wrap> </jats:p> <jats:p> InChI = <jats:ext-link xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="inchi" xlink:href="InChI=1S/C6H3BrN2O/c7-4-1-2-6(10)5(3-4)9-8/h1-3H">1S/C6H3BrN2O/c7‐4‐1‐2‐6(10)5(3‐4)9‐8/h1‐3H</jats:ext-link> </jats:p> <jats:p> InChIKey = <jats:ext-link xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="inchi" xlink:href="InChIKey=DTNXCCVPJPAIQO-UHFFFAOYSA-N">DTNXCCVPJPAIQO‐UHFFFAOYSA‐N</jats:ext-link> </jats:p> <jats:p>(source of carbene, synthon for phenol, annulation reactions, cross‐coupling reactions, C–H arylations)</jats:p> <jats:p> <jats:list list-type="simple"> <jats:list-item> <jats:p> <jats:italic>Alternative Name:</jats:italic> 4‐bromo‐6‐diazocyclohexa‐2,4‐dienone, 5‐bromo‐2‐hydroxybenzenediazonium. </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Physical Data:</jats:italic> mp 97–98 °C. <jats:sup> <jats:bold>1</jats:bold> </jats:sup> </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Solubility:</jats:italic> soluble in common organic solvents. </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Form Supplied in:</jats:italic> Yellow solid. <jats:sup> <jats:bold>2,3</jats:bold> </jats:sup> </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Analysis of Reagent Purity:</jats:italic> 95–98% (NMR). </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Preparative Method:</jats:italic> prepared by the addition of HCl (10 equiv) to a solution of the substituted amino phenol (1.0 equiv) in ethanol at 0 °C, stirred for 10 min (eq 1). To this solution, NaNO <jats:sub>2</jats:sub> (3.0 equiv) is added slowly over a period of 10 min and stirred. The mixture was diluted, followed by the addition of ice, and then stirred. K <jats:sub>2</jats:sub> CO <jats:sub>3</jats:sub> (6.7 equiv) was slowly added to the mixture. It was then extracted with CH <jats:sub>2</jats:sub> Cl <jats:sub>2</jats:sub> . <jats:sup> <jats:bold>3</jats:bold> </jats:sup> <jats:chem-struct-wrap> <jats:chem-struct> <jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" position="anchor" xlink:href="urn:x-wiley:9780470842898:media:rn02674:nrn02674es.001"> <jats:alt-text>Diagram of a chemical reaction converting 2 amino 4 bromophenol to a diazoquinone using Na N O 2 and H Cl.</jats:alt-text> </jats:graphic> </jats:chem-struct> </jats:chem-struct-wrap> </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Purification Method:</jats:italic> no purification required. <jats:sup> <jats:bold>3</jats:bold> </jats:sup> </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Handling, Storage, and Precautions</jats:italic> : Stored at −20 °C, under dark and anhydrous conditions. Potentially explosive and sensitive to heat and light, and should be stored carefully. <jats:sup> <jats:bold>2,3</jats:bold> </jats:sup> </jats:p> </jats:list-item> </jats:list> </jats:p>