reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
used in
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
.
Uses
Tosyl azide is used for the introduction of
azide
In chemistry, azide is a linear, polyatomic anion with the formula and structure . It is the conjugate base of hydrazoic acid . Organic azides are organic compounds with the formula , containing the azide functional group. The dominant applic ...
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
s. It is also used as a
nitrene
In chemistry, a nitrene or imene () is the nitrogen analogue of a carbene. The nitrogen atom is uncharged and univalent, so it has only 6 electrons in its valence level—two covalent bonded and four non-bonded electrons. It is therefore consid ...
source and as a substrate for +2cycloaddition reactions.
Preparation
Tosyl azide can be prepared by the reaction of
tosyl chloride
4-Toluenesulfonyl chloride (''p''-toluenesulfonyl chloride, toluene-''p''-sulfonyl chloride) is an organic compound with the formula CH3C6H4SO2Cl. This white, malodorous solid is a reagent widely used in organic synthesis. Abbreviated TsCl or ...
acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
.
Safety
Tosyl azide is one of the most stable azide compounds but is still regarded as a potential explosive and should be carefully stored, while particular caution is vital for all reactions in which it is heated at or above 100 °C. The initial temperature of the explosive decomposition is about 120 °C.
See also
*
Diphenylphosphoryl azide
Diphenylphosphoryl azide (DPPA) is an organic compound. It is widely used as a reagent in the synthesis of other organic compounds.
Uses
DPPA undergoes pseudohalogen replacement of the azido group by treatment with nucleophilic reagents, such ...
*
Trifluoromethanesulfonyl azide
Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis.
Preparation
Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting trifluoromethanesulfoni ...