Trifluoromethanesulfonyl azide or triflyl azide is an organic
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 ...
used as a reagent 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 ...
.
Preparation
Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting
trifluoromethanesulfonic anhydride
Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF3SO2)2O. It is the acid anhydride derived from triflic acid. This compound is a strong electrophile, useful for introducing the trif ...
with
sodium azide, traditionally in
dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...
.
However, use of dichloromethane should be avoided because sodium azide is known to generate highly explosive azido-chloromethane and diazidomethane in situ by nucleophilic substitution on dichloromethane.
[Cavender, C. J.; Shiner, V. J., Jr. J. Org. Chem. (1972), 37, 3567.] Moreover, the volatility of dichloromethane is a liability, as unsolvated triflyl azide is a detonation hazard.
The reaction may also be carried out in
toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...
,
acetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not clas ...
, or
pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
.
: (Tf = )
The trifluoromethanesulfonic anhydride starting material is rather expensive, and the product is explosive, and does not store well. As a result,
imidazole-1-sulfonyl azide
Imidazole-1-sulfonyl azide is an organic azide compound that can be used as an alternative to trifluoromethanesulfonyl azide. It is an explosive colorless liquid, but some of its organic-soluble salts can be safely handled and stored as a solid.
...
has been developed as an alternative.
[{{cite journal , author1=E. D. Goddard-Borger , author2=R. V. Stick , name-list-style=amp , title = An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride , journal = ]Organic Letters
''Organic Letters'' is a biweekly peer-reviewed scientific journal covering research in organic chemistry. It was established in 1999 and is published by the American Chemical Society. In 2014, the journal moved to a hybrid open access publishing ...
, volume = 9 , issue = 19 , pages = 3797–3800 , doi = 10.1021/ol701581g , pmid = 17713918 , year = 2007
Reactions
Trifluoromethanesulfonyl azide generally converts amines to azides.
See also
*
Tosyl azide
Tosyl azide is a reagent used in organic synthesis.
Uses
Tosyl azide is used for the introduction of azide and diazo functional groups. It is also used as a nitrene source and as a substrate for +2cycloaddition reactions.
Preparation
Tosyl a ...
*
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, suc ...
*
Sulfuryl diazide
References
Azido compounds
Triflyl compounds