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 ...
used as a reagent in
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
.
Preparation
Trifluoromethanesulfonyl azide is prepared by treating
trifluoromethanesulfonic anhydride with
sodium azide
Sodium azide is an inorganic compound with the formula . This colorless salt is the gas-forming component in some car airbag systems. It is used for the preparation of other azide compounds. It is highly soluble in water and is acutely poisonou ...
, traditionally in
dichloromethane
Dichloromethane (DCM, methylene chloride, or methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with ...
.
However, the use of dichloromethane is avoided since it can generate highly explosive azido-chloromethane and diazidomethane. The reaction may also instead be conducted in
toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water
Water is an inorganic compound with the c ...
,
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 class ...
, or
pyridine
Pyridine is a basic (chemistry), basic heterocyclic compound, 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, weak ...
.
: (Tf = )
An alternative route starts from
imidazole-1-sulfonyl azide.
[{{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 , 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
*
Diphenylphosphoryl azide
*
Sulfuryl diazide
References
Azido compounds
Triflyl compounds
Explosive chemicals