Imidazole-1-sulfonyl Azide on:
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Imidazole-1-sulfonyl azide is an organic
This reaction is effectively the reverse of the
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 ...
compound that can be used as an alternative 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 ...
reagent to trifluoromethanesulfonyl azide
Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis.
Preparation
Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in ...
. It is an explosive colorless liquid, but some of its organic-soluble salts can be safely handled and stored as a solid.
Preparation
The hydrochloride salt of this compound is also available commercially, but can degrade to release explosive byproducts. :
Reactions
Liketrifluoromethanesulfonyl azide
Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis.
Preparation
Trifluoromethanesulfonyl azide is prepared by treating trifluoromethanesulfonic anhydride with sodium azide, traditionally in ...
, this compound generally converts primary amines or ammonium salts to azides when catalyzed by copper(II), nickel(II), zinc(II), and cobalt(II) salts.This reaction is effectively the reverse of the
Staudinger reaction
The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry:
:R3P + R ...
. Similarly, it is able to transfer the diazo
In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds ...
group (=N2) under basic conditions.
Safety
As with all organic azides, this compound is potentially explosive both in use and in preparation. The hydrochloride salt was initially reported to be insensitive to impact, vigorous grinding, and prolonged heating at 80 °C, although heating above 150 °C resulted in violent decomposition. Further reported impact studies indicated otherwise, showing the sensitivity to be similar toRDX
RDX (Research Department Explosive or Royal Demolition Explosive) or hexogen, among other names, is an organic compound with the formula (CH2N2O2)3. It is white, odorless, and tasteless, widely used as an explosive. Chemically, it is classified ...
. Subsequent reports noted that the hydrochloride salt is hygroscopic
Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption (chemistry), absorption or adsorption from the surrounding Natural environment, environment, which is usually at normal or room temperature. If water mol ...
, and upon prolonged storage was hydrolyzed to produce hydrazoic acid
Hydrazoic acid, also known as hydrogen azide, azic acid or azoimide, This also contains a detailed description of the contemporaneous production process. is a compound with the chemical formula . It is a colorless, volatile, and explosive liquid ...
, which made the material sensitive. Synthesis of the HCl salt has led to a significant explosion, with expected explosive byproducts of sulfonyl diazide or hydrazoic acid being present.
Recent studies have shown the hydrogen sulfate salt to be significantly less hazardous to handle with decomposition temperature of 131 °C, insensitivity to impact, and low electrostatic discharge and friction sensitivities. Further improvements have led to its synthesis with increased safety, making the hydrogen sulfate salt a relatively safe diazo-transfer reagent to both synthesize and handle.{{Cite journal, last1=Potter, first1=Garrett T., last2=Jayson, first2=Gordon C., last3=Miller, first3=Gavin J., last4=Gardiner, first4=John M., date=2016-03-29, title=An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate, journal=The Journal of Organic Chemistry, language=EN, doi=10.1021/acs.joc.6b00177, volume=81, issue=8, pages=3443–3446, pmid=26998999, url=https://www.research.manchester.ac.uk/portal/files/33083992/JOC_note_jo_2016_00177a.pdf, doi-access=free
References