Imidazole-1-sulfonyl azide hydrochloride

• CAS: 952234-36-5
• Catalog Number: ACM952234365
• Category: Main Products
• Molecular Weight: 209.61
• Molecular Formula: C3H3N5O2S·HCl
• Melting Point: 99-104°C
• Appearance: Solid
• Application: Imidazole-1-sulfonyl azide hydrochloride is a versatile azide salt that serves as a crucial intermediate in organic synthesis and material chemistry. It is widely utilized as a diazotropic transfer reagent in chemical synthesis and plays a pivotal role in the creation of bioactive molecules and organic functional materials.

Case Study

Perform diazo transfer reaction using imidazole-1-sulfonyl azide hydrochloride

Lartia, Rémy, et al. Current Protocols in Nucleic Acid Chemistry 50.1 (2012): 4-50.

Using diazo transfer reagent, imidazole-1-sulfonyl azide hydrochloride (ISAHC), in the presence of copper cations, clean and efficient aminated oligodeoxyribonucleotides (ODN) are converted to azide counterparts under mild conditions. ODNs with amino chains at positions 3, 5, or any internal position can be modified in this way, demonstrating the multifunctionality of the reaction. This method also benefits from commercial availability or is easily obtained through conventional automated DNA synthesis using amino containing oligodeoxyribonucleotide starting materials. It is of great interest to easily obtain ODNs modified with azide groups, especially for copper catalyzed 1,3-dipolar cycloaddition (CuAAC reaction) conjugation.
Dissolve 50 nmol of dry amino alkyl ODN in 200 μ L of 50 mM NaHCO buffer (pH=8.5)/MeOH (3:1) solution to prepare ODN solution (Solution A), and transfer it to a closed screw cap plastic vial. Vortex for 1 minute. Add 2 μ L of CuSO solution. Vortex for 1 minute. Dissolve 25 mg of ISAHC in 1 mL of water/MeOH (1:1; v/v) solution and prepare a fresh ISAHC solution (solution B). Add 10 μ L of solution B to ODN solution A. Vortex for 1 minute, then heat the small bottle at 60 ℃ for 2 hours. Cool the small bottle at room temperature. Add 100 μ L TEAA solution to quench the reaction mixture. According to the required purity, purify the azide ODN using a spatial exclusion column according to the manufacturer's recommendations (actual details are provided in Basic Scheme 3) or by using preparative HPLC.

One pot synthesis of triazole using imidazole-1-sulfonyl azide hydrochloride

Smith, Neal M., et al. Synlett 2009.09 (2009): 1391-1394.

A practical and efficient one pot method for the selective synthesis of functionalized 1,4-disubstituted 1,2,3-triazoles from primary amines and terminal acetylenes was established using the inexpensive and stable diazo transfer reagent imidazole-1-sulfonylazide hydrochloride. A one-step synthesis program for 1,2,3-triazoles has been developed from different ranges of primary amines and terminal acetylenes. This method is simple to experiment with and suitable for parallel chemistry. This surgery avoids safety issues associated with early surgery. A wide range of amines are commercially available, making this method widely applicable in the pharmaceutical industry.
Optimize the reaction conditions of one pot method using standard reaction between phenylacetylene and benzylamine in the presence of imidazole-1-sulfonylazide hydrochloride. Usually, the reaction is carried out using 10 mol% copper (II) sulfate and 20 mol% sodium ascorbate. Stir the reactants at room temperature for 20 hours, evaporate the reaction mixture, and purify the product by preparative HPLC or column chromatography. Studies using standard reactions have shown that potassium carbonate can be replaced by organic bases such as triethylamine or diisopropylethylamine. These changes allow for the removal of water from the reaction medium, which was initially added to aid in the dissolution of potassium carbonate and copper salts. There is no adverse effect on the yield. When carried out in methanol and ethanol, the standard reaction effectively proceeds, forming 1-benzyl-4-phenyl-1H-1,2,3-triazole with separation yields of 90% and 97%, respectively. Removing water from the reaction medium allows for the evaluation of other solvents. A series of solvents were screened in the standard reaction, and methanol and ethanol were identified as the optimal solvents. Polyazoles such as TBTA have been identified as copper (I) stable ligands. Beckmann used TBTA in his initial one pot method. During the optimization study, it was shown that adding TBTA did not provide any additional benefits. The most significant effect is observed when the reaction is carried out in the absence of an inert nitrogen atmosphere. The yield of separation significantly decreased, and it is speculated that this is due to the oxidation of Cu (I) catalyst to Cu (II) by atmospheric oxygen, thereby closing the Cu (I) - mediated catalytic cycle.

A new diazo transfer reagent - imidazole-1-sulfonyl azide hydrochloride

Goddard-Borger, Ethan D., and Robert V. Stick. Organic letters 9.19 (2007): 3797-3800.

A new diazo transfer reagent, imidazole-1-sulfonyl azide hydrochloride, is reported. The reagent is shown to be comparable to triflate azide in its ability to act as a "diazo donor" in the conversion of primary amines to azides and in the conversion of activated methylene substrates to diazo compounds. Crucially, the reagent can be prepared in large scale using inexpensive materials in a one-pot reaction, is storage stable, and can be conveniently crystallized.
In a typical experiment, imidazole-1-sulfonyl azide hydrochloride (1.2 mmol) was added to an amine or its hydrochloride (1.0 mmol), potassium carbonate (2.0 mmol), and copper (II) sulfate pentahydrate (10 μmol, 1 mol%) in methanol (5 mL). After completion of the reaction (TLC), the mixture was concentrated. For non-carbohydrate substrates (entries 3-13), workup and flash chromatography afforded the corresponding azides. For carbohydrate substrates, acetic anhydride (8 mmol) was added to the residue in pyridine (5 mL). After the reaction was complete (TLC), the mixture was concentrated; workup and flash chromatography then gave the corresponding peracetylated azide. This value is available for the comparable reaction with TfN 3 . The product is volatile, resulting in a reduced yield. This literature value was obtained using 15 mol % of Cucatalyst, not the 1 mol % used here.

Imidazole-1-sulfonyl azide hydrochloride for the study of new azide transfer reagents

Okumu, Antony A. MS thesis. Youngstown State University, 2010.

Traditionally, sodium azide has been used as the source of azide anions for the synthesis of alkyl azides. In addition to solubility issues, sodium azide is toxic, can be absorbed through the skin, and forms explosive compounds with H2O, Brønsted acids, CH2Cl2, and CHCl3. To avoid these hazards, a new azide transfer reagent was developed, which was prepared by the reaction of 4-acetamidobenzenesulfonyl azide (p-ABSA) and 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU). It is much safer than sodium azide and can be used to synthesize alkyl and acyl azides. The alkyl azide thus obtained was used to attempt the in situ generation of 1,2,3-triazole, an aromatic five-membered heterocycle with two carbon atoms and three nitrogen atoms, which is of great biological importance. The synthesis of 1,2,3-triazoles was compared with imidazole-1-sulfonyl azide hydrochloride.
1,4-Disubstituted-1,2,3-triazoles have been synthesized from primary amines and terminal acetylenes using the inexpensive, shelf-stable diazo transfer reagent imidazole-1-sulfonyl azide hydrochloride. The procedure begins with the formation of the azide from primary amines and trifluoromethanesulfonic acid azide in the presence of copper(II) sulfate and solid sodium bicarbonate. The terminal acetylene is then added along with sodium ascorbate and the copper(I)-stabilized ligand tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-amine (TBTA). Finally, microwave heating is performed for the azide-acetylene dipolar cycloaddition.

Custom Q&A

What is the molecular formula of Imidazole-1-sulfonyl azide hydrochloride?

The molecular formula of Imidazole-1-sulfonyl azide hydrochloride is C3H4ClN5O2S.

What are the synonyms of Imidazole-1-sulfonyl azide hydrochloride?

The synonyms of Imidazole-1-sulfonyl azide hydrochloride include N-diazoimidazole-1-sulfonamide; hydrochloride, N-diazoimidazole-1-sulfonamide hydrochloride, Imidazole-1-sulfonyl azide, and more.

What is the IUPAC name for Imidazole-1-sulfonyl azide hydrochloride?

The IUPAC name for Imidazole-1-sulfonyl azide hydrochloride is N-diazoimidazole-1-sulfonamide; hydrochloride.

What is the InChI of Imidazole-1-sulfonyl azide hydrochloride?

The InChI of Imidazole-1-sulfonyl azide hydrochloride is InChI=1S/C3H3N5O2S.ClH/c4-6-7-11(9,10)8-2-1-5-3-8;/h1-3H;1H.

What is the InChIKey of Imidazole-1-sulfonyl azide hydrochloride?

The InChIKey of Imidazole-1-sulfonyl azide hydrochloride is XYURSCOGYWBRDR-UHFFFAOYSA-N.

What is the molecular weight of Imidazole-1-sulfonyl azide hydrochloride?

The molecular weight of Imidazole-1-sulfonyl azide hydrochloride is 209.62g/mol.

How many hydrogen bond donor counts are there in Imidazole-1-sulfonyl azide hydrochloride?

There is 1 hydrogen bond donor count in Imidazole-1-sulfonyl azide hydrochloride.

How many hydrogen bond acceptor counts are there in Imidazole-1-sulfonyl azide hydrochloride?

There are 5 hydrogen bond acceptor counts in Imidazole-1-sulfonyl azide hydrochloride.

How many rotatable bond counts are there in Imidazole-1-sulfonyl azide hydrochloride?

There are 2 rotatable bond counts in Imidazole-1-sulfonyl azide hydrochloride.

Is Imidazole-1-sulfonyl azide hydrochloride a canonicalized compound?

Yes, Imidazole-1-sulfonyl azide hydrochloride is a canonicalized compound.