Imidazole trifluoromethanesulfonate

Base Information

• Chemical Name: Imidazole trifluoromethanesulfonate
• CAS No.: 29727-06-8
• Molecular Formula: C3H4N2 ^.CHF3O3S
• Molecular Weight: 218.157
• Hs Code.: 2933290090
• European Community (EC) Number: 627-698-5
• DSSTox Substance ID: DTXSID80431575
• Mol file: 29727-06-8.mol

Synonyms:29727-06-8;Imidazole trifluoromethanesulfonate;Imidazole trifluoromethanesulfonate salt;1H-Imidazole trifluoromethanesulfonate;1H-imidazole;trifluoromethanesulfonic acid;1H-imidazol-1-ium;trifluoromethanesulfonate;imidazole triflate;Quininesulfatedihydrate;starbld0009602;DTXSID80431575;AMY37975;AKOS015897530;AKOS024319338;BS-49076;FT-0655912;Imidazole trifluoromethanesulfonate salt, 97%;E78064;J-017613

Chemical Property of Imidazole trifluoromethanesulfonate

Chemical Property:

• Vapor Pressure: 1.14mmHg at 25°C
• Melting Point: 189-193 °C(lit.)
• Boiling Point: 162 °C at 760 mmHg
• Flash Point: 185.8 °C
• PSA: 91.43000
• LogP: 1.88450
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 217.99729769
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

99% ^*data from raw suppliers

Imidazole trifluoromethanesulfonate salt 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=CN1.C(F)(F)(F)S(=O)(=O)O
• General Description: **IMIDAZOLE TRIFLUOROMETHANESULFONATE SALT (IMT)** is a reagent used in oligonucleotide synthesis to facilitate the deprotection of amidine-type protecting groups (e.g., dmf, dbf) under mild acidic conditions. It acts as an efficient acid source alongside 1-hydroxybenztriazole (HOBt), enabling the synthesis of 2′-O-methyl-RNA and unmodified RNA oligomers with base-labile modifications. Its role is critical for improving hybridization, base recognition, and nuclease resistance in synthetic nucleic acids, making it valuable for applications in gene therapy and RNA-based therapeutics.

Technology Process of Imidazole trifluoromethanesulfonate

There total 7 articles about Imidazole trifluoromethanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1H-imidazole (288-32-4) + methyl trifluoromethanesulfonate (333-27-7) → imidazole trifluoromethanesulfonate (29727-06-8)

Guidance literature:

In 1-Methyl-4,5-diphenyl-2[(2-oxopropyl)thio]-imidazole; dichloromethane;

Reference yield:

1H-imidazole (288-32-4) + trifluorormethanesulfonic acid (1493-13-6) → imidazole trifluoromethanesulfonate (29727-06-8)

Guidance literature:

In ethanol; Cooling with ice;

DOI:10.1039/c2cp41027c

Reference yield:

1H-imidazole (288-32-4) + trifluoromethylsulfonic anhydride (358-23-6) → imidazole trifluoromethanesulfonate (29727-06-8) + 1-(trifluoromethylsulfonyl)-1H-imidazole (29540-81-6)

Guidance literature:

In dichloromethane; at 20°C;

DOI:10.1016/S0040-4039(01)98633-2

upstream raw materials:

trifluorormethanesulfonic acid

tert-butylphenylphosphinic imidazolidide

methyl tert-butylimidazolidophosphonate

1-(Diethoxyphosphinyl)imidazole

Downstream raw materials:

6-Oktin-2-en-yltriflat

Fe(tetraphenylporphyrin)(Himidazole)2⁽¹⁺⁾*Cl^(1-)

Refernces

Oligonucleotide synthesis involving deprotection of amidine-type protecting groups for nucleobases under acidic conditions

10.1021/ol100676j

The study presents a new method for the deprotection of amidine-type protecting groups, specifically N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, on nucleobases during oligonucleotide synthesis under mild acidic conditions. The chemicals used include imidazolium triflate (IMT) and 1-hydroxybenztriazole (HOBt) for deprotection, which allowed for the efficient synthesis of 2′-O-methyl-RNA derivatives and unmodified RNA oligomers. The purpose of these chemicals was to facilitate the synthesis of RNA oligomers with base-labile groups, which are important for improving the properties of natural DNA and RNA molecules, such as hybridization, base recognition, and nuclease resistance, and have potential applications in gene therapy. The study also examined the stability of silyl-type protecting groups and the synthesis of base-labile modified oligomers, demonstrating the applicability of the new method to various RNA synthesis scenarios.

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