2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate
• CAS No.: 1001067-09-9
• Molecular Formula: C₈H₁₄N₄O₄Si
• Molecular Weight: 258.309
• Mol file: 1001067-09-9.mol

Synonyms:2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate

Chemical Property of 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate

Chemical Property:

• Solubility.: Sol organics (CH2Cl2, THF, CH3CN, EtOAc); reacts with amines.

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(Trimethylsilyl)ethyl 3-Nitro-1H-1,2,4-triazole-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Physical properties: Mp (dec.) 85–86 °C.
• Uses: 2-(Trimethylsilyl)ethoxycarbonyl (Teoc) group is one of the most useful protecting groups for amines, which can be cleaved by fluoride ion under neutral conditions. However, 2-(trimethylsilyl)ethyl chloroformate(Teoc-Cl), which is generally used for the introduction of the Teoc protecting group in amines, is quite unstable and easy to decompose; therefore, distillation is recommended at regular intervals. On the other hand, Teoc-NT is a highly stable, nonhygroscopic crystalline material and can be stored for long periods without decomposition. Generally, carbamate formation proceeds quickly under neutral conditions, and highly pure carbamates are obtained without tedious column chromatographic purification. Furthermore, the coproduct 3-nitro-1,2,4-triazole (NT) can be recycled. It participates in the reactions of Reactions with Amines and Aminoalcohols, Amine Protection for Nucleosides, Reaction with Alcohols, etc.

Technology Process of 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate

There total 1 articles about 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate 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: 96.0%

2-(trimethylsilyl)-ethoxycarbonyl chloride (20160-60-5) + 3-nitro-1,2,4-triazole (24807-55-4) → 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate (1001067-09-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol7024108

Reference yield: 100.0%

4-phenyl-1-piperazine (92-54-6) + 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate (1001067-09-9) → 2-(trimethylsilyl)ethyl 4-phenylpiperazine-1-carboxylate (1001067-19-1)

Guidance literature:

In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1021/ol7024108

Reference yield: 97.0%

2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate (1001067-09-9) + (1S,2R,5S)-(+)-menthol (15356-60-2) → 2-(trimethylsilyl)ethyl (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl carbonate (1001067-31-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1021/ol7024108

upstream raw materials:

2-(trimethylsilyl)-ethoxycarbonyl chloride

3-nitro-1,2,4-triazole

Downstream raw materials:

2-(trimethylsilyl)ethyl 4-phenylpiperazine-1-carboxylate

2-(trimethylsilyl)ethyl (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl carbonate

2-(trimethylsilyl)ethyl (R)-1-phenylethylcarbamate

phenylcarbamic acid 2-trimethylsilanylethyl ester

Refernces

• 1、 Shimizu, Mamoru,Sodeoka, Mikiko. "Convenient method for the preparation of carbamates, carbonates, and thiocarbonates". . p. 5231 - 5234. Retrieved 2008/09/17.