1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole

Base Information

• Chemical Name: 1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole
• CAS No.: 113306-55-1
• Molecular Formula: C12H17 N3 O3 Si
• Molecular Weight: 279.371
• Mol file: 113306-55-1.mol

Synonyms:1H-Benzotriazole,1-[[[2-(trimethylsilyl)ethoxy]carbonyl]oxy]- (9CI); 1-[[2-(Triethylsilyl)ethoxy]carbonyloxy]benzotriazole

Chemical Property of 1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole

Chemical Property:

• Vapor Pressure: 3.09E-05mmHg at 25°C
• Refractive Index: 1.548
• Boiling Point: 355.6°C at 760 mmHg
• Flash Point: 168.9°C
• PSA: 66.24000
• Density: 1.18g/cm³
• LogP: 2.33470

Purity/Quality:

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

1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole

There total 2 articles about 1-[2-(Trimethylsilyl)ethoxycarbonyloxy]benzotriazole 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:

2-(trimethylsilyl)-ethoxycarbonyl chloride (20160-60-5) + benzotriazol-1-ol (2592-95-2) → 1-[2-(trimethylsilyl)-ethoxycarbonyl-oxy]benzotriazole (113306-55-1)

Guidance literature:

With triethylamine; In acetonitrile; Yield given; 1.) 0 deg C, 15 min; 2.) room temp., overnight;

DOI:10.1055/s-1987-27939

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → 1-[2-(trimethylsilyl)-ethoxycarbonyl-oxy]benzotriazole (113306-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / toluene / 1.) -10 to -5 deg C, 30 min; 2.) room temp., 1 h

2: triethylamine / acetonitrile / 1.) 0 deg C, 15 min; 2.) room temp., overnight

With potassium carbonate; triethylamine; In toluene; acetonitrile;

DOI:10.1055/s-1987-27939

Reference yield: 95.0%

1-[2-(trimethylsilyl)-ethoxycarbonyl-oxy]benzotriazole (113306-55-1) + D-(4-fluoro-3-nitrophenyl)glycine methyl ester (169825-21-2) → (R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester (331731-25-0)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 25 ℃; for 19h;

DOI:10.1021/ja003835i

upstream raw materials:

2-(trimethylsilyl)-ethoxycarbonyl chloride

benzotriazol-1-ol

2-(Trimethylsilyl)ethanol

Downstream raw materials:

(R)-N-trimethylsilylethoxycarbonyl-4-fluoro-3-nitrophenylalanine methyl ester

ethyl (2R,3R)-3-[(tert-butyldimethylsilyl)oxy]-2-[N-[2-trimethylsilylethoxycarbonyl]amino]-3-[(4-fluoro-3-nitro)phenyl]propionate

(2R,3R)-3-[(tert-butyldimethylsilyl)oxy]-2-[N-[2-trimethylsilylethoxycarbonyl]amino]-3-[(4-fluoro-3-nitro)phenyl]propionic acid

C₄₉H₇₅FN₄O₁₅Si₂

Refernces

• 1、 Shute, Richard E.,Rich, Daniel H.. "Synthesis and Evaluation of Novel Activated Mixed Carbonate Reagents for the Introduction of the 2-(Trimethylsilyl)ethoxycarbonyl(Teoc)-Protecting Group". . p. 346 - 349. Retrieved 2007/10/02.