130384-98-4

Basic information

• Product Name: N-Boc-Benzotriazole
• Synonyms: AKOS 39;N-BUTOXYCARBONYLBENZOTRIAZOLE;N-BOC-BENZOTRIAZOLE;1-(TERT-BUTOXYCARBONYL)BENZOTRIAZOLE;1-(T-BUTOXYCARBONYL)BENZOTRIAZOLE;tert-Butyl 1H-benzo[d][1,2,3]triazole-1-carboxylate
• CAS NO: 130384-98-4
• Molecular Formula: C₁₁H₁₃N₃O₂
• Molecular Weight: 219.24
• Mol File: 130384-98-4.mol

Chemical Properties

• Boiling Point: 324.405 °C at 760 mmHg
• Flash Point: 149.995 °C
• Appearance: /
• Density: 1.222 g/cm³
• Vapor Pressure: 0.000246mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: N-Boc-Benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-Benzotriazole(130384-98-4)
• EPA Substance Registry System: N-Boc-Benzotriazole(130384-98-4)

Safety Data

• Hazardous Substances Data: 130384-98-4(Hazardous Substances Data)

Usage

Uses

Used in Polymer Industry:
N-Boc-Benzotriazole is used as a photoinitiator for the production of photopolymers, facilitating the polymerization process upon exposure to UV radiation. Its ability to initiate reactions in polymerization processes is crucial for the creation of materials with specific properties tailored for various applications.
Used in Stabilizer Applications:
As a stabilizer for polymers, N-Boc-Benzotriazole helps to prevent degradation and maintain the integrity of polymers, thereby extending their shelf life and improving their performance in end-use applications.
Used in Peptide Synthesis:
N-Boc-Benzotriazole is utilized as an inhibitor in the synthesis of peptides, playing a critical role in controlling the reaction conditions and ensuring the desired peptide product is obtained without unwanted side reactions.
Used in Organic Chemistry:
In the realm of organic chemistry, N-Boc-Benzotriazole serves as a reagent, contributing to a wide range of chemical reactions and synthesis pathways, thereby expanding the scope of chemical research and development.
Used in Industrial Applications:
Due to its low volatility and high thermal stability, N-Boc-Benzotriazole is employed across various industries where these properties are advantageous, such as in the production of coatings, adhesives, and other materials that require specific curing and performance characteristics.

InChI:InChI=1/C11H13N3O2/c1-11(2,3)16-10(15)14-9-7-5-4-6-8(9)12-13-14/h4-7H,1-3H3

Upstream product

• 65095-13-8 1-benzotriazolecarboxylic acid chloride 
• 75-65-0 tert-butyl alcohol 
• 95-14-7 1,2,3-Benzotriazole 
• 34619-03-9 tert-butyldicarbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 95-54-5 1,2-diamino-benzene 
• 146651-75-4 tert–butyl (2–aminophenyl)carbamate 

Downstream Products

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 21887-64-9 N₂-(tert-butoxycarbonyl)-L-ornithine 
• 2389-60-8 Z-Lys(Boc)-OH 
• 95-14-7 1,2,3-Benzotriazole 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 2488-15-5 N-tert-butoxycarbonyl-L-methionine 
• 4530-20-5 BOC-glycine 
• 13139-14-5 Boc-Trp-OH 
• 1385775-56-3 N-Boc-L-Cys(S-(4-NO₂-Bz))-OH 

Relevant articles and documents

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids

Stable Fmoc-, Boc-, and Alloc-benzotriazoles react with various amino acids including unprotected serine and glutamic acid, in the presence of triethylamine at 20° as reagents to introduce -amino protecting groups to afford Fmoc-, Boc-, and Alloc-protected amino acids (77-94%) free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in 90% yields by N-acylation of glycylglycine with Fmoc- and Alloc-benzotriazoles in the presence of triethylamine. Synthesized N-protected amino acids were greater than 99% pure, analyzed by HPLC. Georg Thieme Verlag Stuttgart - New York.

PROCESS FOR THE PREPARATION OF ε-ALKOXYCARBONYLLYSINES AND THEIR ANALOGUES

A process for the preparation of ω-alkoxycarbonylamino-α-aminoacids and α,ω orthogonally diprotected diaminoacids from α,ω-diaminoacids using 1- alkoxycarbonylbenzotriazoles as protecting agents is disclosed. In an alternative embodiment, carbamoylating agents in the presence of benzotriazoles are used instead of 1-alkoxycarbonylbenzotriazoles. This reaction is preferably applied to the preparation of ε- alkoxycarbonyllysines from lysine. A process for the preparation of t-butoxycarbonylbenzotriazoles and novel complexes of ω-alkoxycarbonylamino-α-aminoacids with benzotriazoles are also disclosed.

Synthesis of 1-(t-butoxycarbonyl)benzotriazole and 1-(p-methoxybenzyloxycarbonyl)benzotriazole and their use in the protection of amino acids

Benzotriazol-1-ylcarbonyl chloride, generated from benzotriazole and phosgene, reacts with t-butyl alcohol and p-methoxybenzyl alcohol to give 1-(t-butoxycarbonyl)benzotriazole (4) and 1-(p-methoxybenzyloxycarbonyl)benzotriazole (5), respectively in good yields. The synthetic utility of ragents 4 and 5 is shown by effective amino protection in phenylalanine and phenylglycine.