20444-09-1

Basic information

• Product Name: 2-Nitrobenzyl p-toluenesulfonate
• Synonyms: 2-Nitrobenzyl p-toluenesulfonate
• CAS NO: 20444-09-1
• Molecular Formula: C₁₄H₁₃NO₅S
• Molecular Weight: 307.32
• Mol File: 20444-09-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Nitrobenzyl p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrobenzyl p-toluenesulfonate(20444-09-1)
• EPA Substance Registry System: 2-Nitrobenzyl p-toluenesulfonate(20444-09-1)

Safety Data

• Hazardous Substances Data: 20444-09-1(Hazardous Substances Data)

Usage

Description

2-Nitrobenzyl p-toluenesulfonate is a chemical compound derived from p-toluenesulfonic acid and 2-nitrobenzyl alcohol, commonly utilized in organic synthesis and as a protecting group in peptide chemistry. It is known for its selective protection of hydroxyl groups in organic reactions, making it a versatile reagent for the preparation of various organic compounds, including pharmaceutical intermediates and agrochemicals.

Uses

Used in Organic Synthesis:
2-Nitrobenzyl p-toluenesulfonate is used as a reagent for the selective protection of hydroxyl groups in organic reactions, facilitating the synthesis of a wide range of organic compounds.
Used in Peptide Chemistry:
In peptide chemistry, 2-Nitrobenzyl p-toluenesulfonate serves as a protecting group, enabling the controlled formation of peptide bonds and the synthesis of complex peptide structures.
Used in Pharmaceutical Intermediates:
2-Nitrobenzyl p-toluenesulfonate is used as a key component in the synthesis of pharmaceutical intermediates, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemicals:
2-Nitrobenzyl p-toluenesulfonate is also utilized in the synthesis of agrochemicals, playing a role in the development of pesticides and other agricultural chemicals.
Used in Prodrug and Biologically Active Molecule Synthesis:
2-Nitrobenzyl p-toluenesulfonate has been employed in the synthesis of prodrugs and other biologically active molecules, making it a valuable tool in chemical research and drug development.

Upstream product

• 612-25-9 2-Nitrobenzyl alcohol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 612-25-9 2-Nitrobenzyl alcohol 
• 29809-25-4 2-nitrosobenzaldehyde 
• 104-15-4 toluene-4-sulfonic acid 
• 858343-03-0 C₃₅H₂₂N₂O₁₁ 
• 529-23-7 o-aminobenzaldehyde 

Relevant articles and documents

Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water

A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.

Photocleavage of o-nitrobenzyl ether derivatives for rapid biomedical release applications

The externally controlled cleavage of covalently linked prodrugs, proteins, or solid-phase formulation vehicles offers potential advantages for controlled drug or gene delivery. A series of o-nitrobenzyl ester compounds (1-8) were synthesized to allow a systematic study of photolability. The o-nitrobenzyl ester was strictly required for photolability, while imido esters were not photolabile. The degradation kinetics of 1-o-phenylethyl ester was an order of magnitude faster than that of o-nitrobenzyl ester. Tosylate, phosphate, and benzoate derivatives of 1-o-nitrophenylethyl displayed similar photolability (>80% decomposition within 10 min at 3.5 mW/cm2 at 365 nm). O-o-Nitrobenzyl O′,O″-diethyl phosphate displayed the fastest decomposition at photoirradiation condition (3.5 mW/cm2, 365 nm) suitable for biological systems. We report the synthesis and photo-decomposition of 1-o-nitrophenylethyl derivatives amenable for the creation of photolabile prodrugs or formulation particles for drug depots, DNA condensation, or tissue engineering applications.

Cell-permeable small molecule probes for site-specific labeling of proteins.

We have successfully synthesized a number of small molecule probes designed for site-specific labeling of N-terminal cysteine-containing proteins expressed in live cells. Their utility for site-specific, covalent modifications of proteins was successfully demonstrated with purified proteins in vitro, and with live bacterial cells in vivo.