60144-52-7

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl 3-methoxyphenylcarbamate serves as a crucial protecting group in the synthesis of pharmaceutical compounds, ensuring the integrity and reactivity of key functional groups during the manufacturing process. Its protective role is vital for the successful synthesis of complex drug molecules.
Used in Organic Synthesis:
In the realm of organic synthesis, tert-butyl 3-methoxyphenylcarbamate is employed as a protecting agent for functional groups, facilitating the selective reactions and preventing unwanted side reactions. This contributes to the yield and purity of the final organic compounds.
Used in Environmental Applications:
Given its low environmental impact, tert-butyl 3-methoxyphenylcarbamate can be utilized in applications where chemical stability and minimal ecological footprint are required, such as in the development of eco-friendly materials and processes.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 536-90-3 m-Anisidine 
• 2398-37-0 3-methoxyphenyl bromide 
• 4248-19-5 tert-butyl carbazate 
• 1187581-97-0 C₁₇H₂₅NO₅ 
• 1239374-12-9 tert-butyl 3-methoxyphenyl(3-perfluorooctylpropoxy)carbamate 
• 34619-03-9 tert-butyldicarbonate 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 121006-57-3 5-Methoxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester 
• 136247-96-6 2-tert-Butoxycarbonylamino-4-methoxy-benzoic acid 
• 136247-94-4 N-(tert-butoxycarbonyl)-6-methoxyanthranilic acid 
• 136247-99-9 N-(tert-butoxycarbonyl)-6-methoxyanthranilamide 
• 136248-00-5 <13CO15NH2>-N-(tert-butoxycarbonyl)-6-methoxyanthranilamide 
• 194869-14-2 N-tert-butoxycarbonyl-2-iodo-3-methoxyaniline 
• 335672-28-1 tert-butyl N-(2-formyl-3-methoxyphenyl)carbamate 
• 327183-29-9 tert-butyl 2-(2-hydroxyethyl)-3-methoxyphenylcarbamate 
• 536-90-3 m-Anisidine 
• 912669-18-2 ethyl 2-(2-(tert-butoxycarbonylamino)-6-methoxyphenyl)-2-oxoacetate 
• 98991-09-4 2-iodo-3-methoxyphenylamine 
• 1448535-59-8 tert-butyl 2-iodo-3-methoxyphenyl(propionyl)carbamate 
• 1448535-68-9 (E)-tert-butyl 2-iodo-3-methoxyphenyl(prop-1-enyl)carbamate 
• 1620683-48-8 tert-butyl allyl(3-methoxyphenyl)carbamate 

Relevant academic research and scientific papers

Zelkovamycin is an OXPHOS Inhibitory Member of the Argyrin Natural Product Family

Natural products (NPs) are an important inspirational source for developing drugs and chemical probes. In 1999, the group of ōmura reported the constitutional elucidation of zelkovamycin. Although largely unrecognized so far, this NP displays structural s

Organic/inorganic Fe3O4@MCM-41@Zr-piperazine: An impressive magnetite nanocatalyst for N-Tert-Butoxycarbonylation of amines

Fe3O4@MCM-41@Zirconium magnetic nanoparticles modified with piperazine (Fe3O4@MCM-41@Zr-piperazine), as a newly reported catalyst, shows excellent catalytic activity in N-tertbutoxycarbonylation of amines under the mild and solvent-free conditions. Accordingly, different derivatives of N-tert-butylcarbamates owning diverse aliphatic, aromatic and heteroaromatic amines were prepared efficiently. Good performance of this method for the majority of used complex or acidsensitive substrates and facile separation of this nanocatalyst due to its superparamagnetic nature from the reaction mixture via an external magnetic field for several times are the most important striking features of this protocol.

Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers

The cleavage of sulfidic C-S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C-S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies have demonstrated the diversity of the reaction mechanism at work in these different reactions.

Hypoxia-Activated Anticancer Prodrug for Bioimaging, Tracking Drug Release, and Anticancer Application

A novel anticancer theranostic prodrug, FDU-DB-NO2, specifically activated by hypoxia for selective two-photon imaging hypoxia status, real-time tracking drug release, and solid tumor therapy was designed. The devised prodrug consists of an anticancer drug floxuridine (FDU), a fluorescence dye precursor 4′-(diethylamino)-1,1′-biphenyl-2-carboxylate (DB), and a hypoxic trigger 4-nitrobenzyl group. In normal cells, FDU-DB-NO2 is "locked". Whereas in tumor cells, the prodrug is "unlocked" by hypoxia and results in fluorescent dye 7-(diethylamino)coumarin (CM) generation along with FDU release. The amounts and rates of CM formation and FDU release were controlled by hypoxic status and increased with the decreasing of the O2 concentration. The hypoxic status, distribution of oxygen, and amount of FDU release in tumor cells, spheroids, and tumor tissue could be visualized by fluorescence. FDU-DB-NO2 showed high cytotoxicity against hypoxic MCF-7 and MCG-803 cell lines and no cytotoxicity against normoxic BRL-3A cells and exhibited effective inhibition on tumor growth of MCF-7-cell-inoculated xenograft nude mice. This strategy may provide a promising platform for selective two-photon imaging hypoxia status, real-time tracking drug release, and personalized solid tumor treatment.

Preparation, characterization and application of 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl) as an efficient dicationic ionic catalyst for the N-Boc protection of amines

In this work, 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl), as a novel Br?nsted acidic ionic catalyst is synthesized and characterized using a series of techniques including FT-IR, TGA, DTA, SEM, pH analysis and Hammett acidity function. This substance can significantly catalyze the N-Boc protection of amines without solvent interference at room temperature. The advantages of this manner are chemoselectivity, short reaction times, suitable yields, excellent yields of the products, without solvent interference and ease of preparation as well as reusability of the catalyst.

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles

Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.

Preparation, characterization and application of succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the N-Boc protection of amines

In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), as a novel Bronsted acidic ionic liquid is prepared and characterized by studying its FT-IR, 1H NMR, 13C NMR, mass and SEM. This reagent can be used as an efficient catalyst for the N-Boc protection of amines at room temperature and neat conditions. This new method consistently has the advantages of excellent yields and short reaction times. Further, this ionic liquid can be recovered and reused for several times. This journal is

Palladium-catalyzed γ-selective arylation of zincated Boc-allylamines

The regio- and diastereoselective arylation of Boc-protected allylamines was performed via a one-pot lithiation/transmetalation to zinc/cross-coupling sequence, through an appropriate choice of a phosphine ligand. A variety of γ-arylated products were obtained in moderate to good yield, and the products could be directly transformed into valuable γ-arylamines and β-aryl aldehydes.

Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols

A mild, efficient and eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively short reaction times, excellent yields and low cost, availability and reusability of the catalyst are the striking features of this methodology, which can be considered to be one of the best and general methods for the protection of alcohols, phenols, thiols and amines. In addition, the use of a green reagent in the above-mentioned reactions results in a reduction of environmental pollution and of the cost of the applied methods.

Iron(III)triflate as a highly efficient, recyclable and green catalyst for the N-Boc protection of amines

Iron (III) triflate was used as an efficient catalyst for N-t-butoxycarbonylation of amines with di-t-butyl dicarbonate under solvent-free conditions at room temperature. Various aliphatic, aromatic, heterocyclic amines and aminols were protected as their corresponding mono-carbamates in excellent yields and short reaction times. Only two of the 23 monocarbamates were new. No competitive side reactions such as isocyanate, urea, nor N,N-di-Boc formation were observed. The reported method is mild and has the advantages of low cost, chemoselectivity and, because no solvent is used and the catalyst can be recycled, it is classifiable as a green procedure.