54840-15-2

Usage

Uses

Used in Pharmaceutical Industry:
4-N-BOC-AMINOPHENOL is used as a protecting agent for amines during the solid-phase synthesis of peptides. The Boc group provides a stable and easily removable protection for the amine, enabling selective reactions and preventing unwanted side reactions.
Used in Chemical Synthesis:
4-N-BOC-AMINOPHENOL is used as a precursor to produce [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-carbamic acid tert-butyl ester at ambient temperature. This reaction requires the use of reagent imidazole and solvents dimethylformamide (DMF) and dichloromethane (CH2Cl2), which facilitate the formation of the desired product.

InChI:InChI=1/C11H15NO3/c1-11(2,3)15-10(14)12-8-4-6-9(13)7-5-8/h4-7,13H,1-3H3,(H,12,14)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 123-30-8 4-amino-phenol 
• 23197-23-1 4-hydroxyphenylhydrazine 
• 51-78-5 p-aminophenol hydrochloride 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 
• 157427-91-3 [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-carbamic acid tert-butyl ester 
• 3422-01-3 tert-butyl phenylcarbamate 
• 100-02-7 4-nitro-phenol 
• 380430-49-9 [4-(tert-butoxycarbonylamino)phenyl]boronic acid 
• 6627-89-0 tert-butyl phenyl carbonate 
• 89985-91-1 tert-butyl pyridin-2-yl carbonate 
• 159217-89-7 N-Boc-4-iodoaniline 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 224309-64-2 tert-butyl N-(4-hydroxycyclohexyl)carbamate 

Downstream Products

• 157427-91-3 [4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-carbamic acid tert-butyl ester 
• 251996-49-3 [4-(5-chloro-4-formylpyridin-3-yloxy)phenyl]carbamic acid tert-butyl ester 
• 862075-10-3 {4-[2-(4-cyano-3-iodo-phenylcarbamoyl)-2-hydroxy-propoxy]-phenyl}-carbamic acid tert-butyl ester 
• 866021-31-0 tert-butyl 4-(2-(dimethylamino)ethoxy)phenylcarbamate 
• 866021-30-9 tert-butyl ((4-(2-piperidin-1-yl)ethoxy)phenyl)carbamate 
• 883909-78-2 6-chloromethyl-2-oxo-2H-chromene-3-carboxylic acid 4-tert-butoxycarbonylamino-phenyl ester 
• 903886-67-9 [4-(5-bromothiazol-2-yloxy)phenyl]carbamic acid tert-butyl ester 
• 850218-74-5 (S)-{4-[2-(4-cyano-3-trifluoromethylphenylcarbamoyl)-2-hydroxypropoxy]phenyl}carbamic acid tert-butyl ester 
• 669700-49-6 (S)-{4-[2-hydroxy-2-(4-nitro-3-trifluoromethylphenylcarbamoyl)propoxy]phenyl}carbamic acid tert-butyl ester 
• 737795-96-9 (R)-{4-[2-hydroxy-2-(4-nitro-3-trifluoromethylphenylcarbamoyl)propoxy]phenyl}carbamic acid tert-butyl ester 
• 95932-40-4 tert-butyl (4-((tert-butoxycarbonyl)oxy)phenyl)carbamate 
• 153756-98-0 4-acetamidophenyl chloroformate 
• 153756-97-9 4-acetamidophenyl N-(5-chloro-2-hydroxyphenyl)carbamate 
• 153757-00-7 4-<(tert-butoxycarbonyl)amino>phenyl N-(5-chloro-2-hydroxyphenyl)carbamate 

Relevant academic research and scientific papers

Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids

A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3?Me2S. The PIP group is orthogonal to the O-benzyl, O-acetyl, O-t-butyldiphenylsilyl, O-methyl, O-p-methoxybenzyl, O-allyl, O-tetrahydropyranyl and N-t-butoxy carbonyl groups. The CE step was systematically studied and was found to give higher yields when the reaction was performed in the presence of silylating agents.

Synthesis of highly potent anti-inflammatory compounds (ROS inhibitors) from isonicotinic acid

In search of anti-inflammatory compounds, novel scaffolds containing isonicotinoyl motif were synthesized via an efficient strategy. The compounds were screened for their in vitro antiinflammatory activity. Remarkably high activities were observed for isonicotinates 5-6 and 8a-8b. The compound 5 exhibits an exceptional IC50 value (1.42 ± 0.1 μg/mL) with 95.9% inhibition at 25 μg/mL, which is eight folds better than the standard drug ibuprofen (11.2 ± 1.9 μg/mL). To gain an insight into the mode of action of anti-inflammatory compounds, molecular docking studies were also performed. Decisively, further development and fine tuning of these isonicotinates based scaffolds for the treatment of various aberrations is still a wide-open field of research.

Salicylaldehyde Schiff base derivative based on ureido pyrimidone, and supramolecular polymer

The invention relates to a salicylaldehyde Schiff base derivative and a supramolecular polymer, and particularly discloses a salicylaldehyde Schiff base derivative based on ureido pyrimidone, and a supramolecular polymer formed by orthogonally self-assemb

Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate

The sulfated polyborate catalyzed an efficient and chemoselective N-tert-butyloxycarbonylation of amines under ultrasonic irradiation is developed. A broad substrate scope has been demonstrated for N-Boc protection of various primary/secondary amines. It allows converting several aliphatic/aryl/heteroaryl amines, amino alcohol, aminoester, and chiral amines to their N-Boc-protected derivatives under solvent-free conditions with excellent yields. The protocol has several advantages such as easy catalyst, and product isolation, short reaction time, excellent yields, outstanding chemoselectivity, and catalyst recyclability, among others. This makes the process practicable, economical, and environmentally benign.

Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.

Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions

Nanocerium oxide mediated an efficient and green protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at ambient temperature. Various aliphatic, aromatic and heteroaromatic amines were protected using developed protocol and several functional groups such as alcohol, phenol and ester were well tolerated under these conditions. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Smart supramolecular nanofibers and nanoribbons from uniform amphiphilic azobenzene oligomers

A series of self-assembled 1D nanostructures, including straight and helix nanofibers, nanoribbons, and nanobelts, were fabricated from uniform amphiphilic azobenzene oligomers with tunable molecular weight and side chain functionality, promoted by multiple and cooperative supramolecular interactions. Additionally, the morphological transformation of the nanofibers was achieved during the photoisomerization process.

Selective hydroboration of equilibrating allylic azides

The iridium(i)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.

POLYAROMATIC UREA DERIVATIVES AND THEIR USE IN THE TREATMENT OF MUSCLE DISEASES

The current invention provides urea derivatives, in particular compounds having the core structure heteroaryl-NH-CO-NH-aryl-O- heteroaryl, for use in treating, ameliorating, delaying, curing and/ or preventing a disease or condition associated with muscle cells and/or satellite cells, such as Duchenne muscular dystrophy, Becker muscular dystrophy, cachexia or sarcopenia.