131818-17-2

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its reactivity in Suzuki coupling reactions allows for the formation of biaryls, which are important structural motifs in many drug molecules.
Used in Chemical Synthesis:
TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE is used as a starting material for the synthesis of various organic compounds. Its BOC protection group can be selectively removed under mild conditions, allowing for further functionalization and modification of the molecule.
Used in Research and Development:
TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE is used as a research compound in the development of new synthetic methods and reaction conditions. Its unique reactivity and protecting group make it a valuable tool for exploring new chemical transformations and applications.

InChI:InChI=1/C11H14BrNO2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h4-7H,1-3H3,(H,13,14)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 106-40-1 4-bromo-aniline 
• 193533-92-5 4-methyl-1,2,3-trifluorobenzene 
• 540-37-4 p-aminoiodobenzene 
• 1239374-02-7 tert-butyl 4-bromophenyl(3-perfluorooctylpropoxy)carbamate 
• 586-76-5 4-Bromobenzoic acid 
• 75-65-0 tert-butyl alcohol 
• 4248-19-5 tert-butyl carbazate 
• 589-87-7 1,4-bromoiodobenzene 
• 2617-78-9 N-(4-bromophenyl)formamide 
• 2493-02-9 4-bromophenyl isocyanate 
• 3422-01-3 tert-butyl phenylcarbamate 
• 108-86-1 bromobenzene 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 870703-82-5 tert-butyl (2'-formyl-[1,1'-biphenyl]-4-yl)carbamate 
• 197435-52-2 [4-(pyridin-4-yl)phenyl]carbamic acid tert-butyl ester 
• 147696-69-3 (4-Amino-phenyl)-pyridin-3-yl-methanone 
• 6278-73-5 2-(4-aminophenyl)benzothiazole 
• 43036-17-5 2-(4-aminophenyl)-6-methoxybenzothiazole 
• 937737-95-6 thioacetic acid S-(4-tert-butoxycarbonylaminophenyl) ester 
• 312760-48-8 3-{[5-(4-amino-phenyl)-thiophene-2-carbonyl]-amino}-2-benzenesulfonylamino-propionic acid tert-butyl ester 
• 312760-49-9 C₃₅H₄₅N₅O₉S₂ 

Relevant academic research and scientific papers

A mild and green method for the N-BOC protection of amines without assistant of catalyst under solvent-free conditions

A facile, green and versatile method for the Boc protection of amines has been developed by a treatment with (Boc)2O without any additive at room temperature. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines. The advantages of this method are green, simplicity, short reaction times and excellent yields.

Identification of pyrazine-based TrkA inhibitors: Design, synthesis, evaluation, and computational modeling studies

Trk receptors play a key role in the development and maintenance of neuronal networks. Recent evidence suggests that the Trk family, specifically TrkA, is an important driver for tumour growth, inflammatory and neuropathic pain, and chemoresistance. Through a computational screen, a novel Trk active pharmacophore was identified and a series of pyrazine-based inhibitors were developed, which potently inhibited TrkA. Inhibitors displayed the highest activity on TrkA when screened against a small, tyrosine kinase panel and also exhibited a non-linear SAR. Predicted binding modes of the inhibitors were examined, which identified exploitable regions for future development of more advanced inhibitors. This journal is

Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly

Macrocycles based on directional bonding and dynamic covalent bond exchange can be designed with specific pore shapes, sizes, and functionality. These systems retain many of the design criteria and desirable aspects of two-dimensional (2D) covalent organi

Heterobimetallic dinuclear lanthanide alkoxide complexes as acid-base bifunctional catalysts for synthesis of carbamates under solvent-free conditions

Heterobimetallic dinuclear lanthanide alkoxide complexes Ln2Na8(OCH2CH2NMe2)12(OH)2 [Ln: I (Nd), II (Sm), III (Yb) and IV (Y)] were used as efficient acid-base bifunctional catalysts for the synthesis of carbamates from dialkyl carbonates and amines as well as the N-Boc protection of amines. The cooperative catalysts showed high catalytic activity and a wide scope of substrates with good to excellent yields under solvent-free conditions. The systems have shown higher catalytic activities due to the noteworthy synergistic interactions of Lewis acid center-Br?nsted basic center. The comparison of catalytic efficiency between mono- and dinuclear heterobimetallic lanthanide alkoxide analogues was also investigated.

The synthesis of a rigid conjugated viologen and its cucurbituril pseudorotaxanes

A linear viologen (bis[4-(4-pyridinyl)phenyl] viologen, BPPV) characterized by a fully-conjugated structure was synthesized through Zinke reaction. BPPV consists of a unique linear sexiaryl structure and is apt to be encapsulated by cucurbit[n]uril (CB[n]

Microwave assisted mild, rapid, solvent-less, and catalyst-free chemoselective N-tert-butyloxycarbonylation of amines

Microwave assisted simple, rapid, solventless, and catalyst-free chemoselective method for the protection of amino group in aromatic, aliphatic, heterocyclic, aralkyl amines, phenyl hydrazine, and amino acid esters in good to excellent isolated yield (83-98%) in short reaction time (2-12 min) has been reported.

Efficient N-Boc protection of amines by a reusable heterogeneous solid acid nanocatalyst at room temperature

An efficient and rapid protocol for chemoselective N-Boc protection of various structurally different aryl, aliphatic, and heterocyclic amines is reported with (Boc)2O using mesoporous silica phenylsulfonic acid (SBA-15-Ph-SO3H) as a recyclable and heterogeneous solid acid nanocatalyst under solvent-free condition at ambient temperature. The catalyst can be easily recovered and reused for ten reaction cycles for protection of amines without considerable loss of activity. The advantages of this green method are simplicity, easy workup, chemoselectivity, short reaction time, and excellent yield.

Integrating Hydrogen Production and Transfer Hydrogenation with Selenite Promoted Electrooxidation of α-Nitrotoluenes to E-Nitroethenes

Developing an electrochemical carbon-added reaction with accelerated kinetics to replace the low-value and sluggish oxygen evolution reaction (OER) is markedly significant to pure hydrogen production. Regulating the critical steps to precisely design electrode materials to selectively synthesize targeted compounds is highly desirable. Here, inspired by the surfaced adsorbed SeOx2? promoting OER, NiSe is demonstrated to be an efficient anode enabling α-nitrotoluene electrooxidation to E-nitroethene with up to 99 % E selectivity, 89 % Faradaic efficiency, and the reaction rate of 0.25 mmol cm?2 h?1 via inhibiting side reactions for energy-saving hydrogen generation. The high performance can be associated with its in situ formed NiOOH surface layer and absorbed SeOx2? via Se leaching-oxidation during electrooxidation, and the preferential adsorption of two -NO2 groups of intermediate on NiOOH. A self-coupling of α-carbon radicals and subsequent elimination of a nitrite molecule pathway is proposed. Wide substrate scope, scale-up synthesis of E-nitroethene, and paired productions of E-nitroethene and hydrogen or N-protected aminoarenes over a bifunctional NiSe electrode highlight the promising potential. Gold also displays a similar promoting effect for α-nitrotoluene transformation like SeOx2?, rationalizing the strategy of designing materials to suppress side reactions.

A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.

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.