60144-53-8

Basic information

• Product Name: 4-FLUOROANILINE, N-BOC PROTECTED
• Synonyms: 4-FLUOROANILINE, N-BOC PROTECTED;TERT-BUTYL 4-FLUOROPHENYLCARBAMATE;tert-Butyl (4-fluorophenyl)carbamate, N-(tert-Butoxycarbonyl)-4-fluoroaniline;4-Fluoroaniline,N-BOCprotected97%;1-((4-fluorophenyl)carbamoyl)cyclopropane-1-carboxylicacid
• CAS NO: 60144-53-8
• Molecular Formula: C₁₁H₁₄FNO₂
• Molecular Weight: 211.23
• Mol File: 60144-53-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 4-FLUOROANILINE, N-BOC PROTECTED(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUOROANILINE, N-BOC PROTECTED(60144-53-8)
• EPA Substance Registry System: 4-FLUOROANILINE, N-BOC PROTECTED(60144-53-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 60144-53-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluoroaniline, N-BOC protected, is used as a key intermediate in the synthesis of various pharmaceuticals. The BOC protecting group allows for selective reactions to occur at other sites on the molecule, facilitating the creation of complex drug structures. Once the desired transformations are complete, the BOC group can be removed under mild conditions to reveal the reactive aniline group for further reactions or final product formation.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Fluoroaniline, N-BOC protected, serves as an intermediate for the development of new pesticides and other agrochemicals. The fluorine atom in the molecule can enhance the lipophilicity and metabolic stability of the final product, which is crucial for the effectiveness and safety of agrochemicals.
Used in Organic Synthesis:
4-Fluoroaniline, N-BOC protected, is utilized in the synthesis of a wide range of organic compounds. The BOC group provides a means to control the reactivity of the aniline group, allowing chemists to carry out reactions at other sites on the molecule selectively. This selective reactivity is particularly valuable in the synthesis of complex organic molecules where multiple functional groups are present.
Used in Fluorine Chemistry:
The presence of the fluorine atom in 4-Fluoroaniline, N-BOC protected, makes it a valuable compound in fluorine chemistry. Fluorine is known for its unique properties, such as high electronegativity and small size, which can significantly influence the physical and chemical properties of organic molecules. 4-FLUOROANILINE, N-BOC PROTECTED can be used to explore the effects of fluorination on molecular behavior and reactivity in various chemical processes.

Upstream product

• 460-00-4 1-Bromo-4-fluorobenzene 
• 371-40-4 4-fluoroaniline 
• 34619-03-9 tert-butyldicarbonate 
• 58377-40-5 tert-butyl N-hydroxy-N-phenylcarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 350-46-9 4-Fluoronitrobenzene 
• 4248-19-5 tert-butyl carbazate 
• 540-36-3 para-difluorobenzene 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 110969-43-2 tert-butyl 4-tert-butylphenylcarbamate 
• 3422-01-3 tert-butyl phenylcarbamate 
• 1239374-03-8 tert-butyl 4-fluorophenyl(3-perfluorooctylpropoxy)carbamate 

Downstream Products

• 396-30-5 6-fluoroquinoline 
• 137595-45-0 3-Phenyl-6-fluoroquinoline 
• 137595-46-1 3-Methyl-6-fluoroquinoline 
• 329216-94-6 N-(tert-butoxycarbonyl)-4-fluoro-2-thiophenylaniline 
• 923947-57-3 (4-bromo-thiazol-2-yl)-(4-fluoro-phenyl)-carbamic acid tert-butyl ester 
• 1033619-78-1 (6-bromo-pyridin-2-ylmethyl)-(4-fluoro-phenyl)-carbamic acid tert-butyl ester 
• 1033619-90-7 2-chloro-thiazol-4-ylmethyl-4-fluorophenylcarbamic acid tert-butyl ester 
• 1033619-85-0 (4-fluoro-phenyl)-(3-iodo-benzyl)-carbamic acid tert-butyl ester 
• 1033619-92-9 (4-fluoro-phenyl)-(2-piperidin-1-yl-thiazol-4-ylmethyl)-carbamic acid tert-butyl ester 
• 1033619-94-1 (2-chloro-thiazol-5-ylmethyl)-(4-fluorophenyl)-carbamic acid tert-butyl ester 
• 1033619-82-7 (4-fluoro-phenyl)-(4-iodo-benzyl)-carbamic acid tert-butyl ester 
• 371-40-4 4-fluoroaniline 
• 330793-01-6 (4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester 
• 3422-01-3 tert-butyl phenylcarbamate 

Relevant articles and documents

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.

Identification and Profiling of a Novel Diazaspiro[3.4]octane Chemical Series Active against Multiple Stages of the Human Malaria Parasite Plasmodium falciparum and Optimization Efforts

A novel diazaspiro[3.4]octane series was identified from a Plasmodium falciparum whole-cell high-throughput screening campaign. Hits displayed activity against multiple stages of the parasite lifecycle, which together with a novel sp3-rich scaffold provided an attractive starting point for a hit-to-lead medicinal chemistry optimization and biological profiling program. Structure-activity-relationship studies led to the identification of compounds that showed low nanomolar asexual blood-stage activity (50 nM) together with strong gametocyte sterilizing properties that translated to transmission-blocking activity in the standard membrane feeding assay. Mechanistic studies through resistance selection with one of the analogues followed by whole-genome sequencing implicated the P. falciparum cyclic amine resistance locus in the mode of resistance.

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.

4 - Fluorine substituted aryl amine compound and synthesis method thereof

The invention discloses a synthesis method of 4 -fluorine substituted aryl amine compound, which comprises the following steps: 1) taking acyl-protected phenylhydroxylamine as a substrate, and generating 4 -fluorine substituted aniline compound under basic conditions by taking sulfonyl fluoride as a fluorine source in a polar solvent. 2) The deprotection is carried out under dilute acid conditions or Pd by catalytic hydrogenation to give the 4 - fluorine-substituted aryl amine compound. 4 - Fluorine substituted aniline compounds which are synthesized by the invention greatly increase the lipophilic property due to the introduction of fluorine atoms, and can be widely applied to preparation of fluorine-containing drugs and pesticide and dye intermediates. , The adopted raw materials are industrial products, are cheap and easily available, and are commercially available. 4 - Fluoroaryl aniline prepared by the method is high in yield, and the product with the purity 90% can be obtained in a yield of more than ≥ 99%. The method is simple to operate and low in cost, is very suitable for industrialization, and can be widely popularized and used.

Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst

An efficient approach for the Chemoselective N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation of side products like urea, oxazolidinone, isocyanate, and N, N-di-Boc derivatives makes the present protocol desirable.

ACETAMIDO DERIVATIVES AS DNA POLYMERASE THETA INHIBITORS

Disclosed herein are certain acetamido derivatives that are DNA Polymerase Theta (Polθ) inhibitors of Formula (I). Also, disclosed are pharmaceutical compositions comprising such compounds and methods of treating diseases treatable by inhibition of Polθ such as cancer, including homologous recombination (HR) deficient cancers.

Electrophotocatalytic SNAr Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base

The electrophotocatalytic SNAr reaction of unactivated aryl fluorides at ambient temperature without strong base is demonstrated.

Harnessing Cascade Suzuki-Cyclization Reactions of Pyrazolo[3,4-b]pyridine for the Synthesis of Tetracyclic Fused Heteroaromatics

Numerous procedures have been described for the functionalization of pyrazolo[3,4-b]pyridine, mainly involving nucleophilic substitutions at the C-4 position or esterifications/amidations at the C-5 position. In this paper, we describe a robust, easy to implement protocol for the Suzuki cross-coupling reaction of chloroarene 2, followed by in-situ lactonization to provide chromenopyrazolopyridines. The extension of the scope of the reaction to fused naphthyridinones is also reported. This strategy gave access to 10 original pyrazolopyridine-containing tetracyclic compounds.

[TPA][Pro] ionic liquid as efficient reaction medium for N-tert-Boc protection of amines

A facile and efficient N-tert-Boc protection of amines is described by the reaction of various primary, secondary, benzylic and aryl amines with di-tert-butyl dicarbonate in the ionic liquid [TPA][Pro] at room temperature. All the N-tert-butylcarbamates are afforded in excellent yields. A catalyst-free method was developed and the ionic liquid [TPA][Pro] can be recovered and reused for several times without loss of its activity.

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.