13519-80-7

Usage

Uses

Used in Dye Production:
4-Chloro-N-allylaniline is utilized as a key intermediate in the synthesis of various dyes. Its unique chemical structure allows for the creation of a wide range of colorants used in different industries.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 4-Chloro-N-allylaniline serves as an important intermediate for the development and production of various medications. Its chemical properties make it a valuable component in the synthesis of drugs with specific therapeutic applications.
Used in Agrochemical Production:
4-Chloro-N-allylaniline is also employed as an intermediate in the manufacturing of agrochemicals. Its role in this industry is crucial for the development of products designed to enhance crop protection and improve agricultural yields.
It is important to handle 4-Chloro-N-allylaniline with care due to its hazardous nature, ensuring proper safety measures are in place to minimize potential health risks to individuals and the environment.

InChI:InChI=1/C9H10ClN/c1-2-7-11-9-5-3-8(10)4-6-9/h2-6,11H,1,7H2

Upstream product

• 15022-08-9 diallylcarbonate 
• 106-47-8 4-chloro-aniline 
• 106-95-6 allyl bromide 
• 1121-60-4 pyridine-2-carbaldehyde 
• 107-18-6 allyl alcohol 
• 589-09-3 N-allyl-N-phenylamine 
• 22774-67-0 4-chloro-N-prop-2-ynylaniline 
• 1172142-55-0 N-allyl-N-(4-chlorophenyl)-2-nitrobenzenesulfonamide 
• 18437-66-6 N-(t-butoxycarbonyl)-4-chloroaniline 
• 3296-05-7 1-azido-4-chlorobenzene 
• 71-43-2 benzene 
• 2622-05-1 allylmagnesium bromide 
• 100-00-5 4-chlorobenzonitrile 
• 119803-83-7 allyl pheny telluroxide 

Downstream Products

• 882787-24-8 N-(2-allyl-4-chloro-phenyl)-acrylamide 
• 1172142-67-4 methyl 2-[N-allyl-N-(4-chlorophenyl)sulfamoyl]acetate 
• 1202021-53-1 C₁₈H₂₃BrClN 
• 1202021-56-4 C₂₀H₁₉BrClN 
• 1202021-47-3 C₁₅H₁₇BrClN 
• 1202021-49-5 C₁₆H₁₉BrClN 
• 1202021-54-2 C₂₀H₁₉BrClN 
• 1202021-51-9 C₁₇H₂₁BrClN 
• 1447138-12-6 N-benzyloxycarbonyl-(E)-4-(2-amino-5-chlorophenyl)-1-phenylbut-2-en-1-one 
• 1447138-20-6 1-phenyl-2-(N-benzyloxycarbony-5-chlorolindolin-2-yl)ethanone 
• 1447138-36-4 benzyl (2-allyl-4-chlorophenyl)carbamate 
• 66236-14-4 N-(2-allyl-4-chlorophenyl)methanesulfonamide 
• 340011-50-9 N-allyl N-(4-chlorophenyl)acrylamide 
• 1374693-97-6 C₂₅H₂₄ClNO₆S 

Relevant academic research and scientific papers

One-pot Construction of Difluorinated Pyrrolizidine and Indolizidine Scaffolds via Copper-Catalyzed Radical Cascade Annulation

A convenient approach to the synthesis of diverse difluorinated nitrogen-containing polycycles via a copper-catalyzed radical cascade annulation of amine-containing olefins and ethyl bromodifluoroacetate was developed. Three new bonds, including a Csp3 ?CF2 and two C?N bonds, are forged simultaneously in this strategy. Through this strategy, a series of difluorinated pyrrolizidine and indolizidine derivatives have been conveniently synthesized in good yields. (Figure presented.).

Platinum(II)-Crosslinked Single-Chain Nanoparticles: An Approach towards Recyclable Homogeneous Catalysts

We introduce the synthesis and in-depth characterization of platinum(II)-crosslinked single-chain nanoparticles (PtII-SCNPs) to demonstrate their application as a recyclable homogeneous catalyst. Specifically, a linear precursor copolymer of styrene and 4-(diphenylphosphino)styrene was synthesized via nitroxide-mediated polymerization. The triarylphosphine ligand moieties along the backbone allowed for the intramolecular crosslinking of single chains via the addition of [Pt(1,5-cyclooctadiene)Cl2] in dilute solution. The successful formation of well-defined PtII-SCNPs was evidenced by size exclusion chromatography, dynamic light scattering, nuclear magnetic resonance (1H, 31P{1H}, 195Pt), and diffusion-ordered spectroscopy. Finally, the activity of the PtII-SCNPs as homogeneous, yet recyclable catalyst was successfully demonstrated using the example of the amination of allyl alcohol.

Rate acceleration and diastereoselectivity in chelation-controlled indium-promoted Barbier allylation of pyridine-2- and quinoline-2-imines in aqueous solvents

The imines generated in situ from 2-pyridinecarboxaldehyde/2- quinolinecarboxaldehyde and aryl amines undergo indium-mediated Barbier allylation in aqueous media to provide homoallylic amines. Crotyl and cinnamyl bromides lead to diastereoselective allyla

Thioamination of Alkenes with Hypervalent Iodine Reagents

An efficient thioamination of alkenes mediated by iodine(III) reagents is described. The use of different sulfur nucleophiles allows the flexible synthesis of 1,2-aminothiols from alkenes. By employing chiral iodine(III) reagents, a stereoselective version of the thioamination protocol has also been developed.

Indium-mediated barbier reactions of azides: A facile synthesis of N-allylamine derivatives

N-Allylic amines are conveniently prepared in high yields by the reaction of azides with allylindium reagents in the presence of sodium iodide in DMF at ambient temperature.

Nickel-Catalyzed Aminofluoroalkylation of Alkenes: Access to Difluoroalkylated N-Containing Heterocyclic Compounds

A nickel-catalyzed aminofluoroalkylative cyclization of unactive alkenes with iododifluoromethyl ketones was developed to construct versatile difluoroalkylated Nitrogen-containing heterocycles including aziridines, pyrrolidines and piperidines in moderate to high yields. This method features a broad substrate scope and has been demonstrated on gram scale.

Copper-Catalyzed Allylation of Amines with Cyclopropyldiphenylsulfonium Trifluoromethanesulfonate

Cyclopropyldiphenylsulfonium salt, a famous ylide precursor previously extensively employed in the preparation of cyclic compounds, has been successfully utilized as an efficient allylation reagent in this work. The copper-catalyzed reactions of cyclopropyldiphenylsulfonium trifluoromethanesulfonate with amines in the presence of an appropriate ligand provided the N-allylated products in good yields. Aliphatic/ aromatic amines and primary/secondary amines were all converted under mild reaction conditions. This protocol was also applicable to N-functionalization of drug molecules, supplying the corresponding N-allylated compounds in satisfactory yields. The reaction, which showed good functional group tolerance with a wide range of substrates and excellent chemoselectivity, offers an interesting method for the synthesis of N-allyl amines.

Fused ring compound and preparation method thereof

The invention provides a fused ring compound and a preparation method thereof. In the method, precursor compounds A and B prepared under the conditions of triethylamine as a base, DMF as a solvent andpalladium acetate and triphenylphosphine as a catalyst react to generate a series of new fused ring compounds with a unique stereoselectivity. Compared with the conventional fused ring compound, thefused ring compound prepared by the invention has a more complicated structure, a mild reaction condition and a high reaction yield. The fused ring compound also shows a broader prospect of use in chemical production and clinical medicine.

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor

We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.