399-35-9

Usage

Chemical Properties

GREY NEEDLE-LIKE CRYSTALLINE POWDER

Upstream product

• 2106-02-7 2-chloro-4-fluoroaniline 
• 108-24-7 acetic anhydride 
• 351-83-7 4'-fluoroacetanilide 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 161950-66-9 2-chloro-4-fluorophenylammonium chloride 
• 57265-05-1 1-[p-chloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(p-fluorophenyl)carbamoyl-methyl]imidazolium chloride 
• 153505-32-9 2-chloro-4-fluoro-6-nitro-benzenamine 
• 153505-33-0 3-chloro-5-fluoro-1,2-phenylenediamine 

Relevant academic research and scientific papers

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2-Dichloroethane

Although the application of 1,2-dichloroethane (DCE) as a chlorinating reagent in organic synthesis with the concomitant release of vinyl chloride as a useful byproduct is a fantastic idea, it still presents a tremendous challenge and has not yet been achieved because of the harsh dehydrochlorination conditions and the sluggish C?H chlorination process. Here we report a bifunctional electrocatalysis strategy for the catalytic dehydrochlorination of DCE at the cathode simultaneously with anodic oxidative aromatic chlorination using the released HCl as the chloride source for the efficient synthesis of value-added (hetero)aryl chlorides. The mildness and practicality of the protocol was further demonstrated by the efficient late-stage chlorination of bioactive molecules.

A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst

A simple and practical heterogeneous Cu-MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu-MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N-halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.

A Four-Step Synthesis of (±)-γ-Lycorane via Pd0-Catalyzed Double C(sp2)-H/C(sp3)-H Arylation

An expedient synthesis of lycorine alkaloids is reported using a palladium(0)-catalyzed double C-X/C-H arylation as the key step. The selectivity of this reaction was controlled through the judicious choice of the two halogen atoms, and its generality was

2-aminopyrimidine compounds and application thereof

The invention relates to 2-aminopyrimidine compounds with structures as shown in a formula I which is described in the specification, and pharmaceutically acceptable salts, stereoisomers or prodrug molecules thereof, belonging to the technical field of chemical medicines. The compounds are capable of realizing high-selectivity inhibition of the activity of the FGFR4 protein kinase without inhibition of the activities of other member kinases (i.e., FGFR1, FGFR2 and FGFR3) in the FGFRs family. The compounds can effectively inhibit the growth of tumor cells caused by the abnormity of a FGFR4 signaling pathway, and is applicable to prevention and treatment of transitional proliferative diseases such as tumors in human beings and other mammals caused by the abnormity of the FGFR4 signaling pathway.

Regioselective nitration of anilines with Fe(NO3)3·9H2O as a promoter and a nitro source

An efficient Fe(NO3)3·9H2O promoted ortho-nitration reaction of aniline derivatives has been developed. This reaction may go through a nitrogen dioxide radical (NO2) intermediate, which is generated by the thermal decomposition of iron(iii) nitrate. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the broad substrate scope and applications.

Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis

Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.

2-Aminopyrimidine Derivatives as New Selective Fibroblast Growth Factor Receptor 4 (FGFR4) Inhibitors

A series of 2-aminopyrimidine derivatives were designed and synthesized as highly selective FGFR4 inhibitors. One of the most promising compounds 2n tightly bound FGFR4 with a Kd value of 3.3 nM and potently inhibited its enzymatic activity with an IC50 value of 2.6 nM, but completely spared FGFR1/2/3. The compound selectively suppressed proliferation of breast cancer cells harboring dysregulated FGFR4 signaling with an IC50 value of 0.38 μM. Furthermore, 2n exhibited extraordinary target specificity in a Kinome-wide screen against 468 kinases, with S(35) and S(10) selectivity scores of 0.01 and 0.007 at 1.0 μM, respectively.