24522-30-3

Basic information

• Product Name: 2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide
• Synonyms: 2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide;AcetaMide, 2-cyano-N-[4-(trifluoroMethyl)phenyl]-;Leflunomide Impurity H;Leflunomide EP Impurity H;2-Cyano-N-[4-(trifluoromethyl)phenyl]acetamide
• CAS NO: 24522-30-3
• Molecular Formula: C₁₀H₇F₃N₂O
• Molecular Weight: 228.18
• Mol File: 24522-30-3.mol

Chemical Properties

• Melting Point: 145-147℃
• Boiling Point: 386.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.375±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.63±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide(24522-30-3)
• EPA Substance Registry System: 2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide(24522-30-3)

Safety Data

• Hazardous Substances Data: 24522-30-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide is used as a synthetic intermediate for the preparation of aminothiophene carboxylates and carboxamides. These compounds serve as adenosine A1 receptor allosteric enhancers, which have potential applications in the treatment of various diseases and conditions, such as neurodegenerative disorders, cognitive impairment, and certain types of cancer.
Additionally, 2-cyano-N-[4-(trifluoromethyl)phenyl]acetamide is utilized in the synthesis of (1,2,3-triazol-4-yl)benzenamines. These compounds are known to be inhibitors against vascular endothelial growth factor (VEGF) receptors 1 and 2. Inhibiting these receptors can be beneficial in the treatment of various diseases, particularly those related to angiogenesis, such as cancer, age-related macular degeneration, and diabetic retinopathy.

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 
• 621-03-4 cyanoacetanilide 
• 2926-29-6 Langlois reagent 
• 105-56-6 ethyl 2-cyanoacetate 
• 16130-58-8 cyanoacetic acid chloride 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 136186-08-8 (Z)-2-Cyano-3-hydroxy-3-(4-trifluoromethoxy-phenyl)-N-(4-trifluoromethyl-phenyl)-acrylamide 
• 136186-13-5 (Z)-3-[4-(4-Chloro-phenoxy)-phenyl]-2-cyano-3-hydroxy-N-(4-trifluoromethyl-phenyl)-acrylamide 
• 136186-01-1 (Z)-2-Cyano-3-(4-fluoro-phenyl)-3-hydroxy-N-(4-trifluoromethyl-phenyl)-acrylamide 
• 183945-57-5 2-cyano-3-cyclopentyl-3-hydroxy-N-(4-(trifluoromethyl)phenyl)acrylamide 
• 183945-55-3 2-cyano-3-cyclopropyl-3-hydroxy-N-(4-(trifluoromethyl)phenyl)acrylamide 
• 136185-97-2 2-cyano-3-hydroxy-3-phenyl-N-(4-(trifluoromethyl)phenyl)acrylamide 
• 171197-18-5 2-cyano-3-hydroxy-4-methyl-N-(4-(trifluoromethyl)phenyl)pent-2-enamide 
• 183945-56-4 2-cyano-3-cyclobutyl-3-hydroxy-N-(4-(trifluoromethyl)phenyl)acrylamide 
• 163451-81-8 teriflunomide 
• 1248706-19-5 C₂₁H₁₉F₃N₂O₃ 
• 136186-09-9 (Z)-2-Cyano-3-hydroxy-3-(4-nitro-phenyl)-N-(4-trifluoromethyl-phenyl)-acrylamide 
• 136186-02-2 (Z)-3-(4-Chloro-phenyl)-2-cyano-3-hydroxy-N-(4-trifluoromethyl-phenyl)-acrylamide 
• 136186-11-3 (Z)-2-Cyano-3-hydroxy-3-p-tolyl-N-(4-trifluoromethyl-phenyl)-acrylamide 
• 136185-97-2 (Z)-2-Cyano-3-hydroxy-3-phenyl-N-(4-trifluoromethyl-phenyl)-acrylamide 

Relevant articles and documents

NEW MALONITRILE DERIVATIVES

The invention relates to a compound of formula (I) wherein R1-R2 are as defined in the description and in the claims. The compound of formula (I) can be used as a medicament.

Optimization of 2-acylaminocycloalkylthiophene derivatives for activity against Staphylococcus aureus RnpA

Staphylococcus aureus is well-recognized to cause debilitating bacterial infections that are difficult to treat due to the emergence of antibiotic resistance. As such, there is a need to develop new antimicrobials for the therapeutic intervention of S. au

Preparation process of continuous-flow teriflunomide

To the preparation process, cyanoacetic acid is used as a starting material, cyanoacetyl chloride is prepared by chlorination, and a tertamine intermediate is synthesized by cyanacetyl chloride and p-trifluoromethylaniline, and an intermediate is synthesized with acetyl chloride. The invention has high safety. The utility model has the advantages of low cost, low energy consumption and high production yield.

Preparation method of aniline para-trifluoromethylated derivative

The invention discloses a preparation method of an aniline para-trifluoromethylated derivative. The method comprises the following steps: sequentially adding an aniline derivative, 4, 5-dichlorofluorescein, potassium persulfate and sodium trifluoromethanesulfinate into a glass reaction tube, and reacting at room temperature (23-25 DEG C) under 40W blue LED (light-emitting diode) by taking dimethyl sulfoxide as a solvent to obtain the aniline para-trifluoromethylated derivative. According to the invention, the aniline derivative is used as an initiator, and the raw materials are easily available and various; products obtained by the method disclosed by the invention have various types and can be directly applied to modification of drug molecules; and meanwhile, the synthesis route is safe and easy to implement, the cost is low, the reaction operation and post-treatment process are simple, the selectivity is good, the side reaction is few, and the amplification reaction can be carried out.

Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones

The first nickel-catalyzed oxidative domino Csp3-H/N-H double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3-H bond, representing an effective way to construct heterocycles.

Preparation method of teriflunomide

The invention relates to the technical field of medicinal chemistry, in particular to a preparation method of teriflunomide. The preparation method includes: (1) mixing cyanoacetic acid, a condensingagent, an aprotic solvent and an alkaline reagent, and c

Agonist-mediated switching of ion selectivity in TPC2 differentially promotes lysosomal function

Ion selectivity is a defining feature of a given ion channel and is considered immutable. Here we show that ion selectivity of the lysosomal ion channel TPC2, which is hotly debated (Calcraft et al., 2009; Guo et al., 2017; Jha et al., 2014; Ruas et al., 2015; Wang et al., 2012), depends on the activating ligand. A high-throughput screen identified two structurally distinct TPC2 agonists. One of these evoked robust Ca2+-signals and non-selective cation currents, the other weaker Ca2+-signals and Na+-selective currents. These properties were mirrored by the Ca2+- mobilizing messenger, NAADP and the phosphoinositide, PI(3,5)P2, respectively. Agonist action was differentially inhibited by mutation of a single TPC2 residue and coupled to opposing changes in lysosomal pH and exocytosis. Our findings resolve conflicting reports on the permeability and gating properties of TPC2 and they establish a new paradigm whereby a single ion channel mediates distinct, functionally-relevant ionic signatures on demand.

Development of Novel AKR1C3 Inhibitors as New Potential Treatment for Castration-Resistant Prostate Cancer

Aldo-keto reductase (AKR) 1C3 catalyzes the synthesis of active androgens that promote the progression of prostate cancer. AKR1C3 also contributes to androgen-independent cell proliferation and survival through the metabolism of prostaglandins and reactive aldehydes. Because of its elevation in castration-resistant prostate cancer (CRPC) tissues, AKR1C3 is a promising therapeutic target for CRPC. In this study, we found a novel potent AKR1C3 inhibitor, N-(4-fluorophenyl)-8-hydroxy-2-imino-2H-chromene-3-carboxamide (2d), and synthesized its derivatives with IC50 values of 25-56 nM and >220-fold selectivity over other AKRs (1C1, 1C2, and 1C4). The structural factors for the inhibitory potency were elucidated by crystallographic study of AKR1C3 complexes with 2j and 2l. The inhibitors suppressed proliferation of prostate cancer 22Rv1 and PC3 cells through both androgen-dependent and androgen-independent mechanisms. Additionally, 2j and 2l prevented prostate tumor growth in a xenograft mouse model. Furthermore, the inhibitors significantly augmented apoptotic cell death induced by anti-CRPC drugs (abiraterone or enzalutamide).

Synthesis, cytotoxic characterization, and SAR study of imidazo[1,2-b]pyrazole-7-carboxamides

The synthesis and in vitro cytotoxic characteristics of new imidazo[1,2-b]pyrazole-7-carboxamides were investigated. Following a hit-to-lead optimization exploiting 2D and 3D cultures of MCF-7 human breast, 4T1 mammary gland, and HL-60 human promyelocytic leukemia cancer cell lines, a 67-membered library was constructed and the structure–activity relationship (SAR) was determined. Seven synthesized analogues exhibited sub-micromolar activities, from which compound 63 exerted the most significant potency with a remarkable HL-60 sensitivity (IC50 = 0.183 μM).

AN IMPROVED PROCESS FOR THE PREPARATION OF TERIFLUNOMIDE

The present invention relates to an improved process for the preparation of Teriflunomide with high yield and high purity. The present invention also relates to a process for the preparation of teriflunomide which is free from genotoxic impurities.