22208-39-5

Basic information

• Product Name: 2-cyano-N-(4-nitrophenyl)acetamide
• Synonyms: 2-cyano-N-(4-nitrophenyl)acetamide;2-cyano-N-(4-nitrophenyl)ethanamide
• CAS NO: 22208-39-5
• Molecular Formula: C₉H₇N₃O₃
• Molecular Weight: 205.17018
• Mol File: 22208-39-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 501.8 °C at 760 mmHg
• Flash Point: 257.3 °C
• Appearance: /
• Density: 1.422 g/cm³
• CAS DataBase Reference: 2-cyano-N-(4-nitrophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-N-(4-nitrophenyl)acetamide(22208-39-5)
• EPA Substance Registry System: 2-cyano-N-(4-nitrophenyl)acetamide(22208-39-5)

Safety Data

• Hazardous Substances Data: 22208-39-5(Hazardous Substances Data)

Usage

Description

2-cyano-N-(4-nitrophenyl)acetamide, also known as 4-Nitrophenylacetonitrile, is a chemical compound that belongs to the class of amides and nitriles. It has the molecular formula C10H7N3O3 and is characterized by its pale yellow solid appearance at room temperature. 2-cyano-N-(4-nitrophenyl)acetamide is primarily used as an intermediate in the synthesis of pharmaceuticals and other organic compounds due to its distinctive nitro and cyanide functional groups, which contribute to its reactivity and chemical properties. It is important to handle and store 2-cyano-N-(4-nitrophenyl)acetamide with appropriate safety measures, as it can be flammable under certain conditions.

Uses

Used in Pharmaceutical Industry:
2-cyano-N-(4-nitrophenyl)acetamide is used as a chemical intermediate for the synthesis of various pharmaceuticals and organic compounds. Its unique functional groups, including the nitro and cyanide groups, make it a valuable component in the development of new drugs and medicinal agents.
Used in Organic Synthesis:
In the field of organic synthesis, 2-cyano-N-(4-nitrophenyl)acetamide serves as a key intermediate for the preparation of a wide range of organic compounds. Its reactivity and chemical properties allow it to be used in various chemical reactions, contributing to the synthesis of diverse organic molecules with potential applications in various industries.

Upstream product

• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 372-09-8 cyanoacetic acid 
• 100-01-6 4-nitro-aniline 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 

Downstream Products

• 4452-08-8 cyanoketene 
• 100-01-6 4-nitro-aniline 
• 136186-26-0 (Z)-2-Cyano-3-hydroxy-N-(4-nitro-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide 

Relevant articles and documents

Identification of Novel Fused Heteroaromatics-Based MALT1 Inhibitors by High-Throughput Screening to Treat B Cell Lymphoma

Development of mucosa-associated lymphoid tissue lymphoma translocation protein 1 (MALT1) inhibitors is of great value and significance in the treatment of neoplastic disorders and inflammatory and autoimmune diseases. However, there is a lack of effective MALT1 inhibitors in clinic. Herein, a novel class of potent 5-oxo-1-thioxo-4,5-dihydro-1H-thiazolo[3,4-a]quinazoline-based MALT1 inhibitors and their covalent derivatives were first identified and designed through high-throughput screening. We demonstrated that compounds 15c, 15e, and 20c effectively inhibited the MALT1 protease and displayed selective cytotoxicity to activated B cell-like diffuse large B cell lymphoma with low single-digit micromolar potency. Furthermore, compound 20c specifically repressed NF-κB signaling and induced cell apoptosis in MALT1-dependent TMD8 cells in a dose-dependent manner. More importantly, 20c showed good pharmacokinetic properties and antitumor efficacy with no significant toxicity in the TMD8 xenograft tumor model. Collectively, this study provides valuable lead compounds of MALT1 inhibitors for further structural optimization and antitumor mechanism study.

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).

2-Imino 2H-chromene and 2-(phenylimino) 2H-chromene 3-aryl carboxamide derivatives as novel cytotoxic agents: synthesis, biological assay, and molecular docking study

The inhibition of AKR1B10 has been recognized as a potential therapeutic approach to the treatment of various types of cancers. A novel series of compounds with imino-2H-chromen and phenylimino-2H-chromen scaffolds were synthesized by Knoevenagel condensation reaction. The in vitro cytotoxic activity of synthesized compounds was evaluated against MOLT-4 and SK-OV-3 cells. Among the tested compounds, N-(3,4-dimethoxyphenyl)-2-(phenylimino)-2H-chromene-3-carboxamide (8g) demonstrated potent inhibitory activity against both examined cell lines. The results of the molecular docking study suggested that this compound is involved in critical hydrogen-bonding interactions with the Val301 and Lue302 of AKR1B10 catalytic site.