349-02-0

Basic information

• Product Name: 4-FLUORO-3-NITROBENZAMIDE
• Synonyms: 4-FLUORO-3-NITROBENZAMIDE
• CAS NO: 349-02-0
• Molecular Formula: C₇H₅FN₂O₃
• Molecular Weight: 184.13
• Mol File: 349-02-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 153 °C
• Boiling Point: 293.313°C at 760 mmHg
• Flash Point: 131.192°C
• Appearance: /
• Density: 1.483g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.79±0.50(Predicted)
• CAS DataBase Reference: 4-FLUORO-3-NITROBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUORO-3-NITROBENZAMIDE(349-02-0)
• EPA Substance Registry System: 4-FLUORO-3-NITROBENZAMIDE(349-02-0)

Safety Data

• Hazardous Substances Data: 349-02-0(Hazardous Substances Data)

Usage

General Description

4-Fluoro-3-nitrobenzamide is a chemical compound with the molecular formula C7H5FN2O3. It is a yellow crystalline solid and is commonly used in the pharmaceutical and research industries as a building block for the synthesis of various organic compounds. This chemical is a derivative of benzamide, which has a benzene ring with an amide functional group, and it is characterized by the presence of a fluorine atom at the 4-position and a nitro group at the 3-position on the benzene ring. 4-Fluoro-3-nitrobenzamide is used as a precursor in the development of new drugs, agrochemicals, and other biologically active compounds, making it an important intermediate in organic synthesis. Additionally, it has applications in the field of organic chemistry for the creation of diverse molecules with specific properties and functionalities.

InChI:InChI=1/C7H5FN2O3/c8-5-2-1-4(7(9)11)3-6(5)10(12)13/h1-3H,(H2,9,11)

Upstream product

• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 400-94-2 4-fluoro-3-nitrobenzoyl chloride 

Downstream Products

• 1377837-78-9 3-[4-(2,4-Dimethyl-oxazol-5-yl)-thiazol-2-ylamino]-4-isopropoxy-benzamide 
• 1153956-60-5 3-Amino-4-isopropoxy-benzamide 
• 1377581-87-7 4-Isopropoxy-3-isothiocyanato-benzamide 
• 1377581-88-8 4-Isopropoxy-3-thioureido-benzamide 
• 1377581-90-2 4-ethoxy-3-thioureido-benzamide 
• 68502-38-5 4-Benzylamino-3-nitro-benzamide 

Relevant articles and documents

Benzimidazole Derivatives as Potent JAK1-Selective Inhibitors

The Janus kinase (JAK) family comprises four members (JAK1, JAK2, JAK3, and Tyk2) that play a key role in mediating cytokine receptor signaling. JAK inhibition thus modulates cytokine-mediated effects. In particular, selective inhibition of JAK1 or JAK3 may provide an efficient therapeutic agent for the treatment of inflammatory diseases, with minimized side effects. In this study, as part of our continued efforts to develop a selective JAK1 inhibitor, a series of 1,2-disubstituted benzimidazole-5-carboxamide derivatives was prepared and their inhibitory activities against all four JAK isozymes were evaluated. A clear structure-activity relationship was observed with respect to JAK1 selectivity; this highlighted the importance of hydrogen bond donors at both N1 and R2 positions located within a specific distance from the benzimidazole core. One of the synthesized compounds, 1-(2-aminoethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide (5c), showed remarkable JAK1 selectivity (63-fold vs JAK2, 25-fold vs JAK3, and 74-fold vs Tyk2). Molecular docking revealed that the 2-aminoethyl and piperidin-4-yl substituents of 5c function as probes to differentiate the ATP-binding site of JAK1 from that of JAK2, resulting in preferential JAK1 binding. A kinase panel assay confirmed the JAK1 selectivity of 5c, which showed no appreciable inhibitory activity against 26 other protein kinases at 10 μM.

STING AGONISTS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the modulation of STING, and the treatment of STING-mediated disorders.

Novel JAK1-selective benzimidazole inhibitors with enhanced membrane permeability

The previously identified Janus kinase 1 (JAK1)-selective inhibitor, 1-(2-aminoethyl)-2-(piperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide (2), suffered from low cell permeability, which resulted in poor pharmacokinetic properties. In this study, by introducing less polar hydrogen bond donors at N1(a hydroxyalkyl or a methylaminoalkyl group) and C2 (a cyclohexanol group) positions, a series of novel benzimidazole derivatives were prepared, which exhibited selective JAK1 inhibitory activity (IC50against JAK1?=?0.08–0.15?μM; JAK1-selectivity?=?26–40 fold vs JAK2, 12–23 fold vs JAK3, and 38–54 fold vs Tyk2) along with significantly increased lipophilicity (3.3–15.8 times) as well as membrane permeability (6.3–12 times).