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

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

Uses

Used in Pharmaceutical Industry:
4-Fluoro-3-nitrobenzamide is used as a precursor in the development of new drugs, making it an important intermediate in organic synthesis. Its unique structure with a fluorine atom and a nitro group allows for the creation of diverse molecules with specific properties and functionalities, contributing to the discovery of novel therapeutic agents.
Used in Research Industry:
In the research field, 4-Fluoro-3-nitrobenzamide serves as a valuable building block for the synthesis of various organic compounds. Its presence in the benzene ring with the fluorine and nitro substituents enables the exploration of new chemical reactions and the generation of molecules with potential applications in various research areas.
Used in Agrochemical Industry:
4-Fluoro-3-nitrobenzamide is also utilized as a precursor in the development of agrochemicals, contributing to the creation of new compounds with potential applications in agriculture, such as pesticides and herbicides. Its unique structure allows for the design of molecules with specific target sites and improved efficacy in controlling pests and weeds.
Used in Organic Chemistry:
In the field of organic chemistry, 4-Fluoro-3-nitrobenzamide has applications in the creation of diverse molecules with specific properties and functionalities. Its presence in the benzene ring with the fluorine and nitro substituents enables the exploration of new chemical reactions and the generation of molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

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

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

Downstream Products

• 68502-38-5 4-Benzylamino-3-nitro-benzamide 
• 912369-47-2 tert-butyl (3S)-3-[4-(aminocarbonyl)-2-nitrophenoxy]piperidine-1-carboxylate 
• 1369838-81-2 4-Isopropoxy-3-nitro-benzamide 
• 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 
• 1377977-48-4 4-Isopropoxy-3-(4-pyridin-2-yl-thiazol-2-ylamino)-benzamide 
• 1415819-68-9 C₂₄H₂₆FN₅O₃S 
• 1415820-46-0 4-fluoro-3-nitrobenzothioamide 
• 1415820-47-1 methyl 4-(2-(4-fluoro-3-nitrophenyl)thiazol-4-yl)-1H-pyrrole-2-carboxylate 
• 1415820-48-2 methyl 4-(2-(3-amino-4-fluorophenyl)thiazol-4-yl)-1H-pyrrole-2-carboxylate 
• 1415820-49-3 C₁₇H₁₃ClFN₃O₃S 
• 1415820-50-6 methyl 4-(2-(4-fluoro-3-(2-morpholinoacetamido)phenyl)thiazol-4-yl)-1H-pyrrole-2-carboxylate 

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.

Discovery and Optimization of Potent, Selective, and in Vivo Efficacious 2-Aryl Benzimidazole BCATm Inhibitors

To identify BCATm inhibitors suitable for in vivo study, Encoded Library Technology (ELT) was used to affinity screen a 117 million member benzimidazole based DNA encoded library, which identified an inhibitor series with both biochemical and cellular activities. Subsequent SAR studies led to the discovery of a highly potent and selective compound, 1-(3-(5-bromothiophene-2-carboxamido)cyclohexyl)-N-methyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamide (8b) with much improved PK properties. X-ray structure revealed that 8b binds to the active site of BACTm in a unique mode via multiple H-bond and van der Waals interactions. After oral administration, 8b raised mouse blood levels of all three branched chain amino acids as a consequence of BCATm inhibition.

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.

HETEROCYCLIC AMIDES USEFUL AS PROTEIN MODULATORS

Disclosed are compounds having the formula (I) wherein Ra, R1, R2, R3, R4, R5, R6, R7, and R8, are as defined herein, or a salt, particularly a pharmaceutic

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).

BENZOIMIDAZOLE DERIVATIVES SELECTIVELY INHIBITING THE ACTIVITY OF JANUS KINASE 1

The present invention relates to a benzimidazole derivative having activity which selectively inhibits activity of janus kinase 1 and a use as an immunosuppressant of the compound.COPYRIGHT KIPO 2016

BIS HETEROARYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables A, Q, J, R1, R3, and R5 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

FUSED HETEROARYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables A, Q, J, R1, R3, and R5 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

PYRIDYL-THIAZOLYL INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to thiazole I and its therapeutic and prophylactic uses, wherein the variables Rz, Q, J, R1, R3, R5, and R6 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.

BISTHIAZOLE INHIBITORS OF PRO-MATRIX METALLOPROTEINASE ACTIVATION

This invention relates to bisthiazole I and its therapeutic and prophylactic uses, wherein the variables A, R5, R6, and R7 are defined in the specification. Disorders treated and/or prevented include rheumatoid arthritis.