368426-86-2

Basic information

• Product Name: 5-(Aminomethyl)-2-fluorobenzonitrile
• Synonyms: 5-(aminomethyl)-2-fluorobenzonitrile;Benzonitrile, 5-(aminomethyl)-2-fluoro- (9CI);3-Cyano-4-fluorobenzylamine;5-(AMINOMETHYL)-2-FLUOROBENZONITRILE(WX191678)
• CAS NO: 368426-86-2
• Molecular Formula: C₈H₇FN₂
• Molecular Weight: 150.15
• Product Categories: HALIDE
• Mol File: 368426-86-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 264.2°C
• Flash Point: 114°C
• Appearance: /
• Density: 1.20
• Vapor Pressure: 0.00987mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.51±0.10(Predicted)
• CAS DataBase Reference: 5-(Aminomethyl)-2-fluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(Aminomethyl)-2-fluorobenzonitrile(368426-86-2)
• EPA Substance Registry System: 5-(Aminomethyl)-2-fluorobenzonitrile(368426-86-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 368426-86-2(Hazardous Substances Data)

Usage

Description

5-(Aminomethyl)-2-fluorobenzonitrile is an organic compound characterized by its unique molecular structure, which features a fluorine atom at the 2nd position, an aminomethyl group at the 5th position, and a nitrile group. 5-(Aminomethyl)-2-fluorobenzonitrile is known for its potential applications in various chemical and pharmaceutical processes due to its distinct functional groups and reactivity.

Uses

Used in Pharmaceutical Industry:
5-(Aminomethyl)-2-fluorobenzonitrile is used as a key intermediate in the synthesis of thrombin inhibitors containing P3-heterocycles with P1-bicyclic arginine surrogates. These thrombin inhibitors are crucial in the development of medications for the treatment of various conditions, such as coagulation disorders and cardiovascular diseases, where the regulation of thrombin activity is essential.
In the synthesis process, the compound's fluorine atom and nitrile group provide opportunities for further functionalization and modification, allowing for the creation of diverse thrombin inhibitors with varying potencies and selectivities. The aminomethyl group at the 5th position also plays a significant role in the formation of the desired P3-heterocycles, which are vital for the biological activity of the final product.
Overall, 5-(Aminomethyl)-2-fluorobenzonitrile is a valuable compound in the pharmaceutical industry, particularly in the development of thrombin inhibitors, due to its unique structural features and reactivity. Its applications in this field highlight the importance of understanding and utilizing the properties of organic compounds for the advancement of medical treatments.

InChI:InChI=1/C8H7FN2/c9-8-2-1-6(4-10)3-7(8)5-11/h1-3H,4,10H2

Upstream product

• 368426-85-1 5-(azidomethyl)-2-fluorobenzonitrile 
• 64113-84-4 2-fluoro-5-methylbenzonitrile 
• 180302-35-6 5-bromomethyl-2-fluorobenzonitrile 
• 452-62-0 3-bromo-4-fluorotoluene 

Downstream Products

• 368426-87-3 (3-cyano-4-fluoro-benzyl)-carbamic acid tert-butyl ester 
• 368426-90-8 (3-amino-1H-indazol-5-ylmethyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis and Biological Evaluation of Quinoxaline Derivatives for PET Imaging of the NMDA Receptor

Due to the biological complexity of the N-methyl-d-aspartate receptor (NMDAR), the development of a positron emission tomography radiotracer for the imaging of NMDAR has met with limited success. Recent studies have established the presence of GluN2A subunit of the NMDAR in the heart and its role in the regulation of intracellular calcium levels. In our efforts to develop an imaging agent for the GluN2A subunit, we designed three new compounds based on a quinoxaline scaffold. The synthesis of the analogues was based on a two-step Kabachnik–Fields reaction in sequence with Suzuki cross-coupling and acid hydrolysis. They exhibited comparable high binding affinity values below 5 nm. A two-step radiolabeling procedure was successfully developed for the synthesis of [18F]1. [18F]1 was obtained in a modest overall radiochemical yield of 5.5 ± 4.2%, a good specific radioactivity of 254 ± 158 GBq/μmol, and a radiochemical purity > 99%. While compounds 2 and 3 showed comparable binding affinity towards NMDAR, sluggish radiolabeling, prevented their further evaluation. For [18F]1, in vitro autoradiography on rat heart slices demonstrated heterogeneous but unspecific accumulation, whereas for the brain a high in vitro specificity towards NMDAR, could be demonstrated.

Non-covalent thrombin inhibitors featuring P3-heterocycles with P1-bicyclic arginine surrogates

Novel, potent, and highly selective classes of thrombin inhibitors were identified, which resulted from judicious combination of P4-aromatics and P2-P3-heterocyclic dipeptide surrogates with weakly basic (calcd pKa ～non-basic - 8.6) bicyclic P1-arginine mimics. The design, synthesis, and biological activity of achiral, non-covalent, orally bioavailable inhibitors NC1-NC44 featuring P1-indazoles, benzimidazoles, indoles, benzotriazoles, and aminobenzisoxazoles is disclosed.