93246-53-8 | 3-FLUORO-4-MORPHOLIN-4-YL-PHENYLAMINE

CAS:93246-53-8 | 3-FLUORO-4-MORPHOLIN-4-YL-PHENYLAMINE,Description

3-Fluoro-4-morpholinoaniline is a member of morpholines. It has a fluorinated aniline linked to a morpholine, a heterocycle featuring both amine and ether groups. The molecular formula is C10H13FN2O.

Synthesis Analysis

The precursor compound 3-fluoro-4-morpholinoaniline is an important intermediate of the antibiotic drug linezolid. It was synthesized initially by the substitution of morpholine on 1,2-difluoro-4-nitrobenzene under neat conditions. Novel morpholine and its sulfonamide derivatives were designed and synthesized as potential anti-tumor agents.

Molecular Structure Analysis

The IUPAC name of 3-Fluoro-4-morpholinoaniline is 3-fluoro-4-morpholin-4-ylaniline. The InChI is InChI=1S/C10H13FN2O/c11-9-7-8(12)1-2-10(9)13-3-5-14-6-4-13/h1-2,7H,3-6,12H2. The Canonical SMILES is C1COCCN1C2=C(C=C(C=C2)N)F.

Chemical Reactions Analysis

By having the accessible primary amine, 3-fluoro-4-morpholinoaniline reacts with aldehyde to form Schiff bases. A series of new sulfonamides and carbamates have been synthesized in good yields by the reaction of substituted aryl sulfonyl chlorides and substituted aryl/acyclic chloroformates with the precursor compound.

Physical And Chemical Properties Analysis

The molecular weight of 3-Fluoro-4-morpholinoaniline is 196.22 g/mol. The density is 1.2±0.1 g/cm3, and the boiling point is 364.9±42.0 °C at 760 mmHg. The vapour pressure is 0.0±0.8 mmHg at 25°C, and the enthalpy of vaporization is 61.1±3.0 kJ/mol.

Scientific Research Applications

Synthesis and Antimicrobial Activity

3-Fluoro-4-morpholinoaniline is a key intermediate in the synthesis of various pharmaceutical compounds. A study by Janakiramudu et al. (2017) describes its use in the creation of sulfonamides and carbamates, showing significant antimicrobial activity. This demonstrates the compound's potential in developing new antimicrobial agents.

Role in Linezolid Synthesis

The compound plays a crucial role in the synthesis of linezolid, an antibiotic drug. Basoglu et al. (2012) explored its conversion to various derivatives, revealing good antitubercular activities. This indicates its importance in tuberculosis treatment research.

Antitumor and Antiviral Applications

In the field of cancer and viral infections, research has shown promising results. Hao et al. (2017) synthesized a compound using 3-Fluoro-4-morpholinoaniline that inhibits the proliferation of certain cancer cell lines. Similarly, Ivachtchenko et al. (2019) developed a molecule for inhibiting hepatitis B, highlighting its potential in antiviral research.

Electrochemical Studies

The electrochemical properties of derivatives of 3-Fluoro-4-morpholinoaniline have been studied, indicating its potential in material science. For example, Esmaili and Nematollahi (2011) investigated the electrochemical oxidation of 4-morpholinoaniline, paving the way for new material synthesis methods.

Anti-Inflammatory Properties

In the field of anti-inflammatory drug development, Honavar et al. (2020) synthesized carboxamides from 3-fluoro-4-morpholinoaniline and tested them for anti-inflammatory activity. This research opens new avenues in developing anti-inflammatory medications.

Safety And Hazards

Users should avoid dust formation, breathing mist, gas or vapours, and contacting with skin and eye. Personal protective equipment should be used, and adequate ventilation should be ensured.

Future Directions

The dihydropyranoindole structures were previously identified as promising scaffolds for improving the anti-cancer activity of histone deacetylase inhibitors. Low concentrations of newly synthesized BuTD-CH could be safely used as an antimicrobial and pharmacological agent for inhibiting the growth of human pathogenic microbes and hepatocellular and adenocarcinoma therapy.

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