2-((2,4-DiMethylphenyl)thio)phenylaMine Chemical Properties

Boiling point:

341.3±30.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Sparingly), Methanol (Sparingly)

pka

3.12±0.10(Predicted)

form 

Oil to Semi-Solid

color 

Dark Brown to Very Dark Red

Stability:

Hygroscopic

2-((2,4-DiMethylphenyl)thio)phenylaMine Usage And Synthesis

Uses

2-[(2,4-Dimethylphenyl)sulfanyl]aniline is used in the study of N-O-glucuronide metabolites of Lu AA21004 (Vortioxetine [V766000]), an antidepressant.

Synthesis

Using 4-iodo-m- dimethylbenzene (1.43 mL, 10.0 mmol) and 2-aminothiophenol (1.07 mL, 10.0 mmol) as raw materials, the above raw materials were mixed with cuprous iodide (0.19 g, 1.0 mmol), potassium carbonate (6.90 g, 50.0 mmol) and dried and degassed dimethylsulfoxide (50 mL) under nitrogen protection at 120 °C for 16 h with stirring. After completion of the reaction, the mixture was cooled to room temperature, diluted with water (50 mL) and the product was extracted with ethyl acetate (2 x 150 mL). The organic layers were combined and washed sequentially with water (3 x 150 mL) and brine (3 x 150 mL). The organic phase was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure to afford 2-((2,4-dimethylphenyl)thio)aniline as a dark colored oil (2.15 g, 94% yield). The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3, 500 MHz) and mass spectrometry (ESI): 1H NMR δ 2.28 (s, 3H), 2.40 (s, 3H), 4.24 (br s, 2H), 6.71 (d, J = 8.1 Hz, 1H), 6.75-6.81 (m, 2H), 6.87 (m, 1H) 7.02 (m, 1H), 7.23 (m, 1H), 7.38 (dd, J = 1.5, 7.7 Hz, 1H); MS (ESI) m/z: 230 [MH]+.

References

[1] Patent: WO2015/155153, 2015, A1. Location in patent: Page/Page column 15

2-((2,4-DiMethylphenyl)thio)phenylaMine(1019453-85-0)Related Product Information

• Vortioxetine Impurity 4
• 3,5-DIMETHYLTHIOPHENOL
• 1-[(2-Bromophenyl)thio]-2,4-dimethylbenzene
• Vortioxetine impurity S
• BIS(2-BROMOETHYL)AMINE HYDROBROMIDE
• Vortioxetine Impurity 37 HCl
• 1,2-Bis(piperazin-1-yl)benzene
• Vortioxetine Impurity 2
• 1-[2-[(5-chloro-2,4-diMethylphenyl)thio]phenyl]- Piperazine
• 1-(2-BROMOPHENYL)PIPERAZINE
• 2,4-Dimethylbenzenethiol
• 3,4-DIMETHYLTHIOPHENOL
• 1-[2-[(2,4-diMethylphenyl)sulfinyl]phenyl]- Piperazine
• di(2,4-xylyl) disulphide
• 1-[2-[(2,4-diMethylphenyl)thio]phenyl]-4-[2-(1-piperazinyl)phenyl]- Piperazine
• Vortioxetine hydrobromide
• 2,4-DIMETHYLDIPHENYLSULFIDE
• Vortioxetine Impurity 1