(S)-1-(4-FLUOROPHENYL)ETHYLAMINE Chemical Properties

Melting point:

-30°C

Boiling point:

76°C 22mm

Density 

1,03 g/cm³

refractive index 

1.501

Flash point:

76°C/22mm

storage temp. 

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

solubility 

Miscible with dimethyl sulfoxide.

pka

8.98±0.10(Predicted)

form 

liquid

color 

Clear

optical activity

Consistent with structure

Sensitive 

Air Sensitive

BRN 

6791614

CAS DataBase Reference

66399-30-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,C

Risk Statements 

34-51/53-22

Safety Statements 

26-36/37/39-61-45

RIDADR 

2735

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

2921490090

MSDS

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(S)-1-(4-FLUOROPHENYL)ETHYLAMINE Usage And Synthesis

Chemical Properties

Colorless transparent liquid

Uses

(S)-(-)-1-(4-Fluorophenyl)ethylamine is used in organic synthesis. It acts as a ligand and form a coordination complex, diacetato-2-O-bis[(S)-1-(4-fluorophenyl)ethylamine-N]palladium(II) by reacting with palladium(II) acetate.

Synthesis

General procedure for the synthesis of (S)-1-(4-fluorophenyl)ethylamine using 4-fluoroacetophenone as starting material: to a vial containing 4-fluoroacetophenone (0.2 mmol, 1.0 eq.), ammonium formate (HCO2NH4, 37.8 mg, 2 mmol, 10.0 eq.), and Pdα-nanocatalyst (Pd°-AmP-MFC, 2.68 mg. 0.002 mmol, 8 wt%) were added to the vial with methanol (0.3 mL) and the reaction mixture was stirred for the time indicated in Table 4. Upon completion of the reaction, the vials were cooled in an ice bath, followed by the addition of methanol (0.367 mL) and a buffer solution (50 mM HEPES, pH 8.2, 6 mL) containing aminotransferase (ATA) and 2-5 equivalents of sodium pyruvate (1 equivalent = 0.2 mmol, 22 mg). The reaction tubes were placed under light-avoiding conditions and left to stand at room temperature for 24 h with gentle shaking on an orbital oscillator. Upon completion of the reaction, the enantiomeric excess (ee) of the product was determined by high performance liquid chromatography (HPLC) analysis (repeated three times for each sample).

References

[1] Patent: WO2016/96905, 2016, A1. Location in patent: Page/Page column 25
[2] Chemistry Letters, 2004, vol. 33, # 11, p. 1424 - 1425
[3] Journal of Organic Chemistry, 2013, vol. 78, # 11, p. 5314 - 5327
[4] Organic Process Research and Development, 2014, vol. 18, # 6, p. 788 - 792
[5] ACS Catalysis, 2016, vol. 6, # 6, p. 3932 - 3940

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