3-FLUORO-DL-PHENYLALANINE Chemical Properties

Melting point:

~240 °C (dec.)

Boiling point:

305.0±32.0 °C(Predicted)

Density 

1.1939 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

2.17±0.10(Predicted)

color 

White to Almost white

BRN 

2939807

CAS DataBase Reference

456-88-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37

Safety Statements 

24/25

RIDADR 

UN2811

WGK Germany 

3

RTECS 

AY6300000

HazardClass 

6.1

HS Code 

2922498590

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-FLUORO-DL-PHENYLALANINE Usage And Synthesis

Uses

cell analysis
peptide synthesis

Biological Activity

m-Fluoro-DL-phenylalanine, a toxic antimetabolite, is a racemic mixture of a substituted (halogenated) benzoyl D and L phenylalanine with potential use in antiviral and antimicrobial drug development.

Synthesis

General procedure for the synthesis of 3-fluoro-DL-phenylalanine from compound (CAS: 380-70-1): intermediate 231 (7.50 g, 21.43 mmol) was added to 94% hydrochloric acid (80 mL). The reaction mixture was stirred under reflux conditions for 15 h. The completion of the reaction was confirmed by TLC analysis. After completion of the reaction, the mixture was filtered to give white solid 233 in 86% yield. High resolution mass spectrometry (HRMS, ESI) analysis resulted in a calculated value of 184.0715 (M + H)+ for m/z, C9H10NO2 and a measured value of 184.0767.

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1325 - 1344
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 1806
[3] Organic Letters, 2018, vol. 20, # 19, p. 6298 - 6301

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