1-Fluoro-2,4-dinitrobenzene

• Catalog No.: A11871
• CAS Number: 70-34-8
• M. F.: C6H3FN2O4
• M. W.: 186.0974232
• Purity: 99%

SYNONYMS

• Title: 2,4-二硝基-1-氟苯
• IUPAC name: 1-fluoro-2,4-dinitrobenzene
• IUPAC Traditional name: dinitrofluorobenzene
• Synonyms: Sanger's Reagent; 2,4-Dinitrofluorobenzene

DATABASE IDS

• Beilstein Number: 398632
• CAS Number: 70-34-8
• Merck Index: 144172
• EC Number: 200-734-3
• MDL Number: MFCD00007056

PROPERTIES

• Purity: 99%
• RTECS: CZ7800000
• Safety Statements: 24-26-36/37/39-45
• GHS Hazard statements: H301-H311-H331-H315-H317-H318-H341
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P361-P405-P501A
• Risk Statements: 23/24/25-38-41-43-68
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2811
• Packing Group: III
• Boiling Point: 296°C
• Density: 1.482
• Flash Point: >110°C(230°F)
• Melting Point: 24-30°C
• Refractive Index: 1.5690

REFERENCES

• Has been used as a means of protection for the thiol group. The resulting thioether can be cleaved quantitatively with 2-mercaptoethanol: Biochem. Biophys. Res. Commun., 29, 178 (1967).
• Can also be used for the masking of the imidazole ring in histidine as the 2,4-dinitrophenyl derivative during peptide synthesis, introduced in the presence of, e.g. K₂CO₃: Biochem. Biophys. Acta., 82, 412 (1964). The group can be cleaved by treatment with thioglycolic acid, mercaptoethanol, dithiothreitol or thiophenol: Biochem. Biophys. Res. Commun., 29, 178 (1967); Biochemistry, 9, 5122 (1970). The electron withdrawing character of the group has been shown to reduce racemization promoted by the imidazole function: J. Biol. Chem., 247, 4768 (1972). See Appendix 6.
• The activated fluoro-substituent is readily displaced by nucleophiles under mild conditions. The anomeric center of a carbohydrate has been protected as the 2,4-dinitrophenyl ether in the presence of DABCO in DMF: Rec. Trav. Chim., 99, 355 (1980).
• Used for labelling terminal amino acids in peptides: Biochem. J., 45, 563 (1949); Biochemistry, 20, 512 (1981).