4-FLUORO-2-IODOBENZOIC ACID Chemical Properties

Melting point:

143-147 °C

Boiling point:

309.4±27.0 °C(Predicted)

Density 

2.074±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Ethyl Acetate (Slightly), Methanol (Slightly)

pka

2.80±0.10(Predicted)

form 

Solid

color 

White

Sensitive 

Light Sensitive

InChIKey

DUKFTVLJAXWGPI-UHFFFAOYSA-N

CAS DataBase Reference

56096-89-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-36/37/38

Safety Statements 

26-36/37-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

29163990

4-FLUORO-2-IODOBENZOIC ACID Usage And Synthesis

Chemical Properties

Off-white crystalline

Uses

4-Fluoro-2-iodobenzoic Acid is a reagent used in organic synthesis including amixile-based inhibitors of the pyruvate-ferredoxin oxidoreductases of anaerobic bacteria.

Synthesis

Synthesis of 4-fluoro-2-iodobenzoic acid (11): 4-fluoro-2-iodobenzaldehyde (10) (2.82 g, 11.3 mmol) was dissolved in a mixed solvent of H2O (500 mL) and acetone (90 mL), to which were added sequentially H2NSO3H (1.59 g, 16.4 mmol) and NaClO2 (1.78 g, 15.7 mmol, technical grade (80% purity). The reaction mixture was stirred at room temperature for 3.5 h. The progress of the reaction was monitored by thin layer chromatography (TLC) until complete consumption of the ingredients. Upon completion of the reaction, the aqueous phase was extracted with ethyl acetate (EtOAc, 4×), the organic phases were combined, washed with saturated saline, and concentrated under reduced pressure to afford the colorless solid product 11 (2.55 g, 9.6 mmol, 85% yield). The product was characterized by the following data: melting point 155-157 °C; TLC Rf = 0.5 (CHCl3-MeOH = 10:1, v/v); IR (KBr, cm-1): 3436 (br), 3070 (br), 1701 (s), 1588 (s), 1575 (s), 1477 (m), 1413 (m), 1303 (s). 1260 (s), 1206 (s), 1030 (m), 874 (m), 605 (m); 1H NMR (300 MHz, CD3OD): δ 7.23-7.29 (m, 1H), 7.82 (dd, 3JHF = 8.4 Hz, 4JHH = 2.6 Hz, 1H), 7.90 (dd, 3JHH = 8.7 Hz, 4JHH = 2.6 Hz, 1H), 7.90 (dd, 3JHH = 8.7 Hz, 4JHH = 6.0 Hz), 7.90 (dd, 3JHH = 8.7 Hz, 4JHH = 2.6 Hz, 1H) 4JHF = 6.0 Hz, 1H); 13C NMR (75.5 MHz, CD3OD): δ 95.4 (d, 3JCF = 8.5 Hz), 116.4 (d, 2JCF = 21.7 Hz), 129.7 (d, 2JCF = 24.1 Hz), 133.8 (d, 4JCF = 3.5 Hz), 134.0 (d, 3JCF = 9.1 Hz), 164.9 (d, 1JCF = 255.7 Hz), 169.0; MS (EI) m/z (relative intensities): 267 (27) [M+ + H], 266 (100) [M+], 249 (75) [C7H3OFI+], 221 (13) [C6H3FI+], 127 (2) [I+]. 122 (3) [C7H3OF+], 94 (17) [C6H3F+]; HRMS (EI) calculated value C7H4O2FI [M+] 265.9240, measured value 249.9258.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5445 - 5447

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