Heptafluorobutyric acid

Heptafluorobutyric acid (HFBA) is an organofluorine compound with the formula C₃F₇CO₂H. As the fluorinated derivative of butyric acid, this colourless liquid is prepared by electrofluorination of the corresponding butyryl fluoride.[1]

Heptafluorobutyric acid

Names
IUPAC name 2,2,3,3,4,4,4-Heptafluorobutanoic acid
Other names Heptafluorobutanoic acid; Perfluorobutanoic acid; Perfluorobutyric acid; PFBA
Identifiers
CAS Number	375-22-4
3D model (JSmol)	Interactive image
Abbreviations	HFBA
ChEBI	CHEBI:39426
ChemSpider	9394
ECHA InfoCard	100.006.170
PubChem CID	9777
UNII	12VHZ8L29I
CompTox Dashboard (EPA)	DTXSID4059916
InChI InChI=1S/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13) Key: YPJUNDFVDDCYIH-UHFFFAOYSA-N InChI=1/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13) Key: YPJUNDFVDDCYIH-UHFFFAOYAI
SMILES OC(C(F)(F)C(F)(F)C(F)(F)F)=O
Properties
Chemical formula	C4HF7O2
Molar mass	214.039 g·mol^−1
Appearance	colourless liquid
Density	1.64 g/ml
Boiling point	120 °C (248 °F; 393 K)
Solubility in water	high
Hazards
Main hazards	strong acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Applications

HFBA has a variety of niche applications in analytical and synthetic chemistry. It is an ion pair reagent for reverse-phase HPLC. It is used in the sequencing, synthesis, and solubilizing of proteins and peptides.

Esters derived from HFBA readily undergo condensation, owing to their electrophilicity. Specialized ligands for metal ions are generated capitalizing on this property, such as Eufod.

References

1. Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick "Fluorine Compounds, Organic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a11_349