Heptafluorobutyric acid

Heptafluorobutyric acid

Names
IUPAC name 2,2,3,3,4,4,4-Heptafluorobutanoic acid
Other names Heptafluorobutanoic acid; Perfluorobutanoic acid; Perfluorobutyric acid
Identifiers
Abbreviations	HFBA
CAS Registry Number	375-22-4 Y
ChEBI	CHEBI:39426 N
ChemSpider	9394 N
InChI InChI=1S/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13) N Key: YPJUNDFVDDCYIH-UHFFFAOYSA-N N InChI=1/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13) Key: YPJUNDFVDDCYIH-UHFFFAOYAI
Jmol-3D images	Image
PubChem	9777
SMILES OC(C(F)(F)C(F)(F)C(F)(F)F)=O
Properties
Molecular formula	C4HF7O2
Molar mass	214.04 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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

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]

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