Perfluorobutanoic acid

{{Hatnote|HFBA can also refer to Hebrew Free Burial Association}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 421609225

| ImageFile = Heptafluorobutyric acid.png

| ImageSize = 150px

| ImageAlt = Skeletal formula

| ImageFile1 = Perfluorobutyric-acid-3D-balls.png

| ImageSize1 = 160

| ImageAlt1 = Ball-and-stick model

| PIN = Heptafluorobutanoic acid

| OtherNames = Perfluorobutanoic acid
Perfluorobutyric acid
Heptafluorobutyric acid
HFBA
PFBA{{Cite journal |last=Buck |first=Robert C |last2=Franklin |first2=James |last3=Berger |first3=Urs |last4=Conder |first4=Jason M |last5=Cousins |first5=Ian T |last6=de Voogt |first6=Pim |last7=Jensen |first7=Allan Astrup |last8=Kannan |first8=Kurunthachalam |last9=Mabury |first9=Scott A |last10=van Leeuwen |first10=Stefan PJ |date=2011 |title=Perfluoroalkyl and polyfluoroalkyl substances in the environment: Terminology, classification, and origins |journal=Integrated Environmental Assessment and Management |language=en |volume=7 |issue=4 |pages=513–541 |doi=10.1002/ieam.258 |pmc=3214619 |pmid=21793199}}
C₄ PFCA

|Section1={{Chembox Identifiers

| Abbreviations = HFBA

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 375-22-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 12VHZ8L29I

| PubChem = 9777

| SMILES = OC(C(F)(F)C(F)(F)C(F)(F)F)=O

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 9394

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 39426

| InChI = 1/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13)

| InChIKey = YPJUNDFVDDCYIH-UHFFFAOYAI

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YPJUNDFVDDCYIH-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C =4|H=1|F=7|O=2

| Appearance = colourless liquid

| Density = 1.64 g/ml

| MeltingPt =

| BoilingPtC = 120

| Solubility = high}}

|Section3={{Chembox Hazards

| Hazards_ref =

| GHS_ref = {{Sigma-Aldrich|SIGMA|id=77249|name=Heptafluorobutyric acid|accessdate=2022-03-23}}

| GHSPictograms = {{GHS05}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|314}}

| PPhrases = {{P-phrases|260|280|303+361+353|304+340+310|305+351+338}}

| MainHazards = strong acid

| FlashPt =

| AutoignitionPt =

}}

}}

Perfluorobutanoic acid (PFBA) is a perfluoroalkyl carboxylic acid with the formula C₃F₇CO₂H. As the perfluorinated derivative of butyric acid, this colourless liquid is prepared by electrofluorination of the corresponding butyryl fluoride.{{Citation |last=Siegemund |first=Günter |title=Fluorine Compounds, Organic |date=2000 |work=Ullmann's Encyclopedia of Industrial Chemistry |pages= |place=Weinheim, Germany |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |language=en |doi=10.1002/14356007.a11_349 |isbn=978-3-527-30673-2 |last2=Schwertfeger |first2=Werner |last3=Feiring |first3=Andrew |last4=Smart |first4=Bruce |last5=Behr |first5=Fred |last6=Vogel |first6=Herward |last7=McKusick |first7=Blaine}}

== Applications ==

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

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

PFBA was formerly used for manufacturing photographic film. The 3M Company was a major manufacturer of PFBA and products containing PFBA but production was phased out in 1998.{{cite web |title=Perfluorobutanoic acid (PFBA) and Water |url=https://www.health.state.mn.us/communities/environment/risk/docs/guidance/gw/pfbainfo.pdf |publisher=Minnesota Department of Health|date=April 2022 |access-date=8 September 2023}}