Tetrabutylammonium hexafluorophosphate

Tetrabutylammonium hexafluorophosphate Property

Melting point:

244-246 °C (lit.)

Boiling point:

242-246 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

acetonitrile: 0.1 g/mL, clear, colorless

form 

Crystalline Powder and/or Chunks

color 

White to off-white

Sensitive 

Hygroscopic

BRN 

4056584

InChI

InChI=1S/C16H36N.F6P/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-7(2,3,4,5)6/h5-16H2,1-4H3;/q+1;-1

InChIKey

BKBKEFQIOUYLBC-UHFFFAOYSA-N

SMILES

[N+](CCCC)(CCCC)(CCCC)CCCC.[P-](F)(F)(F)(F)(F)F

CAS DataBase Reference

3109-63-5(CAS DataBase Reference)

NIST Chemistry Reference

Tetrabutylammonium hexafluorophosphate(3109-63-5)

EPA Substance Registry System

1-Butanaminium, N,N,N-tributyl-, hexafluorophosphate(1-) (3109-63-5)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37

RIDADR 

1759

WGK Germany 

3

Hazard Note 

Irritant/Hygroscopic

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29239000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

P501Dispose of contents/container to..…

Tetrabutylammonium hexafluorophosphate Chemical Properties,Usage,Production

Chemical Properties

Tetrabutylammonium hexafluorophosphate is a white powder, extremely soluble in polar organic solvents such as acetone and acetonitrile.

Uses

Tetrabutylammonium hexafluorophosphate can be used as a supporting electrolyte for the formation of cyclic disulfide moiety of 3,5-diimido-1,2-dithiolane derivatives by S-S coupling of dithioanilides.

Uses

Tetrabutylammonium hexafluorophosphate (TBAPF₆) or TBAHP can be used:

• As the supporting electrolyte in cyclic voltammetric studies.
• As a reactant in the synthesis of fluorescent nanofibrous sensing films for detecting nitro-explosive vapors.

General Description

Visit our Sensor Applications portal to learn more.

Hazard

Tetrabutylammonium hexafluorophosphate is harmful to humans and is an eye and skin irritant. It may cause severe eye irritation. It may also cause respiratory irritation. Harmful if ingested.

Synthesis

The general procedure for the synthesis of tetrabutylammonium hexafluorophosphate from tetrabutylammonium bromide was as follows: potassium hexafluorophosphate (K[PF6], 2.055 g, 11.2 mmol) was dissolved in 30 mL of deionized water. Tetrabutylammonium bromide ([(n-Bu4)N]Br, 3.601 g, 11.2 mmol) was dissolved in 30 mL of dichloromethane (CH2Cl2) and the resulting solution was subsequently added to the aqueous potassium hexafluorophosphate solution. After stirring the reaction mixture for 24 h at room temperature, phase separation was carried out. The organic phase was washed three times with 10 mL of deionized water, followed by drying with anhydrous sodium carbonate (Na2CO3) and filtration. The filtrate was concentrated by rotary evaporation to give a white solid product. The resulting solid was dried under vacuum at 80 °C for 18 h to give 3.822 g of tetrabutylammonium hexafluorophosphate ([(n-Bu4)N][PF6]) in 88% yield (9.87 mmol). The product characterization data are as follows: differential scanning calorimetry (DSC, 10 K/min): melting point (m.p.) = 250 °C, decomposition temperature (Tdec) = 388 °C. Calculated elemental analysis (measured values): C 49.60% (49.97%), H 9.37% (9.00%), N 3.61% (3.61%).1H NMR (25 °C, CD3CN, 300.13 MHz, δ ppm): 0.96 (t, 12H, CH3), 1.34 (m, 8H, CH3-CH2), 1.59 (m , 8H, CH2-CH2N), 3.06 (m, 8H, NCH2).19F NMR (25 °C, CD3CN, 300.13 MHz, δ ppm): -73.0 (d, 6F, PF6, JP-F = 706.7 Hz).31P NMR (25 °C, CD3CN, 300.13 MHz, δ ppm): - 144.6 (sept, 1P, PF6, JP-F = 706.7 Hz). Infrared spectrum (ATR, 32 scans, ν cm-1): 2966 (m), 2937 (w), 2879 (w), 1472 (m), 1404 (w), 1386 (w), 1360 (w), 1350 (w), 1319 (w), 1260 (w), 1242 (w), 1165 (w), 1109 (w), 1070 (w), 1035 (w), 931 (w), 880 (m), 829 (s), 738 (m), 555 (s).

Purification Methods

Recrystallise it from saturated EtOH/water and dry it for 10hours in a vacuum at 70o. Also recrystallise it three times from absolute EtOH and dry it for 2 days in a drying pistol under a vacuum at boiling toluene temperature [Bedard & Dahl J Am Chem Soc 108 5933 1986]. It is a stable supporting electrolyte in organic solvents [Baiser in Organic Electrochemitry M. Dekker NY p228 1973.]

References

[1] European Journal of Organic Chemistry, 2012, # 19, p. 3566 - 3569
[2] Patent: WO2014/167034, 2014, A2. Location in patent: Page/Page column 48; 49
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 15, p. 4474 - 4477
[4] Angew. Chem., 2015, vol. 127, # 15, p. 4556 - 4559,4
[5] Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4175 - 4188