1-Hexyl-3-methylimidazolium hexafluorophosphate Chemical Properties

Melting point:

-73.5 °C

Density 

1.3045

refractive index 

n20/D 1.419

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

color 

White

BRN 

8955409

InChI

InChI=1S/C10H19N2.F6P/c1-3-4-5-6-7-12-9-8-11(2)10-12;1-7(2,3,4,5)6/h8-10H,3-7H2,1-2H3;/q+1;-1

InChIKey

YPWSSSRXUOQNMQ-UHFFFAOYSA-N

SMILES

N1(CCCCCC)C=C[N+](C)=C1.[P-](F)(F)(F)(F)(F)F

CAS DataBase Reference

304680-35-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

F 

9-21

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1-Hexyl-3-methylimidazolium hexafluorophosphate Usage And Synthesis

Uses

1-Hexyl-3-methylimidazolium Hexafluorophosphate is a useful research chemical.

Conductivity

0.80 mS/cm (30 °C)

Chemical Properties

Clear colorless to orange liquid

Uses

HMIMPF₆ can be used as a chelate extraction solvent for divalent metal cations using 4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione (thenoyltrifluoroacetone, Htta) as an extractant.

General Description

1-Hexyl-3-methylimidazolium hexafluorophosphate is a water-immiscible imidazolium-type room temperature ionic liquid (RTIL) suitable for electrochemistry.

Synthesis

In a 1L Schlenk flask, 829 g (1.08 mol) of 1-chlorohexane and 260.5 g (2.16 mol) of N-methylimidazole were added, followed by 272.1 g (1.62 mol) of sodium hexafluorophosphate. The reaction mixture was stirred continuously at 70 °C for 2 weeks. Upon completion of the reaction, a white solid product was obtained by filtration through a protective gas glassware. The two phases formed were separated using a partition funnel and the lower yellow phase was collected. The phase was dried overnight at 60°C under high vacuum to give 1-hexyl-3-methylimidazole hexafluorophosphate in 87% yield. To qualitatively detect residual chloride in the product, about 1 ml of the product was mixed with about 5 ml of water and acidified with 2 drops of concentrated nitric acid. To this solution, 3-4 drops of silver nitrate solution were added and observed for the formation of silver chloride precipitate. No precipitate was formed indicating that there was no chloride residue in the product. The structure of the product was confirmed by NMR spectrum: 1H NMR (300 MHz, CDCl3) δ 9.9 (s, 1H, Ha), 7.26 (d, 1H, Hc), 7.24 (d, 1H, Hd), 4.1 (t, 2H, He), 3.9 (s, 2H, Hb), 1.6 (m, 2H, Hf), 1.2 (m, 6H, Hg, h, i) , 0.8 (t, 3H, Hj); 13C NMR (75 MHz, CDCl3) δ 137 (C1), 124-122 (C3, C4), 48 (C5), 35 (C2), 29-24 (C6-C8), 20 (C9), 13 (C10); 31P NMR (121 MHz) δ -143.08 (heptet, J = 710 Hz); 19F NMR (281 MHz) δ -72.5 (d, J = 710 Hz).

References

[1] Tetrahedron Letters, 2003, vol. 44, # 51, p. 9223 - 9224
[2] Patent: EP1182197, 2002, A1. Location in patent: Page 10
[3] Analytical Chemistry, 2004, vol. 76, # 17, p. 5039 - 5044
[4] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3337 - 3340
[5] Journal of Chemical and Engineering Data, 2003, vol. 48, # 3, p. 486 - 491

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