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1-Butyl-3-methylimidazolium hexafluorophosphate ([C4mim][PF6] or bmimPF6) is an ionic liquid that serves as an effective solvent medium for studying ligand substitution reactions, particularly in homogeneous catalysis. It promotes the formation of charge-separated products in reactions involving the displacement of anionic ligands by neutral molecules, such as pyridine derivatives, demonstrating superior performance compared to traditional solvents like dichloromethane. Its weak coordinating ability and ability to enhance reaction selectivity make it a valuable alternative in catalytic processes where anionic ligands compete for coordination sites.

174501-64-5

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174501-64-5 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 174501-64-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,4,5,0 and 1 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 174501-64:
(8*1)+(7*7)+(6*4)+(5*5)+(4*0)+(3*1)+(2*6)+(1*4)=125
125 % 10 = 5
So 174501-64-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H16N2.F6P/c1-3-4-5-10-7-6-9(2)8-10;1-7(2,3,4,5)6/h6-7H,3-5,8H2,1-2H3;/q;-1/p+1

174501-64-5 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (B2320)  1-Butyl-3-methylimidazolium Hexafluorophosphate  >98.0%(HPLC)(N)

  • 174501-64-5

  • 5g

  • 280.00CNY

  • Detail
  • TCI America

  • (B2320)  1-Butyl-3-methylimidazolium Hexafluorophosphate  >98.0%(HPLC)(N)

  • 174501-64-5

  • 25g

  • 790.00CNY

  • Detail
  • Alfa Aesar

  • (L19086)  1-n-Butyl-3-methylimidazolium hexafluorophosphate, 98+%   

  • 174501-64-5

  • 5g

  • 858.0CNY

  • Detail
  • Alfa Aesar

  • (L19086)  1-n-Butyl-3-methylimidazolium hexafluorophosphate, 98+%   

  • 174501-64-5

  • 25g

  • 1786.0CNY

  • Detail
  • Alfa Aesar

  • (L19086)  1-n-Butyl-3-methylimidazolium hexafluorophosphate, 98+%   

  • 174501-64-5

  • 100g

  • 2518.0CNY

  • Detail
  • Sigma-Aldrich

  • (18122)  1-Butyl-3-methylimidazoliumhexafluorophosphate  for catalysis, ≥98.5% (T)

  • 174501-64-5

  • 18122-5G-F

  • 2,322.45CNY

  • Detail
  • Sigma-Aldrich

  • (18122)  1-Butyl-3-methylimidazoliumhexafluorophosphate  for catalysis, ≥98.5% (T)

  • 174501-64-5

  • 18122-50G-F

  • 14,660.10CNY

  • Detail
  • Aldrich

  • (70956)  1-Butyl-3-methylimidazoliumhexafluorophosphate  ≥97.0% (HPLC)

  • 174501-64-5

  • 70956-5G

  • 868.14CNY

  • Detail
  • Aldrich

  • (70956)  1-Butyl-3-methylimidazoliumhexafluorophosphate  ≥97.0% (HPLC)

  • 174501-64-5

  • 70956-50G

  • 2,127.06CNY

  • Detail
  • Aldrich

  • (70956)  1-Butyl-3-methylimidazoliumhexafluorophosphate  ≥97.0% (HPLC)

  • 174501-64-5

  • 70956-250G

  • 7,034.04CNY

  • Detail

174501-64-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Butyl-3-methylimidazolium hexafluorophosphate

1.2 Other means of identification

Product number -
Other names 1-butyl-3-methylimidazolium hexafluorophosphate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:174501-64-5 SDS

174501-64-5Synthetic route

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With sodium hexaflorophosphate In acetone at 80℃; for 0.166667h; microwave irrradiation;99%
With potassium hexafluorophosphate In acetone at 20℃; for 24h;98%
1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In water at 20℃;100%
With ammonium hexafluorophosphate In water at 20℃; for 2h;91%
With potassium hexafluorophosphate In water at 20℃; for 24h;87%
1-methyl-3-(n-butyl)imidazolium iodide
65039-05-6

1-methyl-3-(n-butyl)imidazolium iodide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With Amberlist A-26 BF6(-) form In methanol Ionic liquid;
1-Butylimidazole
4316-42-1

1-Butylimidazole

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With ammonium hexafluorophosphate Reagent/catalyst; Schlenk technique; Reflux;95%
With ammonium hexafluorophosphate at 110℃; for 17h; Reagent/catalyst; Inert atmosphere;88%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-bromo-butane
109-65-9

1-bromo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 40 - 120℃; for 0.166667h; microwave irradiation; sonication;94%
With potassium hexafluorophosphate at 80℃; for 3.5h;93%
With ammonium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 15h;89%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-Butyl chloride
109-69-3

n-Butyl chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate at 70℃; for 336h;92%
Stage #1: 1-methyl-1H-imidazole; n-Butyl chloride In toluene for 48h; Reflux;
Stage #2: With potassium hexafluorophosphate In toluene
92%
With potassium hexafluorophosphate at 120 - 180℃; for 0.75h; microwave irradiation;90%
1-Butylimidazole
4316-42-1

1-Butylimidazole

dimethyl sulfate
77-78-1

dimethyl sulfate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; dimethyl sulfate for 0.25h;
Stage #2: With sodium hexaflorophosphate In water
92%
1-butyl-3-methylimidazolium chloride

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In acetone for 24h;90%
methanol
67-56-1

methanol

N-methyl-N'-n-butylimidazolium-2-carboxylate
671779-18-3

N-methyl-N'-n-butylimidazolium-2-carboxylate

A

potassium monomethylcarbonate
14660-45-8

potassium monomethylcarbonate

B

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 20℃; for 12h;A 87%
B 72%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-iodo-butane
542-69-8

1-iodo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 10h;85%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;75%
potassium fluoride

potassium fluoride

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

Trimethyl borate
121-43-7

Trimethyl borate

hydrogen fluoride
7664-39-3

hydrogen fluoride

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

A

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

B

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

C

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

D

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: potassium fluoride; N-trimethylsilyl-tris(pentafluorethyl)phosphazen; Trimethyl borate In 1,2-dimethoxyethane at 20 - 60℃; for 1h;
Stage #2: hydrogen fluoride In 1,2-dimethoxyethane; water at 0 - 20℃; for 3h;
Stage #3: 1-butyl-3-methylimidazolium chloride In water
A 60%
B 30%
C 6%
D 4%
1-Butylimidazole
4316-42-1

1-Butylimidazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; carbonic acid dimethyl ester In methanol at 135℃; for 7h;
Stage #2: With sodium hexaflorophosphate In methanol; acetone at 25℃; for 2h;
52%
1-Butylimidazole
4316-42-1

1-Butylimidazole

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 - 70 °C
2: NH4PF6
View Scheme
hexafluorophosphate anion

hexafluorophosphate anion

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
at 20℃;
formaldehyd
50-00-0

formaldehyd

Glyoxal
131543-46-9

Glyoxal

N-butylamine
109-73-9

N-butylamine

methylamine
74-89-5

methylamine

A

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

B

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

C

1,3-di-n-butylimidazolium hexafluorophosphate

1,3-di-n-butylimidazolium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: formaldehyd; N-butylamine; methylamine In water at 0℃;
Stage #2: With hexafluorophosphoric acid In water at 0℃;
Stage #3: Glyoxal In water at 0 - 20℃;
1-butyl-3-methylimidazolium halide

1-butyl-3-methylimidazolium halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-butyl halide

n-butyl halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With alkali metal hexafluorophosphate at 150℃; for 0.5h; Microwave irradiation; Cooling; neat (no solvent);
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water at 20℃; for 24h;
sodium hexaflorophosphate

sodium hexaflorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water
Ionic liquid; Inert atmosphere;
1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With sodium hexaflorophosphate In acetone at 80℃; for 0.166667h; microwave irrradiation;99%
With potassium hexafluorophosphate In acetone at 20℃; for 24h;98%
1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In water at 20℃;100%
With ammonium hexafluorophosphate In water at 20℃; for 2h;91%
With potassium hexafluorophosphate In water at 20℃; for 24h;87%
1-methyl-3-(n-butyl)imidazolium iodide
65039-05-6

1-methyl-3-(n-butyl)imidazolium iodide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With Amberlyst A-26 (PF6- form) In methanol100%
With Amberlist A-26 BF6(-) form In methanol Ionic liquid;
1-Butylimidazole
4316-42-1

1-Butylimidazole

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With ammonium hexafluorophosphate Reagent/catalyst; Schlenk technique; Reflux;95%
With ammonium hexafluorophosphate at 110℃; for 17h; Reagent/catalyst; Inert atmosphere;88%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-bromo-butane
109-65-9

1-bromo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 40 - 120℃; for 0.166667h; microwave irradiation; sonication;94%
With potassium hexafluorophosphate at 80℃; for 3.5h;93%
With ammonium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 15h;89%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-Butyl chloride
109-69-3

n-Butyl chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate at 70℃; for 336h;92%
Stage #1: 1-methyl-1H-imidazole; n-Butyl chloride In toluene for 48h; Reflux;
Stage #2: With potassium hexafluorophosphate In toluene
92%
With potassium hexafluorophosphate at 120 - 180℃; for 0.75h; microwave irradiation;90%
1-Butylimidazole
4316-42-1

1-Butylimidazole

dimethyl sulfate
77-78-1

dimethyl sulfate

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; dimethyl sulfate for 0.25h;
Stage #2: With sodium hexaflorophosphate In water
92%
1-butyl-3-methylimidazolium chloride

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate In acetone for 24h;90%
methanol
67-56-1

methanol

N-methyl-N'-n-butylimidazolium-2-carboxylate
671779-18-3

N-methyl-N'-n-butylimidazolium-2-carboxylate

A

potassium monomethylcarbonate
14660-45-8

potassium monomethylcarbonate

B

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate at 20℃; for 12h;A 87%
B 72%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

1-iodo-butane
542-69-8

1-iodo-butane

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With potassium hexafluorophosphate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 10h;85%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;75%
potassium fluoride

potassium fluoride

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

N-trimethylsilyl-tris(pentafluorethyl)phosphazen

Trimethyl borate
121-43-7

Trimethyl borate

hydrogen fluoride
7664-39-3

hydrogen fluoride

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

A

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

1-methyl-3-n-butylimidazolium pentafluoroethyltrifluoroborate

B

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

1-methyl-3-butylimidazolium (pentafluoroethyl)pentafluorophosphate

C

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

1-methyl-3-butylimidazolium bis(pentafluoroethyl)tetrafluorophosphate

D

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: potassium fluoride; N-trimethylsilyl-tris(pentafluorethyl)phosphazen; Trimethyl borate In 1,2-dimethoxyethane at 20 - 60℃; for 1h;
Stage #2: hydrogen fluoride In 1,2-dimethoxyethane; water at 0 - 20℃; for 3h;
Stage #3: 1-butyl-3-methylimidazolium chloride In water
A 60%
B 30%
C 6%
D 4%
1-Butylimidazole
4316-42-1

1-Butylimidazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 1-Butylimidazole; carbonic acid dimethyl ester In methanol at 135℃; for 7h;
Stage #2: With sodium hexaflorophosphate In methanol; acetone at 25℃; for 2h;
52%
1-Butylimidazole
4316-42-1

1-Butylimidazole

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 - 70 °C
2: NH4PF6
View Scheme
hexafluorophosphate anion

hexafluorophosphate anion

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
at 20℃;
formaldehyd
50-00-0

formaldehyd

Glyoxal
131543-46-9

Glyoxal

N-butylamine
109-73-9

N-butylamine

methylamine
74-89-5

methylamine

A

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

B

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

1,3-dimethyl-1H-imidazol-3-ium hexafluorophosphate

C

1,3-di-n-butylimidazolium hexafluorophosphate

1,3-di-n-butylimidazolium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: formaldehyd; N-butylamine; methylamine In water at 0℃;
Stage #2: With hexafluorophosphoric acid In water at 0℃;
Stage #3: Glyoxal In water at 0 - 20℃;
1-butyl-3-methylimidazolium halide

1-butyl-3-methylimidazolium halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With sodium hexaflorophosphate
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

n-butyl halide

n-butyl halide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
With alkali metal hexafluorophosphate at 150℃; for 0.5h; Microwave irradiation; Cooling; neat (no solvent);
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water at 20℃; for 24h;
sodium hexaflorophosphate

sodium hexaflorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

Conditions
ConditionsYield
In water
Ionic liquid; Inert atmosphere;
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

Conditions
ConditionsYield
With Amberlyst A-26 (Cl- form) In methanol100%
3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine
30169-25-6

3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

6-(1-butyl-3-methyl-1,3-dihydroimidazol-2-ylidene)-6H-[1,2,4,5]tetrazin-3-one

6-(1-butyl-3-methyl-1,3-dihydroimidazol-2-ylidene)-6H-[1,2,4,5]tetrazin-3-one

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With potassium carbonate In acetonitrile for 0.666667h; Heating;
Stage #2: 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine In acetonitrile Heating; Further stages.;
99%
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methyl-1H-imidazole-2(3H)-thione
119393-94-1

1-butyl-3-methyl-1H-imidazole-2(3H)-thione

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; Electrolysis; Inert atmosphere;
Stage #2: With sulfur for 0.166667h; Inert atmosphere; Irradiation;
99%
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methyl-2-imidazolone
586965-19-7

1-butyl-3-methyl-2-imidazolone

Conditions
ConditionsYield
With superoxide radical anion at 25℃; under 742.574 Torr; Kinetics; Inert atmosphere;95%
AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

[Au(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(BMIM)][PF6]

[Au(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(BMIM)][PF6]

Conditions
ConditionsYield
In toluene byproducts: H2O; Au complex and (C3H3N2(CH3)C4H9)PF6 added to toluene, stirred at 25°C for 14 h; pptd. (pentane), collected on a frit, washed (pentane), dried (vac.); elem. anal.;95%
chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-2-(diphenylphosphanyl)-3-methylimidazolium hexafluorophosphate

1-butyl-2-(diphenylphosphanyl)-3-methylimidazolium hexafluorophosphate

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.75h; Metallation;
Stage #2: chloro-diphenylphosphine In tetrahydrofuran; hexane at -78℃; for 0.166667h; Substitution;
89%
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With n-butyllithium In hexane; dichloromethane at -78℃; for 1h;
Stage #2: chloro-diphenylphosphine In hexane; dichloromethane at -78 - 20℃;
88%
With n-butyllithium In hexane; dichloromethane at -78℃; for 1.08333h;84%
europium(III) chloride hexahydrate

europium(III) chloride hexahydrate

4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione
893-33-4

4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-butyl-3-methylimidazolium tetrakis(naphthoyltrifluoroacetonato)europate(III)

1-butyl-3-methylimidazolium tetrakis(naphthoyltrifluoroacetonato)europate(III)

Conditions
ConditionsYield
With NaOH In ethanol; water (N2) soln. 1M NaOH was added to soln. ligand in EtOH at room temp., EuCl3*6H2O was added, stirred for 4 h at 50°C, evapd., residue was washed with hexane, dissolved in water, soln. (C4mim)Br in aq. EtOH was added, stirred for 1 h at room temp.; ppt. was filtered, washed with hexane, dried under vac.; elem. anal.;77%
carbon disulfide
75-15-0

carbon disulfide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-n-butyl-3-methylimidazolium-2-carbodithioate

1-n-butyl-3-methylimidazolium-2-carbodithioate

Conditions
ConditionsYield
Stage #1: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: carbon disulfide In tetrahydrofuran at 20℃; for 0.5h; Mechanism; Inert atmosphere;
76%
terbium(III) nitrate pentahydrate

terbium(III) nitrate pentahydrate

acetylacetone
123-54-6

acetylacetone

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

[1-butyl-3-methylimidazolium ][Tb(acetylacetonate)4]

[1-butyl-3-methylimidazolium ][Tb(acetylacetonate)4]

Conditions
ConditionsYield
Stage #1: acetylacetone With sodium hydroxide In ethanol; water pH=8;
Stage #2: 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In ethanol; water at 50℃; for 0.5h;
Stage #3: terbium(III) nitrate pentahydrate In ethanol; water at 50℃; for 2h;
72%
carbon dioxide
124-38-9

carbon dioxide

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

N-methyl-N'-n-butylimidazolium-2-carboxylate
671779-18-3

N-methyl-N'-n-butylimidazolium-2-carboxylate

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 100℃; under 60006 Torr; for 12h; Autoclave;70%
C4H4CuN4(1+)*F6P(1-)

C4H4CuN4(1+)*F6P(1-)

[BMIm]3[Nb6Cl12(NCS)6]

[BMIm]3[Nb6Cl12(NCS)6]

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

[BMIm][Nb6Cl12(SCN)6{Cu(CH3CN)}2]

[BMIm][Nb6Cl12(SCN)6{Cu(CH3CN)}2]

Conditions
ConditionsYield
In acetonitrile Inert atmosphere; Glovebox; Schlenk technique;41%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

iron pentacarbonyl
13463-40-6, 71564-23-3

iron pentacarbonyl

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

hexakis(1-methylimidazole)iron(II) hexafluorophosphate

hexakis(1-methylimidazole)iron(II) hexafluorophosphate

Conditions
ConditionsYield
In further solvent(s) byproducts: CO; Sonication; Fe complex and ligand dispersed in ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate, conicated at 40-50°C for 30 min (air); pptd.(ethanol), elem. anal., XRD;28%
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

1-n-butyl-3-methyl-2,3-dihydro-imidazol-2-ylidene
366491-14-7

1-n-butyl-3-methyl-2,3-dihydro-imidazol-2-ylidene

Conditions
ConditionsYield
With n-butyllithium In hexane; dichloromethane at -78℃; for 1h;
With N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide at 25℃; Inert atmosphere; Electrolysis;
In N,N-dimethyl-formamide at 25℃; Inert atmosphere; Electrolysis;
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

A

1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

B

1-butylene
106-98-9

1-butylene

C

1-fluorobutane
2366-52-1

1-fluorobutane

Conditions
ConditionsYield
With cesium fluoride at 150℃; for 96h;
furfural
98-01-1

furfural

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

A

methyl 2-(furan-2-yl(hydroxy)methyl)acrylate
87102-10-1

methyl 2-(furan-2-yl(hydroxy)methyl)acrylate

B

C13H19N2O2(1+)*F6P(1-)

C13H19N2O2(1+)*F6P(1-)

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 24h; Baylis-Hillman;
3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate
174501-64-5

3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate

A

3-butyl-2-fluoro-1-methyl-3H-imidazol-1-ium

3-butyl-2-fluoro-1-methyl-3H-imidazol-1-ium

B

3-[4-(1-butyl-3-methyl-2,3-dihydro-1H-imidazol-2-yl)-butyl]-1-methyl-3H-imidazol-1-ium

3-[4-(1-butyl-3-methyl-2,3-dihydro-1H-imidazol-2-yl)-butyl]-1-methyl-3H-imidazol-1-ium

C

1-methyl-3H-imidazolium

1-methyl-3H-imidazolium

Conditions
ConditionsYield
In water; acetonitrile Radiolysis;

174501-64-5Relevant academic research and scientific papers

High performance asymmetric supercapacitor based on MnO2 electrode in ionic liquid electrolyte

Zhang, Xuan,Zhao, Dandan,Zhao, Yongqing,Tang, Pengyi,Shen, Yinglin,Xu, Cailing,Li, Hulin,Xiao, Yu

, p. 3706 - 3712 (2013)

In this work, the electrochemical properties of a MnO2 nanocomposite electrode were investigated in 1-butyl-3-methyl-imidazolium hexafluorophosphate ([Bmim]PF6)/N,N-dimethylformamide (DMF) electrolyte. The [Bmim]PF6/DMF electrolyte with different volume fractions exhibits significant influence on the electrochemical properties of the electrode. When the volume ratio of [Bmim]PF6 and DMF was 1:1, the electrode showed the best electrochemical performance. The operation potential window of the MnO2 nanocomposite electrode in ionic liquids was 2.1 V and the specific capacitance according to the mass of MnO2 was 523.3 F g-1 at 3 A g-1. Then, a high-voltage (3 V) MnO2 asymmetric supercapacitor was successfully fabricated, using the MnO2 nanocomposite electrode, activated carbon and [Bmim]PF 6/DMF as the positive electrode, negative electrode and electrolyte, respectively. The MnO2 asymmetric supercapacitor displayed a maximum specific energy of 67.5 W h kg-1 at a specific power of 593.8 W kg-1 and a maximum specific power of 20.4 kW kg-1 at a specific energy of 8.5 W h kg-1. The impressive results showed that [Bmim]PF6/DMF could be a promising electrolyte for MnO2 supercapacitors.

Examination of ionic liquids and their interaction with molecules, when used as stationary phases in gas chromatography

Armstrong, Daniel W.,He, Lingfeng,Liu, Yan-Song

, p. 3873 - 3876 (1999)

Stable room-temperature ionic liquids (RTILs) have been used as novel reaction solvents. They can solubilize complex polar molecules such as cyclodextrins and glycopeptides. Their wetting ability and viscosity allow them to be coated onto fused silica capillaries. Thus, 1-butyl-3- methylimidazolium hexafluorophosphate and the analogous chloride salt can be used as stationary phases for gas chromatography (GC). Using inverse GC, one can examine the nature of these ionic liquids via their interactions with a variety of compounds. The Rohrschneider-McReynolds constants were determined for both ionic liquids and a popular commercial polysiloxane stationary phase. Ionic liquid stationary phases seem to have a dual nature. They appear to act as a low-polarity stationary phase to nonpolar compounds. However, molecules with strong proton donor groups, in particular, are tenaciously retained. The nature of the anion can have a significant effect on both the solubilizing ability and the selectivity of ionic liquid stationary phases. It appears that the unusual properties of ionic liquids could make them beneficial in many areas of separation science.

One-pot and solventless synthesis of ionic liquids under ultrasonic irradiation

Estager, Julien,Lévêque, Jean-Marc,Cravotto, Giancarlo,Boffa, Luisa,Bonrath, Werner,Draye, Micheline

, p. 2065 - 2068 (2007)

A novel method is described for the one-pot synthesis of various ionic liquids in a competitive time. By using ultrasonic irradiation, different families of nitrogen-bearing ionic liquids can be obtained in a solvent-free or in aqueous medium, which gives a greener touch to the overall process. Georg Thieme Verlag Stuttgart.

Association of ionic liquids in solution: Conductivity studies of [BMIM][Cl] and [BMIM][PF6] in binary mixtures of acetonitrile + methanol: Ion association in ionic liquid solutions

Jan, Roohi,Rather, Ghulam Mohammad,Bhat, Mohsin Ahmad

, p. 738 - 745 (2013)

The concentration dependence of molar conductance for 1-butyl-3- methylimidazolium chloride and 1-butyl-3-methylimidazolium hexafluorophosphate in binary mixtures of acetonitrile + methanol was investigated to explore the ion association behavior of imidazolium based ionic liquids. The limiting molar conductance (Λm0), association constants (K a 0) and the maximal distance between the oppositely charged ions in ion pairs (R ij ) in the mixed solvent mixtures were evaluated following the framework of Barthel's low-concentration chemical model. The investigated ILs display opposing trends in ion association behavior with change in solvent composition of acetonitrile + methanol binary mixtures. The results are discussed in light of ionic liquid and solvent specific ion-solvent and ion-ion interactions in the mixed solvent systems.

Effect of temperature on the purity of product in the preparation of 1-butyl-3-methylimidazolium-based ionic liquids

K?rkk?inen, Johanna,Asikkala, Janne,Laitinen, Risto S.,Lajunen, Marja K.

, p. 763 - 770 (2004)

The preparation of room-temperature ionic liquids 1-butyl-3- methylimidazolium chloride, hexafluorophosphate, and dicyanamide by microwave-assisted reaction in non-solvent and solvent conditions has been studied in this contribution. A special emphasis is put on the effect of the reaction temperature on the purity of ionic liquids that was monitored by electrospray ionisation mass spectrometry and 1H NMR. The X-ray structure of 1-butyl-3-methylimidazolium chloride is presented.

Liquid-liquid equilibria of room-temperature ionic liquids and butan-1-ol

Wu,Marsh, Kenneth N.,Deev, Alexander V.,Boxall, John A.

, p. 486 - 491 (2003)

Room-temperature ionic liquids are salts that are liquid at room temperature. Their use as catalysts and catalytic support has been studied extensively. However, there are very few measurements on their solubility and phase equilibria in common organic solvents. In this work, the liquid-liquid phase equilibria of mixtures of room-temperature ionic liquids, 1-alkyl-3-methylimidazolium hexafluorophosphate, [Rnmim][PF6] (1) where Rn = butyl, pentyl, hexyl, heptyl, and octyl, with butan-1-ol (2) over a composition range have been measured. The binodal coexistence curves of the mixtures were found to have an upper critical solution temperature (USCT) at x2 ≈ 0.9. The UCST decreases with increase in the length of the alkyl chain of the ionic liquid, with the UCST of the butyl at 373 K and that of the octyl at 326 K. Both the UCST and the composition at the UCST as a function of the 1-alkyl group chain length can be reasonably well predicted from theory on the basis of unimolecular quantum chemical calculations.

Spectroscopic and photophysical properties of ZnTPP in a room temperature ionic liquid

Szmytkowski, Jedrzej,Bond, Toby,Paige, Matthew F.,Scott, Robert W. J.,Steer, Ronald P.

, p. 11471 - 11476 (2010)

The steady-state absorption and emission spectra and the time-resolved Soret- and Q-band excited fluorescence profiles of the model metalloporphyrin, ZnTPP, have been measured in a highly purified sample of the common room temperature ionic liquid, [bmim][PF6]. S2-S0 emission resulting from Soret-band excitation behaves in a manner completely consistent with that of molecular solvents of the same polarizability. The ionic nature of the solvent and its slow solvation relaxation times have no significant effect on the nature of the radiationless decay of the S2 state, which decays quantitatively to S1 at a population decay rate that is consistent with the weak coupling case of radiationless transition theory (energy gap law). The ratio of the intensities of the Qα:Qβ (0-0:1-0) bands is consistent with the solvatochromic shift correlation data obtained for molecular solvents. The temporal S1 fluorescence decay profiles measured at a single emission wavelength are biexponential; the longer-lived major component is similar to that observed for ZnTPP in molecular solvents, and the minor shorter-lived component is attributed to solvent relaxation processes on a nanosecond time scale.

A rationalization of the solvent effect on the Diels-Alder reaction in ionic liquids using multiparameter linear solvation energy relationships

Bini, Riccardo,Chiappe, Cinzia,Mestre, Veronica Llopsis,Pomelli, Christian Silvio,Welton, Thomas

, p. 2522 - 2529 (2008)

The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) having different hydrogen bond acceptor abilities has been carried out in several ionic liquids and molecular solvents in order to obtain information about the factors affecting reactivity and selectivity. The solvent effects on these reactions are examined using multiparameter linear solvation energy relationships. The collected data provide evidence that the solvent effects are a function of both the solvent and the solute. For a solvent effect to be seen, the solute must have a complimentary character; selectivities and rates are determined by the solvent hydrogen bond donation ability (α) in the reactions of acrolein and methyl acrylate, but not of acrylonitrile. The Royal Society of Chemistry 2008.

Preparation of second generation ionic liquids by efficient solvent-free alkylation of N-heterocycles with chloroalkanes

Cravotto, Giancarlo,Gaudino, Emanuela Calcio,Boffa, Luisa,Leveque, Jean-Marc,Estager, Julien,Bonrath, Werner

, p. 149 - 156 (2008)

Non-conventional techniques, such as microwave (MW) and power ultrasound (US) as well as combined MW/US irradiation, have been used to promote one-pot synthesis of second-generation ionic liquids (ILs), cutting down reaction times and improving yields. However, the use of chloroalkanes in the alkylation of N-heterocycles requires more drastic conditions if results are to match those obtained with more reactive alkyl halides. The present paper describes a series of MW- or MW/US-promoted IL preparations starting from chloroalkanes and classic heterocycles (1-methylimidazole, pyridine and 1-methylpyrrolidine). When reactions were carried out under conventional heating in an oil bath they required longer reaction times and gave poorer yields. 1H-NMR analysis and ion-exchange chromatography showed that the present solventless procedure afforded ILs of satisfactory purity. The observed high yields (usually 70-98% isolated), and short reaction times showed that a straightforward access to ILs can be also achieved with the use of alkyl chlorides, resulting in a considerable reduction of costs.

Effect of ionic liquids on the conformation of a porphyrin-based viscometer

Jameson, Laramie P.,Kimball, Joseph D.,Gryczynski, Zygmunt,Balaz, Milan,Dzyuba, Sergei V.

, p. 18300 - 18304 (2013)

Structure of the cationic and anionic counterparts of ionic liquids has a significant impact on the conformational bias of the porphyrin rotor; an apparent correlation between the conformation and the viscosity of ionic liquids was noted, albeit it was found to be distinct and more complex from that found in molecular solvents.

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