65039-09-0

Basic information

• Product Name: 1-Ethyl-3-methylimidazolium chloride
• Synonyms: 1-ethyl-3-methyl-1h-imidazoliumchloride;EMIM CL;BASIONIC(TM) ST 80;1-ETHYL-3-METHYLIMIDAZOLIUM CHLORIDE;1-Ethyl-3-methyl-1H-imidzaolium chloride;1-ETHYL-3-METHYLIMIDAZOLIUMCHLORIDE[FORMOLTENSALT];1-Ethyl-3-methylimidazolium chloride, 99+%;BASIONIC(R) ST 80
• CAS NO: 65039-09-0
• Molecular Formula: C₆H₁₁N₂*Cl
• Molecular Weight: 146.62
• EINECS: 1806241-263-5
• Product Categories: Imidazolium Compounds;Imidazolium Salts (Ionic Liquids);Ionic Liquids;Synthetic Organic Chemistry;Ionic Liquids;Chemical Synthesis;Imidazolium;Chemical Synthesis;Specialty Synthesis;Pyridines ,Halogenated Heterocycles
• Mol File: 65039-09-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 77-79 °C(lit.)
• Flash Point: 186 °C
• Appearance: Pale yellow/Agglomerating Crystalline Powder
• Density: 1.435 g/cm3
• Vapor Pressure: 0Pa at 20-50℃
• Storage Temp.: Store below +30°C.
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• Stability: Stable. Very hygroscopic. Incompatible with strong oxidizing agents.
• BRN: 5163190
• CAS DataBase Reference: 1-Ethyl-3-methylimidazolium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-3-methylimidazolium chloride(65039-09-0)
• EPA Substance Registry System: 1-Ethyl-3-methylimidazolium chloride(65039-09-0)

Safety Data

• Hazard Codes: Xi,N,T
• Statements: 36/38-51/53-36/37/38-25
• Safety Statements: 26-57-45-37/39-29
• RIDADR: 2811
• WGK Germany: 2
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 65039-09-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 65039-09-0 differently. You can refer to the following data:
1. Used in cellulose processing.
2. 1-Ethyl-3-methylimidazolium chloride is an imidazolium chloride ionic liquid that can be used as:A starting material for the preparation of 1-ethyl-3-methylimidazolium chloride/tetrafluoroborate (EMI.Cl.BF4) molten salt for electrochemical studies.A solvent as well as catalyst for the depolymerization of oak wood lignin.A solvent in the hydrolysis of hemicellulose (xylan) to xylose using Br?nsted acid catalysts.

Definition

ChEBI: An organic chloride salt in which the cationic component is 1-ethyl-3-methylimidazolium.

General Description

1-Ethyl-3-methylimidazolium chloride is an organic salt and a room-temperature ionic liquid (RTIL). It is used as a solvent in many organic reactions due to its unique properties like small vapor pressures, high thermal stabilities and ionic conductivities.

InChI:InChI=1/C6H11N2.ClH/c1-3-8-5-4-7(2)6-8;/h4-6H,3H2,1-2H3;1H/q+1;/p-1

Synthetic route

1-methyl-1H-imidazole (616-47-7) + chloroethane (75-00-3) → 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
In ethanol at 35℃; for 10h; Wavelength; UV-irradiation;	100%
	79%
In acetonitrile at 70℃; for 168h;	71%

benzyl chloride (100-44-7) + 1-ethyl-3-methylimidazolium acetate (143314-17-4) → Benzyl acetate (140-11-4) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 20℃; for 2h; Inert atmosphere;	A 95% B n/a

1-ethyl-3-methylimidazolium acetate (143314-17-4) + 1,2-dichloro-ethane (107-06-2) → ethylene glycol diacetate (111-55-7) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 70℃; for 3h; Inert atmosphere;	A 90% B n/a

methyl (2R)-2-chloropropanoate (77287-29-7) + 1-ethyl-3-methylimidazolium acetate (143314-17-4) → (R)-O-Acetyllactic acid Methyl Ester (60426-97-3) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 20℃; for 2h; Inert atmosphere;	A 90% B n/a

dichloromethane (75-09-2) + 1-ethyl-3-methylimidazolium acetate (143314-17-4) → diacetoxymethane (628-51-3) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 50℃; for 16h; Inert atmosphere;	A 86% B n/a

s-butyl chloride (78-86-4, 53178-20-4) + 1-ethyl-3-methylimidazolium acetate (143314-17-4) → sec-Butyl acetate (105-46-4) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 80℃; for 16h; Inert atmosphere;	A 82% B n/a

N-Ethylimidazole (7098-07-9) + carbonic acid dimethyl ester (616-38-6) → 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
Stage #1: N-Ethylimidazole With hydrogenchloride In water Cooling with ice; Stage #2: carbonic acid dimethyl ester at 169.84℃; for 8h; Autoclave; Neat (no solvent);

1-methylimidazolium chloride (35487-17-3) + Diethyl carbonate (105-58-8) → 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 169.84℃; for 8h; Autoclave; Neat (no solvent);	41.6 %Spectr.

1-ethyl-3-methylimidazolium 4-chlorobutylsulfonate: → 1,4-butane sultone (1633-83-6) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 100℃; Vacuum;

sodium 2,2,2-trifluoroacetate (2923-18-4) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0) → 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate

Conditions	Yield
In diethyl ether; acetonitrile for 1h;	100%
In diethyl ether; acetone; acetonitrile at 20℃; for 2h;

1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0) → 1-ethyl-3-methylimidazolium fluorosulfonate

Conditions	Yield
With potassium fluorosulfonate In diethyl ether; acetonitrile for 1h;	100%
With fluorosulphonic acid at 0 - 60℃; Inert atmosphere;	57%

1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0) → 1-ethyl-3-methylimidazolium tetrafluoroborate (143314-16-3)

Conditions	Yield
With tetrafluoroboric acid In water at 20℃;	100%
With sodium tetrafluoroborate at 79.84℃; for 10h; Glovebox; Inert atmosphere;
With sodium tetrafluoroborate In acetone at 20℃; for 24h;

trimethylsilyl trifluoroacetate (400-53-3) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0) → 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate

Conditions	Yield
Stage #1: trimethylsilyl trifluoroacetate; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride for 3h; Heating / reflux; Stage #2: With chloro-trimethyl-silane	100%

diethyl sulphite (623-81-4) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0) → 1-ethyl-3-methylimidazolium ethylsulfite (919788-70-8)

Conditions	Yield
at 60℃; under 750.075 - 1125.11 Torr; for 60h;	100%

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 75-00-3 chloroethane 
• 7098-07-9 N-Ethylimidazole 
• 616-38-6 carbonic acid dimethyl ester 
• 35487-17-3 1-methylimidazolium chloride 
• 105-58-8 Diethyl carbonate 
• 77287-29-7 methyl (2R)-2-chloropropanoate 
• 143314-17-4 1-ethyl-3-methylimidazolium acetate 
• 78-86-4 s-butyl chloride 
• 107-06-2 1,2-dichloro-ethane 
• 100-44-7 benzyl chloride 
• 75-09-2 dichloromethane 

Downstream Products

• 143314-16-3 1-ethyl-3-methylimidazolium tetrafluoroborate 
• 174899-65-1 3-ethyl-1-methyl-1H-imidazol-3-ium 2,2,2-trifluoroacetate 
• 44142-34-9 [VO₂Cl₂]^(1-) 
• 7727-18-6 vanadium(V) oxychloride 
• 48000-49-3 CH₃CH₂AlCl₃^(1-) 
• 951021-14-0 1-ethyl-3-methylimidazolium phenyltrifluoroboronate 
• 145022-45-3 1-ethyl-3-methyl imadazolium methanesulfonate 
• 143314-17-4 1-ethyl-3-methylimidazolium acetate 
• 616-47-7 1-methyl-1H-imidazole 
• 7098-07-9 N-Ethylimidazole 
• 947601-94-7 1-ethyl-3-methyl-1H-imidazol-3-ium hydrogencarbonate 
• 7681-52-9 sodium hypochlorite 
• 64-18-6 formic acid 
• 141-82-2 malonic acid 

Relevant articles and documents

Syntheses and physicochemical properties of new ionic liquids based on the hexafluorouranate anion

The first syntheses of a series of ionic liquids based on the hexafluorouranate(V) anion are described along with their physicochemical and electrochemical properties. The green roomtemperature ionic liquid, 1-ethyl-3-methylimidazolium hexafluorouranate (EMImUF6), exhibits a conductivity of 7.9 mS cm-1, viscosity of 59 cP, and electrochemical window of 2.3 V at 298 K. Copyright

Preparation of nanocellulose using ionic liquids: 1-propyl-3-methylimidazolium chloride and 1-ethyl-3-methylimidazolium chloride

Cellulose nanocrystals were prepared using ionic liquids (ILs), 1-ethyl-3-methylimidazolium chloride [EMIM][Cl] and 1-propyl-3-methylimidazolium chloride [PMIM][Cl], from microcrystalline cellulose. The resultant samples were characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), dynamic light scattering (DLS), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The XRD results showed that nanocellulose obtained by treatment with both ILs preserved basic cellulose I structure, but crystallinity index of samples (except for Sigmacell treated with [EMIM][Cl]) was lower in comparison to the starting microcrystalline cellulose. The DLS results indicated noticeably smaller particle sizes of prepared cellulose for material treated with [PMIM][Cl] compared to cellulose samples hydrolyzed with [EMIM][Cl], which were prone to agglomeration. The obtained nanocellulose had a rod-like structure that was confirmed by electron microscopy analyses. Moreover, the results described in this paper indicate that cation type of ILs influences particle size and morphology of cellulose after treatment with ionic liquids.

Ionic Liquids Catalyzed Friedel–Crafts Alkylation of Substituted Benzenes with CCl4 Toward Trichloromethylarenes

Abstract: An ionic liquid catalyzed Friedel–Crafts alkylation reaction of substituted benzenes with CCl4 was developed. The reaction proceeded efficiently under mild conditions, gave corresponding trichloromethylarenes with diversity functional groups in moderate to good yields. The influence of Lewis acidity of ionic liquids on the conversion of the alkylation reaction has been investigated. Notably, the probable mechanism of this reaction has been proposed with the assistance of 27Al NMR spectroscopy. It was noteworthy that the predominance of [Al2Cl7]? species in EmimCl–AlCl3, N = 0.67 could be detected by 27Al NMR spectral analysis, and [AlCl4]? was generated at the beginning of reaction. Additionally, it was found that [AlCl4]? could be transformed into [Al2Cl7]? when the reaction finished. Some control experiments confirmed that the interaction between Lewis acidic species [Al2Cl7]? of the ionic liquid and CCl4 led to the change in speciation of aluminum during the alkylation reactions. Graphical Abstract: [Figure not available: see fulltext.].

Combination effect of ionic liquid components on the structure and properties in 1,4-benzenedicarboxylate based zinc metal-organic frameworks

Two types of 2D [RMI]2[Zn3(BDC)3X2] (Type A) and 3D [Zn(BDC)(H2O)] (Type B) (H2BDC = 1,4-benzenedicarboxylate acid) compounds were synthesized with three kinds of 1-alkyl-3-methyl imidazolium halide ([RMI]X) ionic liquids. Type A is the primary structure model showing a (3,6) network. Type B can be obtained from [BMI]Cl, [AMI]Cl and [AMI]Br media, showing a 4,4-connected {42·84} network. The structure, TG, and fluorescence analyses demonstrate the combination effect of the RMI+ templating effect and X- controlling the structure types. The boundary between Types A and B is from [PMI]Cl, via [BMI]Br, to [AMI]I as the reaction media. The decomposition temperatures of the compounds in Type A decrease with increased RMI+, while X- anions exert the influence that compounds containing Br- supply the highest thermal stability. Similarly, with increased RMI+, or X = I-, the compounds show red shifts compared to the emissions of the ligand.