107937-17-7

Basic information

• Product Name: 1-Propyl-2,3-diMethyliMidazoliuM broMide
• Synonyms: 1-Propyl-2,3-diMethyliMidazoliuM broMide;PDMIMBr;1,2-dimethyl-3-propylimidazolium bromide
• CAS NO: 107937-17-7
• Molecular Formula: Br*C₈H₁₅N₂
• Molecular Weight: 219.1221
• Mol File: 107937-17-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Propyl-2,3-diMethyliMidazoliuM broMide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propyl-2,3-diMethyliMidazoliuM broMide(107937-17-7)
• EPA Substance Registry System: 1-Propyl-2,3-diMethyliMidazoliuM broMide(107937-17-7)

Safety Data

• Hazardous Substances Data: 107937-17-7(Hazardous Substances Data)

Usage

General Description

1-Propyl-2,3-dimethylimidazolium bromide is a chemical compound that serves as an efficient and versatile reagent in various chemical reactions due to its unique physical and chemical properties. Often used as an ionic liquid, this substance has attracted attention in the field of green chemistry. The structure of 1-Propyl-2,3-dimethylimidazolium bromide consists of a 1-propyl-2,3-dimethylimidazolium cation and a bromide anion. It is a white to off-white crystalline powder at room temperature and is soluble in water, alcohol, and some organic solvents. Taking precautions is required while handling this compound as it can cause skin and eye irritation, and specific measures should be taken in case of accidental ingestion or inhalation.

Synthetic route

1,2-dimethyl-1H-imidazole (1739-84-0) + propyl bromide (106-94-5) → 1,2-dimethyl-3-propylimidazolium bromide (107937-17-7)

Conditions	Yield
In cyclohexane at 20℃;
In toluene
In acetonitrile at 80℃; for 2h;
Inert atmosphere;
In acetonitrile for 16h;

tris(bicyclo[2.2.1]heptene)platinum(0) + (1,3-dimesitylimidazol-2-ylidene)platinum(0) bis(η2-dimethylfumarate) + 1,2-dimethyl-3-propylimidazolium bromide (107937-17-7) → (platinum)(hydride)(bromide)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(1,2-dimethyl-3-propylimidazole) + (platinum)(hydride)(bromide)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(1,2-dimethyl-3-propylimidazole)

Conditions	Yield
In acetone 55°C;

tris(bicyclo[2.2.1]heptene)platinum(0) + 1,2-dimethyl-3-propylimidazolium bromide (107937-17-7) + (platinum)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(η2-styrene)2 → (platinum)(hydride)(bromide)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(1,2-dimethyl-3-propylimidazole) + (platinum)(hydride)(bromide)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(1,2-dimethyl-3-propylimidazole)

Conditions	Yield
In acetone 55°C;

tris(bicyclo[2.2.1]heptene)platinum(0) + 1,2-dimethyl-3-propylimidazolium bromide (107937-17-7) + [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene (141556-42-5) → (platinum)(hydride)(bromide)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(1,2-dimethyl-3-propylimidazole) + (platinum)(hydride)(bromide)(1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)(1,2-dimethyl-3-propylimidazole)

Conditions	Yield
In acetone 55°C, 1 h;

1,2-dimethyl-3-propylimidazolium bromide (107937-17-7) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → 1,2-dimethyl, 3-propyl imidazolium bis(trifluoromethanesulfonyl)imide (169051-76-7)

Conditions	Yield
In water at 20℃;
In water
In water at 20℃; for 3h;	34.8 g

1,2-dimethyl-3-propylimidazolium bromide (107937-17-7) → 1,2-dimethyl-3-propylimidazolium tetrafluoroborate (157310-72-0)

Conditions	Yield
With sodium tetrafluoroborate In water

1,2-dimethyl-3-propylimidazolium bromide (107937-17-7) → C8H15N2(1+)*HO4S(1-)

Conditions	Yield
With sodium hydrogen sulfate Inert atmosphere;

1,2-dimethyl-3-propylimidazolium bromide (107937-17-7) → 1,2-dimethyl-3-propylimidazolium hydroxide

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 4h;

Upstream product

• 1739-84-0 1,2-dimethyl-1H-imidazole 
• 106-94-5 propyl bromide 

Downstream Products

• 169051-76-7 1,2-dimethyl-3-propylimidazolium bis(trifluoromethylsulfonyl)imide 
• 157310-72-0 1,2-dimethyl-3-propylimidazolium tetrafluoroborate 

Relevant articles and documents

Ionic liquids promote PCR amplification of DNA

A bicyclic imidazolium ionic liquid (4d), [b-4C-im][Br], was found to be highly effective not only for promoting PCR of GC-rich DNA by minimizing non-specific amplification, but also for facilitating PCR of normal-GC DNA under mild conditions.

Estimation and structural effect on physicochemical properties of alkylimidazolium-based ionic liquids with different anions

Ten kinds of alkylimidazolium-based aprotic ionic liquids (AILs) with hydrogen carbonate, dihydrogen phosphate, and hydrogen sulfate anions were prepared, and methods of elemental analysis, infrared spectroscopy, and proton nuclear magnetic resonance were employed to characterize the ILs, respectively. Properties such as electrical conductivity, density, dynamic viscosity, surface tension, were measured and correlated with thermodynamic and empirical equations over various temperature ranges under ambient conditions. Some significant thermodynamic parameters of the ILs were estimated. The trends of changing with temperature for the dynamic viscosity and the electrical conductivity were described by the Vogel-Fulcher-Tamman equation. The activation energies of dynamic viscosity and electrical conductivity were also calculated. Further, the structures and the energetics of the ILs ions were obtained through combining density functional theory calculations and the COSMO-RS methodology. The structural effects of ion variation on the properties of the ILs were studied.

Physicochemical properties of imidazolium-derived ionic liquids with different C-2 substitutions

Five room temperature ionic liquids based on C-2 substituted imidazolium cations and bis(trifluoromethanesulfonyl)imide (TFSI) anions were synthesized and their physicochemical properties: thermal property, density, viscosity, ionic conductivity, self-diffusion coefficients, and electrochemical stability, were systematically investigated. The temperature dependence of both viscosity and ionic conductivities of these ionic liquids can be described by the Vogel-Fulcher-Tamman (VFT) equation. Compared with the reference, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, the introduction of functional groups at the C-2 position generally increased the viscosity and lowered the ionic conductivity. The introduction of an ether group (-CH2OCH2CH2CH2CH3) at the C-2 position not only enhanced the reduction stability of the ionic liquids but also exhibited the lowest solid electrolyte interfacial resistance (R SEI). In contrast, the introduction of a cyano group (-CN) at the C-2 position not only decreased the reduction stability but also adversely increased the SEI resistance. The effect of the C-2 substitution on the reduction stability was explained by the change in the energy level of the lowest unoccupied molecular orbital. The self-diffusion coefficients (D) of each ion were measured by pulsed field gradient nuclear magnetic resonance (PFG-NMR). The lithium transference number (tLi) of 0.5 M LiTFSI/IL solutions calculated from the self-diffusion coefficients was in the range of 0.04 to 0.09.