58175-55-6

Basic information

• Product Name: 1-hexadecyl-IMidazole
• Synonyms: 1-hexadecyl-IMidazole;1-Hexadecyl-1H-imidazole
• CAS NO: 58175-55-6
• Molecular Formula: C₁₉H₃₆N₂
• Molecular Weight: 292.50254
• Mol File: 58175-55-6.mol
• Article Data: 32

Chemical Properties

• Melting Point: 38 °C
• Boiling Point: 421.3±14.0 °C(Predicted)
• Appearance: /
• Density: 0.90±0.1 g/cm3(Predicted)
• PKA: 7.08±0.10(Predicted)
• CAS DataBase Reference: 1-hexadecyl-IMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-hexadecyl-IMidazole(58175-55-6)
• EPA Substance Registry System: 1-hexadecyl-IMidazole(58175-55-6)

Safety Data

• Hazardous Substances Data: 58175-55-6(Hazardous Substances Data)

Usage

General Description

1-hexadecyl-IMidazole is a chemical compound known for its wide range of applications, particularly as a surfactant due to its hydrophobicity, and in the field of electrochemistry. It is largely used in the creation of vesicles and micelles, scientific processes that aid in the transportation of other molecules, often in the field of pharmacology. In chemical structure, 1-hexadecyl-IMidazole is characterized by a long hydrocarbon chain and an imidazole ring. Its longer hydrocarbon chain often contributes to the compound's hydrophobic properties. This chemical compound can be created through several synthetic methods, including a one-step hydrotermal process. Its storage should be in a tightly closed container to avoid its direct contact with air or moisture. Its mishandling can cause skin and eye irritation, therefore it should be handled carefully with proper safety measures.

Upstream product

• 288-32-4 1H-imidazole 
• 4860-03-1 1-Chlorohexadecan 
• 112-82-3 hexadecanyl bromide 
• 927690-67-3 C₂₂H₄₀N₃⁽¹⁺⁾*Br^(1-) 
• 5587-42-8 imidazolyl sodium 

Downstream Products

• 1224595-52-1 1-hexadecyl-3-phenylmethyl-1H-imidazolium bromide 
• 1224595-53-2 1-decyl-3-phenylmethyl-1H-imidazolium bromide 
• 1354971-77-9 1-hexadecyl-3-(6-hydroxyhexyl)imidazolium tosylate 

Relevant articles and documents

Small-angle neutron-scattering studies of mixed micellar structures made of dimeric surfactants having imidazolium and ammonium headgroups

Planar imidazolium cation based gemini surfactants [16-Im-n-Im-16], 2Br- (where n = 2, 3, 4, 5, 6, 8, 10, and 12), exhibit different morphologies and internal packing arrangements by adopting different supramolecular assemblies in aqueous media depending on their number of spacer methylene units (CH2)n. Detailed measurements of the small-angle neutron-scattering (SANS) cross sections from different imidazolium-based surfactant micelles in aqueous media (D2O) are reported. The SANS data, containing the information of aggregation behavior of such surfactants in the molecular level, have been analyzed on the basis of the Hayter and Penfold model for the macro ion solution to compute the interparticle structure factor S(Q) taking into account the screened Coulomb interactions between the dimeric surfactant micelles. The characteristic changes in the SANS spectra of the dimeric surfactant with n = 4 due to variation of temperature have also been investigated. These data are then compared with the SANS characterization data of the corresponding gemini micelles containing tetrahedral ammonium ion based polar headgroups. The critical micellar concentration of each surfactant micelle (cmc) has been determined using pyrene as an extrinsic fluorescence probe. The variation of cmc as a function of spacer chain length has been explained in terms of conformational variation and progressive looping of the spacer into the micellar interior upon increasing the n values. Small-angle neutron-scattering (SANS) cross sections from different mixed micelles composed of surfactants with ammonium headgroups, 16-A 0, [16-Am-n-Am-16], 2Br- (where n = 4), 16-I0, and [16-Im-n-Im-16], 2Br- (where n = 4), in aqueous media (D 2O) have also been analyzed. The aggregate composition matches with that predicted from the ideal mixing model.

N-Functionalised Imidazoles as Stabilisers for Metal Nanoparticles in Catalysis and Anion Binding

Metal nanoparticles (NPs) have physicochemical properties which are distinct from both the bulk and molecular metal species, and provide opportunities in fields such as catalysis and sensing. NPs typically require protection of their surface to impede aggregation, but these coatings can also block access to the surface which would be required to take advantage of their unusual properties. Here, we show that alkyl imidazoles can stabilise Pd, Pt, Au, and Ag NPs, and delineate the limits of their synthesis. These ligands provide an intermediate level of surface protection, for which we demonstrate proof-of-principle in catalysis and anion binding.

Molecular tunability of surface-functionalized metal nanocrystals for selective electrochemical CO2 reduction

Organic ligands are used in homogeneous catalysis to tune the metal center reactivity; in contrast, clean surfaces are usually preferred in heterogeneous catalysis. Herein, we demonstrate the potential of a molecular chemistry approach to develop efficient and selective heterogeneous catalysts in the electrochemical CO2 reduction reaction (CO2RR). We have tailor-made imidazolium ligands to promote the CO2RR at the surface of hybrid organic/inorganic electrode materials. We used silver nanocrystals for the inorganic component to obtain fundamental insights into the delicate tuning of the surface chemistry offered by these ligands. We reveal that modifying the electronic properties of the metal surface with anchor groups along with the solid/liquid interface with tail groups is crucial in obtaining selectivities (above 90% FE for CO), which are higher than the non-functionalized Ag nanocrystals. We also show that there is a unique dependency of the CO2RR selectivity on the length of the hydrocarbon tail of these ligands, offering a new way to tune the interactions between the metal surface with the electrolyte and reactants.