26576-85-2

Basic information

• Product Name: N-BUTYL-3-METHYLPYRIDINIUM BROMIDE
• Synonyms: N-BUTYL-3-METHYLPYRIDINIUM BROMIDE;1-BUTYL-3-METHYLPYRIDINIUM BROMIDE,98.0+%(LC)(T);1-Butyl-3-methylpyridinium Bromide;PyridiniuM,1-butyl-3-Methyl-, broMide (1:1);N-butyl-3-metylpyridinium bromide;[BMPy]Br;1-Butyl-3-methylpyridin-1-ium bromide
• CAS NO: 26576-85-2
• Molecular Formula: Br*C₁₀H₁₆N
• Molecular Weight: 230.14
• EINECS: 1533716-785-6
• Product Categories: Ionic Liquids;Pyridinium Compounds;Pyridinium Compounds (Ionic Liquids);Synthetic Organic Chemistry
• Mol File: 26576-85-2.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: N-BUTYL-3-METHYLPYRIDINIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BUTYL-3-METHYLPYRIDINIUM BROMIDE(26576-85-2)
• EPA Substance Registry System: N-BUTYL-3-METHYLPYRIDINIUM BROMIDE(26576-85-2)

Safety Data

• Hazardous Substances Data: 26576-85-2(Hazardous Substances Data)

Usage

General Description

N-BUTYL-3-METHYLPYRIDINIUM BROMIDE, also known as NBPB, is a chemical compound that belongs to the class of quaternary ammonium salts. It is commonly used as a phase transfer catalyst in organic synthesis and in various industrial processes. NBPB can also be used as a surfactant in electrochemical processes and as an antimicrobial agent in some applications. It is known for its ability to enhance the solubility and reactivity of certain organic compounds in aqueous and organic solvents. However, NBPB should be handled with caution as it is a potentially hazardous chemical and exposure to high concentrations of the compound can cause skin and eye irritation.

InChI:InChI=1/C10H16N.BrH/c1-3-4-7-11-8-5-6-10(2)9-11;/h5-6,8-9H,3-4,7H2,1-2H3;1H/q+1;/p-1

Upstream product

• 109-65-9 1-bromo-butane 
• 108-99-6 3-Methylpyridine 

Downstream Products

• 344790-86-9 1-butyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide 
• 712355-12-9 1-butyl-3-methylpyridinium dicyanoazanide 
• 108-99-6 3-Methylpyridine 
• 74-98-6 propane 
• 106-97-8 n-butane 

Relevant articles and documents

Synthesis of palladium nanoparticles supported on mesoporous n-doped carbon and their catalytic ability for biofuel upgrade

We report a catalyst made of Pd nanoparticles (NPs) supported on mesoporous N-doped carbon, Pd@CN0132, which was shown to be highly active in promoting biomass refining. The use of a task-specific ionic liquid (3-methyl-1-butylpyridine dicyanamide) as a precursor and silica NPs as a hard template afforded a high-nitrogen-content (12 wt %) mesoporous carbon material that showed high activity in stabilizing Pd NPs. The resulting Pd@CN 0.132 catalyst showed very high catalytic activity in hydrodeoxygenation of vanillin (a typical model compound of lignin) at low H2 pressure under mild conditions in aqueous media. Excellent catalytic results (100% conversion of vanillin and 100% selectivity for 2-methoxy-4-methylphenol) were achieved, and no loss of catalytic activity was observed after six recycles.

Ion pairing in 1-butyl-3-methylpyridinium halide ionic liquids studied using NMR and DFT calculations

We present the 1H, 13C and 15N NMR chemical shifts of bulk ionic liquids based on 1-butyl-3-methylimidazolium (the cation also known as 1-butyl-3-picolinium) halides (Cl-, Br- and I-) and tribromide (Br3-) salts. A characterization in solution of the analogous ICl2- and I3- salts is also reported. A series of DFT calculations has been run to predict the features of the NMR spectra of the pure ILs based on a few selected supramolecular ionic aggregates. To test the effect of temperature, and vibrational and conformational motions, only for the chloride salt, we also run first-principles molecular dynamics simulations of the ion pair in the gas phase, using the ADMP scheme (Atom Centered Density Matrix Propagation molecular dynamics model). The aim of our investigation is to test whether a simple DFT based approach of ion-pairing in ionic liquids is capable of providing reliable results and under which conditions the protocol is robust. We obtained a very good agreement between the calculated and experimental spectra for the three halides, where the bulk structure of the ILs is dominated by H-bond interactions between the X- anion (X = Cl, Br and I) and the ortho protons of the pyridinium ring (a structural arrangement not too different from the solid-state structure of pyridinium halides). In contrast, when the H-bond is weak, as in the Br3- case, a number of supramolecular arrangements exist in solution and the simple DFT calculations of a few selected cases cannot exhaustively explore the complete energy landscape. Moreover, the dynamic effects due to thermal motion, evaluated by ADMP MD simulations of the chloride salt, appear to be not very significant.

Selective hydrogenation of phenol to cyclohexanone in water over PD@N-doped carbon derived from ionic-liquid precursors

In this report, a kind of mesoporous N-doped carbon (CN-x) derived from N-containing ionic-liquid (IL) precursors were synthesized, and Pd@CN-x prepared by a simple ultrasound-assisted method showed higher catalytic activity for the selective hydrogenation of phenol and its derivatives under mild reaction conditions in water than commercial Pd@C and other common Pd heterogeneous catalysts. The catalytic activities of Pd@CN-x derived from different ILs were different, and further study into the influencing factors, including physical properties, N species of CN-x, and Pd status of Pd@CN-x, were performed. Being picky: N-Doped carbon (CN-x) derived from N-containing ionic-liquid precursors are used as Pd nanoparticle supports for the selective hydrogenation of phenol to cyclohexanone with high activity and selectivity under mild reaction conditions. The activities of the Pd@CN-x catalysts derived from a variety of ionic liquids are different, and studies on the physical properties, Pd status, and N species of the catalysts are performed.