125652-55-3

Basic information

• Product Name: 3-METHYL-N-BUTYLPYRIDINIUM CHLORIDE
• Synonyms: 3-METHYL-N-BUTYLPYRIDINIUM CHLORIDE;N-BUTYL-3-METHYLPYRIDINIUM CHLORIDE;1-Butyl-3-methylpyridinium Chloride;N-butyl-3-metylpyridinium chloride;B3MePyCl
• CAS NO: 125652-55-3
• Molecular Formula: C₁₀H₁₆N*Cl
• Molecular Weight: 185.69
• EINECS: 1533716-785-6
• Mol File: 125652-55-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 3-METHYL-N-BUTYLPYRIDINIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-N-BUTYLPYRIDINIUM CHLORIDE(125652-55-3)
• EPA Substance Registry System: 3-METHYL-N-BUTYLPYRIDINIUM CHLORIDE(125652-55-3)

Safety Data

• Hazardous Substances Data: 125652-55-3(Hazardous Substances Data)

Usage

General Description

3-Methyl-N-butyldyridinium chloride is a chemical compound with the molecular formula C9H14ClN. It is a quaternary ammonium compound, and is primarily used as an ionic liquid and in organic synthesis. 3-METHYL-N-BUTYLPYRIDINIUM CHLORIDE is often used as a catalyst in various chemical reactions, and has been investigated for its potential applications in electrochemical processes and as an anti-microbial agent. It is also known for its unique physicochemical properties, such as low volatility and high thermal stability, making it useful in a variety of industrial and research settings.

InChI:InChI=1/C10H16N.ClH/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

Synthetic route

3-Methylpyridine (108-99-6) + n-Butyl chloride (109-69-3) → 1-butyl-3-methylimidazolium chloride (125652-55-3)

Conditions	Yield
at 90℃; for 24h;	93%
at 110℃;	85%
for 33h; Heating / reflux;
In toluene Inert atmosphere; Reflux;
In toluene at 20 - 130℃; Inert atmosphere;

1-butyl-3-methylimidazolium chloride (125652-55-3) → 1-butyl-3-methyl-pyridinium dichloroiodate

Conditions	Yield
With Iodine monochloride In dichloromethane; water at 0 - 20℃; for 1h;	100%
With Iodine monochloride In dichloromethane; water at 0 - 20℃; for 1h;	98%
With Iodine monochloride In dichloromethane; water at 20℃; for 1h; Cooling with ice;	98%

1-butyl-3-methylimidazolium chloride (125652-55-3) → 1-butyl-3-methyl-pyridinium chlorodiiodide

Conditions	Yield
With iodine In dichloromethane; water at 0 - 20℃; for 24h;	100%

1-butyl-3-methylimidazolium chloride (125652-55-3) → 1-butyl-3-methylpyridinium trichloride

Conditions	Yield
With chlorine In methanol at 0 - 20℃; for 3h;	100%

1-butyl-3-methylimidazolium chloride (125652-55-3) + sodium caprylate (1984-06-1) → 1-butyl-3-methylpyridinium octanoate

Conditions	Yield
In water at 40℃; Flow reactor;	96%

1-butyl-3-methylimidazolium chloride (125652-55-3) → 1-butyl-3-methylpyridinium chlodiiodide

Conditions	Yield
With iodine In dichloromethane; water at 0 - 20℃; for 24h;	95%

1-butyl-3-methylimidazolium chloride (125652-55-3) + K[HB(CN)3] → 1-butyl-3-methylpyridinium hydrido-tricyano-borate (1415416-96-4) + potassium chloride

Conditions	Yield
With water	A 91% B n/a

1-butyl-3-methylimidazolium chloride (125652-55-3) + sodium butyrate (156-54-7) → 1-butyl-3-methylpyridinium butanoate

Conditions	Yield
In water at 40℃; Flow reactor;	91%

1-butyl-3-methylimidazolium chloride (125652-55-3) + sodium dicyanodihydridoborate (88503-36-0) → 1-butyl-3-methylpyridinium dicyanodihydridoborate (1415022-39-7)

Conditions	Yield
In water	90%
With sodium sulfate In water

1-butyl-3-methylimidazolium chloride (125652-55-3) + sodium dicyanamide (1934-75-4) → 1-butyl-3-methylpyridinium dicyanoazanide (712355-12-9)

Conditions	Yield
In water at 20℃;	87%

1-butyl-3-methylimidazolium chloride (125652-55-3) + potassium dicyanamide (34723-47-2) + cobalt(II) chloride (7646-79-9) → (N-butyl-3-methylpyridinium)2 Co(dicyanamido)4

Conditions	Yield
In acetone at 75℃; Reflux;	87%

1-butyl-3-methylimidazolium chloride (125652-55-3) + C16H34O4P(1-)*Na(1+) (847448-65-1) → C10H16N(1+)*C16H34O4P(1-) (1323126-07-3)

Conditions	Yield
In acetone Reflux;

1-butyl-3-methylimidazolium chloride (125652-55-3) + sodium O,Se-dimethylphosphoroselenoate (1274452-24-2) → 1-butyl-3-methylpyridinium O,Se-dimethylphosphoroselenoate (1331734-78-1)

Conditions	Yield
In acetonitrile at 20℃; Sonication;	15.19 g

1-butyl-3-methylimidazolium chloride (125652-55-3) + sodium O,S-dimethyl phosphorothioate (32586-90-6) → 1-butyl-3-methylpyridinium O,S-dimethylphosphorothioate (1331734-68-9)

Conditions	Yield
In acetonitrile at 20℃; Sonication;	26.45 g

1-butyl-3-methylimidazolium chloride (125652-55-3) + zinc(II) chloride (7646-85-7) → 1-butyl-3-methylpyridinium zinc(II) chloride

Conditions	Yield
at 100℃;

1-butyl-3-methylimidazolium chloride (125652-55-3) + zinc(II) chloride (7646-85-7) → 1-butyl-3-methylpyridinium zinc(II) chloride

Conditions	Yield
at 100℃;

1-butyl-3-methylimidazolium chloride (125652-55-3) + zinc(II) chloride (7646-85-7) → 1-butyl-3-methylpyridinium zinc(II) chloride

Conditions	Yield
at 100℃;

1-butyl-3-methylimidazolium chloride (125652-55-3) + zinc(II) chloride (7646-85-7) → 1-butyl-3-methylpyridinium zinc(II) chloride

Conditions	Yield
at 100℃;

Upstream product

• 108-99-6 3-Methylpyridine 
• 109-69-3 n-Butyl chloride 

Downstream Products

• 712355-12-9 1-butyl-3-methylpyridinium dicyanoazanide 

Relevant articles and documents

Synthesis and dissolving power of 1-Alkyl-3-methylpyridinium-based ionic liquids

1-Alkyl-3-methylpyridinium-based ionic liquids with substituents from C2 to C10 and anions Cl- and Br- were synthesized, and their dissolving power toward the cellulose was investigated. The results of quantum-chemical calculations of molecules of ionic liquids are presented.

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.

Alkylpyridiniumdicyanamides as polar solvents

Alkylpyridinium cyanamide compounds (I) are new. Alkylpyridinium cyanamide compounds of formula (I) are new. R n 1>CN or 1-20C alkyl; R 2>1-20C alkyl; and n : 0-3. An independent claim is also included for the preparation of (I). [Image].