4-(Chloromethyl)pyridine hydrochloride

Base Information

• Chemical Name: 4-(Chloromethyl)pyridine hydrochloride
• CAS No.: 1822-51-1
• Molecular Formula: C6H6ClN^.HCl
• Molecular Weight: 164.034
• Hs Code.: 29333999
• European Community (EC) Number: 217-350-7
• NSC Number: 66483
• DSSTox Substance ID: DTXSID00171264
• ChEMBL ID: CHEMBL4593693
• Mol file: 1822-51-1.mol

Synonyms:Pyridine,4-(chloromethyl)-, hydrochloride (6CI,7CI,8CI,9CI);4-(Chloromethyl)pyridinehydrochloride;4-(Chloromethyl)pyridinium chloride;4-Chloromethylpyridinehydrochloride salt;4-Picolyl chloride hydrochloride;4-Pyridylmethyl chloridehydrochloride;

Chemical Property of 4-(Chloromethyl)pyridine hydrochloride

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.257mmHg at 25°C
• Melting Point: 166-173 °C(lit.)
• Refractive Index: 1.53
• Boiling Point: 212 °C at 760 mmHg
• Flash Point: 102 °C
• PSA: 12.89000
• Density: 1.156g/cm³
• LogP: 2.62240
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Water Solubility.: 750 g/L (20 ºC)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 162.9955546
• Heavy Atom Count: 9
• Complexity: 59.5

Purity/Quality:

99% ^*data from raw suppliers

4-(Chloromethyl)pyridine Hydrochloride >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-4-22-36/37/38
• Safety Statements: 26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN=CC=C1CCl.Cl
• Uses: It finds its application as a reagent for protection of carboxyl termini of peptides as 4-picolyl esters, providing a polar 'handle' which aids in separation and purification of the peptide. The group can be introduced in the presence of a base, e.g. tetramethylguanidine, is stable to acid-catalyzed removal of Cbz protecting group and can be removed by base, Na in liquid ammonia or catalytic hydrogenolysis. It is also applied in conjunction with Amberlyst?15 resin in peptide synthesis. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Technology Process of 4-(Chloromethyl)pyridine hydrochloride

There total 7 articles about 4-(Chloromethyl)pyridine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

pyridine-4-methanol (586-95-8) → 4-picolylchloride hydrochloride (1822-51-1)

Guidance literature:

With thionyl chloride; In acetonitrile; at 50 ℃; for 1h;

Reference yield: 76.0%

4-(phenoxymethyl)pyridine (63608-12-8) + 4-pyridinemethanol hydrochloride (62302-28-7) → 4-picolylchloride hydrochloride (1822-51-1)

Guidance literature:

With thionyl chloride; In benzene;

Reference yield:

4-methylpyridine-1-oxide (1003-67-4) → 2-chloro-4-picoline (3678-62-4) + 4-picolylchloride hydrochloride (1822-51-1)

Guidance literature:

With diisopropylamine; trichloromethyl chloroformate; In dichloromethane; at -40 - 20 ℃;

DOI:10.1081/SCC-120028642

upstream raw materials:

4-methylpyridine-1-oxide

pyridine-4-methanol

triethylamine

4-(phenoxymethyl)pyridine

Downstream raw materials:

4-((allyloxy)methyl)pyridine

4-(methoxymethyl)pyridine

4-(ethoxymethyl)pyridine

4-(phenoxymethyl)pyridine

Refernces

Synthesis, optical properties and protonation of chlorophyll derivatives appending a pyridyl group in the C3-substituent

10.1016/j.dyepig.2015.03.006

The research focuses on the synthesis, optical properties, and protonation of chlorophyll-a (Chl-a) derivatives that have a 2-(2/3/4-pyridyl)ethenyl group at the C3 position. The derivatives were synthesized using the Wittig reaction on methyl pyropheophorbide-d, which involved reactants such as 2/3/4-(chloromethyl)pyridine hydrochloride and triphenylphosphine. The resulting olefins were then subjected to catalytic hydrogenation using PtO2 in a mixed solvent of acetone and ethanol to yield the corresponding regioisomers. The optical properties of these derivatives were analyzed using visible absorption and fluorescence emission spectra, with the longest wavelength (Qy) maxima shifting bathochromically based on the linker between the chlorin and pyridyl moieties. Protonations were conducted by titrating the synthetic chlorophyll-pyridine conjugates with trifluoroacetic acid in chloroform, and the resulting visible spectral changes indicated the order of protonation. The analyses included the determination of association constants, high-resolution mass spectrometry (HRMS), and nuclear magnetic resonance (NMR) spectroscopy.