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Pyridinium chloride

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Chemical compound
Pyridinium chloride
Pyridinium chloride
The chemical structure of pyridinium chloride
Names
IUPAC name Pyridinium chloride
Other names Pyridine hydrochloride
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.010.026 Edit this at Wikidata
EC Number
  • 211-027-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=AOJFQRQNPXYVLM-UHFFFAOYSA-N
SMILES
  • C1=CC=C=C1.
Properties
Chemical formula C5H6NCl
Molar mass 115.56 g/mol
Appearance Hygroscopic white crystals
Density 1.34 g/cm
Melting point 144 °C (291 °F; 417 K)
Boiling point Decomposes
Solubility in water 85 g / 100 mL
Solubility Soluble in chloroform, ethanol, insoluble in diethyl ether
Vapor pressure 1 (0 °C)
Acidity (pKa) 5
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Irritant
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H312, H315, H319, H332, H335
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 0 0
Flash point Non-flammable
Autoignition
temperature 		Non-flammable
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1600 mg/kg (oral, rat)
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Pyridinium chloride is an organic chemical compound with a formula of C5H5NHCl.

Preparation

Pyridinium chloride can be produced by passing hydrogen chloride in pyridine dissolved in diethyl ether. The chemical formula is as follows:

C 5 H 5 N + HCl ⟶ C 5 H 6 N + Cl − ↓ {\displaystyle {\ce {C5H5N + HCl -> C5H6N+Cl- v}}}

Acidity

Containing a pyridinium ion, pyridinium chloride has a pKa of approximately 5, slightly more acidic than that of typical amines. This is due to the hybridization of the nitrogen: the nitrogen is sp hybridized and more electronegative than those nitrogens in ammonium cations, which are sp hybridized. Hence they are stronger acids than amines and can be more easily deprotonated by bases.

References

  1. "Pyridine hydrochloride(628-13-7) MSDS Melting Point Boiling Point Density Storage Transport". ChemicalBook. Retrieved 2019-03-22.
  2. Wilson, Michael W. (2001). "Pyridinium Chloride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289x.rp287m. ISBN 9780470842898.
  3. "Pyridine: synthesis and reactivity | BrainyResort". Brainy Resort. 2016-11-08. Retrieved 2019-03-28.
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