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Tetrapropylammonium chloride

Chemical compound From Wikipedia, the free encyclopedia

Tetrapropylammonium chloride is an organic compound with the chemical formula [(CH3CH2CH2)4N]Cl. It is a white, very hygroscopic crystalline solid.[2][6] Tetrapropylammonium chloride is a quaternary ammonium salt. It consists of tetrapropylammonium cations [(CH3CH2CH2)4N]+ and chloride anions Cl−.

Quick facts Names, Identifiers ...
Tetrapropylammonium chloride
Tetrapropylammonium chloride structural formula
Names
IUPAC name
Tetrapropylazanium chloride[1]
Other names
  • 1-Propanaminium, N,N,N-tripropyl-, chloride[1]
  • TPAC[2]
  • TPACl[3]
  • TPrACl[4]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.887 Edit this at Wikidata
EC Number
  • 227-375-5
  • InChI=1S/C12H28N.ClH/c1-5-9-13(10-6-2,11-7-3)12-8-4;/h5-12H2,1-4H3;1H/q+1;/p-1
    Key: FBEVECUEMUUFKM-UHFFFAOYSA-M
  • CCC[N+](CCC)(CCC)CCC.[Cl-]
Properties
[(CH3CH2CH2)4N]Cl
Molar mass 221.81 g·mol−1
Appearance White crystalline solid[5][3][1]
Odor Odorless[1]
Melting point 240–242 °C (464–468 °F; 513–515 K)[5]
Soluble[3]
Solubility Soluble in polar solvents like alcohols.[3] Soluble in acetone.[4]
Structure
Tetrahedral at N
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Serious eye irritation
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, 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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and properties

Tetrapropylammonium chloride is synthesized by reaction between tripropylamine and 1-chloropropane.[2]

(CH3CH2CH2)3N + CH3CH2CH2Cl → [(CH3CH2CH2)4N]Cl

The density of a concentrated aqueous solution of tetrapropylammonium chloride is less than that of a dilute solution at the same temperature.[6]

The fully deuterated form of tetrapropylammonium chloride, [(CD3CD2CD2)4N]Cl, is also a white solid.[3]

Uses

Tetrapropylammonium chloride is used as antimicrobial agent.[3] It is also widely used as a phase-transfer catalyst in organic synthesis, facilitating the transfer of reactants between immiscible phases. It is used to stabilize emulsions and enhance solubility of hydrophobic compounds in aqueous solutions.[2][3]

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