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Names | |
---|---|
IUPAC name
Choline hydroxide
| |
Systematic IUPAC name
2-Hydroxy-N,N,N-trimethylethanaminium hydroxide
[1] | |
Other names | |
Identifiers | |
3D model (
JSmol)
|
|
Abbreviations | ChOH [2] |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.206 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
[(CH3)3NCH2CH2OH]+OH− | |
Molar mass | 121.180 g·mol−1 |
Appearance | Viscous colorless deliquescent liquid [1] [3] or white granular powder [4] |
Odor | Unpleasant, like trimethylamine [3] |
Density | 1.073 g/cm3 at 25 °C (46% water solution by weight) [5] |
Very soluble [3] | |
Solubility | 48-50% solution of choline hydroxide in water (by weight) is insoluble in
toluene.
[6] Choline hydroxide
is soluble in ethanol, [3] insoluble in diethyl ether and chloroform. [7] |
Refractive index (nD)
|
1.4304 (46% water solution by weight) [5] |
Structure | |
Tetrahedral at the nitrogen atom | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
Corrosive |
GHS labelling: | |
![]() ![]() ![]() | |
Danger | |
H314, H335, H372 | |
P260, P261, P264, P270, P271, P280, P301+P330+P331, P302, P304+P340, P305, P316, P317, P319, P321, P338, P361, P363, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 92 °F (33 °C) [4] |
380 °C (716 °F) [6] | |
Lethal dose or concentration (LD, LC): | |
LD50 (
median dose)
|
21.4 mg/kg (mouse, intravenous) [1] |
Related compounds | |
Other
anions
|
Choline chloride |
Other
cations
|
Tetraethylammonium hydroxide |
Related compounds
|
Choline |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Choline hydroxide is an organic compound with the chemical formula [(CH3)3NCH2CH2OH]+OH−. It is also known as choline base. It is used as solutions in water or alcohols, which are colorless and very alkaline.
It is hygroscopic and thus often encountered as a colorless viscous hydrated syrup that smells of trimethylamine (TMA). Aqueous solutions of choline are stable, but the compound slowly breaks down to ethylene glycol, polyethylene glycols, and TMA. [3]
Choline hydroxide is a quaternary ammonium salt, consisting of choline cations ([(CH3)3NCH2CH2OH]+) and hydroxide anions (OH−). It is bifunctional compound, meaning, it contains both quaternary ammonium functional group and a hydroxyl functional group. Choline hydroxide forms an ionic liquid.
The cation of this salt, choline, occurs in nature in living beings. [8]
Choline hydroxide is used in industry as a pH regulating agent [1] and as an eco-friendly, biodegradable, recyclable and efficient catalyst with high yields for synthesis of certain organic compounds (2-amino-3-nitro-4H-chromene derivatives) in an aqueous solution at room temperatures. [2]
Choline hydroxide irritates skin, eyes and respiratory system. It can cause serious injuries to the eyes. Causes serious skin and eye burns. Inhalation of this chemical may cause dyspnea and corrosive injuries to upper respiratory system and lungs, which can lead to pneumonia. [1] [6] [5] May react violently with strong oxidizing agents. [4]
![]() | |
Names | |
---|---|
IUPAC name
Choline hydroxide
| |
Systematic IUPAC name
2-Hydroxy-N,N,N-trimethylethanaminium hydroxide
[1] | |
Other names | |
Identifiers | |
3D model (
JSmol)
|
|
Abbreviations | ChOH [2] |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.206 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
[(CH3)3NCH2CH2OH]+OH− | |
Molar mass | 121.180 g·mol−1 |
Appearance | Viscous colorless deliquescent liquid [1] [3] or white granular powder [4] |
Odor | Unpleasant, like trimethylamine [3] |
Density | 1.073 g/cm3 at 25 °C (46% water solution by weight) [5] |
Very soluble [3] | |
Solubility | 48-50% solution of choline hydroxide in water (by weight) is insoluble in
toluene.
[6] Choline hydroxide
is soluble in ethanol, [3] insoluble in diethyl ether and chloroform. [7] |
Refractive index (nD)
|
1.4304 (46% water solution by weight) [5] |
Structure | |
Tetrahedral at the nitrogen atom | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
|
Corrosive |
GHS labelling: | |
![]() ![]() ![]() | |
Danger | |
H314, H335, H372 | |
P260, P261, P264, P270, P271, P280, P301+P330+P331, P302, P304+P340, P305, P316, P317, P319, P321, P338, P361, P363, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 92 °F (33 °C) [4] |
380 °C (716 °F) [6] | |
Lethal dose or concentration (LD, LC): | |
LD50 (
median dose)
|
21.4 mg/kg (mouse, intravenous) [1] |
Related compounds | |
Other
anions
|
Choline chloride |
Other
cations
|
Tetraethylammonium hydroxide |
Related compounds
|
Choline |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Choline hydroxide is an organic compound with the chemical formula [(CH3)3NCH2CH2OH]+OH−. It is also known as choline base. It is used as solutions in water or alcohols, which are colorless and very alkaline.
It is hygroscopic and thus often encountered as a colorless viscous hydrated syrup that smells of trimethylamine (TMA). Aqueous solutions of choline are stable, but the compound slowly breaks down to ethylene glycol, polyethylene glycols, and TMA. [3]
Choline hydroxide is a quaternary ammonium salt, consisting of choline cations ([(CH3)3NCH2CH2OH]+) and hydroxide anions (OH−). It is bifunctional compound, meaning, it contains both quaternary ammonium functional group and a hydroxyl functional group. Choline hydroxide forms an ionic liquid.
The cation of this salt, choline, occurs in nature in living beings. [8]
Choline hydroxide is used in industry as a pH regulating agent [1] and as an eco-friendly, biodegradable, recyclable and efficient catalyst with high yields for synthesis of certain organic compounds (2-amino-3-nitro-4H-chromene derivatives) in an aqueous solution at room temperatures. [2]
Choline hydroxide irritates skin, eyes and respiratory system. It can cause serious injuries to the eyes. Causes serious skin and eye burns. Inhalation of this chemical may cause dyspnea and corrosive injuries to upper respiratory system and lungs, which can lead to pneumonia. [1] [6] [5] May react violently with strong oxidizing agents. [4]