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Choline hydroxide

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Organic chemical compound
Choline hydroxide
Choline hydroxide
Names
IUPAC name Choline hydroxide
Systematic IUPAC name 2-Hydroxy-N,N,N-trimethylethanaminium hydroxide
Other names
  • Choline base
  • Ethanaminium, 2-hydroxy-N,N,N-trimethyl-, hydroxide (1:1)
  • Gossypine
  • (2-Hydroxyethyl)trimethylammonium hydroxide
  • 2-Hydroxyethyl(trimethyl)azanium hydroxide
  • Sincaline
Identifiers
CAS Number
3D model (JSmol)
Abbreviations ChOH
ChEMBL
ChemSpider
ECHA InfoCard 100.004.206 Edit this at Wikidata
EC Number
  • 204-625-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H14NO.H2O/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H2/q+1;/p-1Key: KIZQNNOULOCVDM-UHFFFAOYSA-M
SMILES
  • C(C)(C)CCO.
Properties
Chemical formula [(CH3)3NCH2CH2OH]OH
Molar mass 121.180 g·mol
Appearance Viscous colorless deliquescent liquid or white granular powder
Odor Unpleasant, like trimethylamine
Density 1.073 g/cm at 25 °C (46% water solution by weight)
Solubility in water Very soluble
Solubility 48-50% solution of choline hydroxide in water (by weight) is insoluble in toluene. Choline hydroxide

is soluble in ethanol, insoluble in diethyl ether and chloroform.

Refractive index (nD) 1.4304 (46% water solution by weight)
Structure
Coordination geometry Tetrahedral at the nitrogen atom
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Corrosive
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H314, H335, H372
Precautionary statements 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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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
3 0 0
Flash point 92 °F (33 °C)
Autoignition
temperature 		380 °C (716 °F)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 21.4 mg/kg (mouse, intravenous)
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 , 100 kPa). Infobox references
Chemical compound

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.

Properties

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.

Chemistry

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.

Occurrence

The cation of this salt, choline, occurs in nature in living beings.

Uses

Choline hydroxide is used in industry as a pH regulating agent 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.

A chemical reaction of various salicylaldehydes (2-hydroxybenzaldehydes) with (E)-N-methyl-1-(methylthio)-2-nitroethenamine, in the presence of a basic ionic liquid catalyst such as choline hydroxide, at room temperature in an aqueous medium, produces 2-amino-3-nitro-4H-chromene derivatives (yields up to 83-96%).

Safety

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. May react violently with strong oxidizing agents.

References

  1. ^ "Choline hydroxide". pubchem.ncbi.nlm.nih.gov.
  2. ^ Krishnammagari, Suresh Kumar; Lim, Kwon Taek; Cho, Byung Gwon; Tae Jeong, Yeon (January 1, 2018). "Choline hydroxide: An efficient and biodegradable catalyst for the synthesis of 2-amino-3-nitro-4H-chromene derivatives in an aqueous medium". Phosphorus, Sulfur, and Silicon and the Related Elements. 193 (9): 574–581. doi:10.1080/10426507.2018.1469489. S2CID 105825055 – via www.sciencedirect.com.
  3. ^ Kirk RE, et al. (2000). Kirk-Othmer encyclopedia of chemical technology. Vol. 6 (4th ed.). John Wiley & Sons. pp. 100–102. ISBN 9780471484943.
  4. ^ "Choline hydroxide | 123-41-1". ChemicalBook.
  5. ^ https://www.sigmaaldrich.com/GB/en/product/aldrich/292257
  6. ^ https://www.carlroth.com/medias/SDB-3406-GB-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wzMTA3NDN8YXBwbGljYXRpb24vcGRmfHNlY3VyaXR5RGF0YXNoZWV0cy9oMjcvaGFmLzkwNjA5OTcxMzY0MTQucGRmfGVmOTEwZTlkM2E0YTVjN2U4NWI0YzUxZWExNjRkYzFlYmE2YzYzMzRmOTU1NTc4MDA1NTBkZDkxY2U4NDY3M2Y
  7. Rucker RB, Zempleni J, Suttie JW, McCormick DB (2007). Handbook of vitamins (4th ed.). Taylor & Francis. pp. 459–477. ISBN 9780849340222.
  8. "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. February 2015. Retrieved 11 November 2019.
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