Choline chloride

Choline chloride
IUPAC name 2-hydroxy-N,N,N-trimethylethanaminium chloride OR (2-hydroxyethyl)trimethylammonium chloride
Identifiers
CAS number	67-48-1 Y
PubChem	522265
ChemSpider	5974 Y
UNII	45I14D8O27 Y
ChEBI	CHEBI:133341 N
ChEMBL	CHEMBL282468 N
Jmol-3D images	Image 1
SMILES [Cl-].OCC[N+](C)(C)C
InChI InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1 Y Key: SGMZJAMFUVOLNK-UHFFFAOYSA-M Y InChI=1/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1 Key: SGMZJAMFUVOLNK-REWHXWOFAH
Properties
Molecular formula	C5H14ClNO
Molar mass	139.62 g mol−1
Appearance	White or deliquescent crystals
Melting point	302 °C (decomposes)
Solubility in water	very soluble (>650 g/l)[1]
Hazards
MSDS	External MSDS
NFPA 704	0 2 0
N chloride (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Choline chloride is an organic compound and a quaternary ammonium salt. It has a choline cation with chloride anion. Alternative names are hepacholine, biocolina and lipotril.

Synthesis

In the laboratory choline can be prepared by methylation of dimethylethanolamine with methyl chloride.

In the industrial Davy Process Technology route choline chloride is produced from ethylene oxide, hydrochloric acid, and trimethylamine,^[2] or from the pre-formed salt:^[3]

Applications

Choline chloride is mass produced and is an important additive in feed especially for chickens where it accelerates growth. With urea it forms a deep eutectic solvent. Other commercial choline salts are choline hydroxide and choline bitartrate. In foodstuffs the compound is often present as phosphatidylcholine.

References

1. ^ "Chemical Safety Information from Intergovernmental Organizations - Choline Chloride". http://www.inchem.org/documents/sids/sids/67481.pdf. 
2. ^ Davy Process Technology
3. ^ "Choline chloride". Screening Information Data Set (SIDS) for High Production Volume Chemicals. IPCS INCHEM. http://www.inchem.org/documents/sids/sids/67481.pdf.