78-73-9

Usage

Uses

Used in Pharmaceutical Industry:
Choline bicarbonate is used as a compound for protein delivery, facilitating the transport and absorption of proteins in the body.
Used in Research and Development:
Choline bicarbonate is utilized as a research tool to study a wide range of biological processes, from stem cell development to neurological disease studies, due to its role in the synthesis of essential phosphatides and neurotransmitters.
Used in Chemical Synthesis:
Choline bicarbonate serves as an alkaline intermediate, which is useful for preparing salts and choline salts, as well as in the production of surfactants.
Used as an Alkaline Catalyst:
Due to its alkaline properties, choline bicarbonate is employed as a catalyst in various chemical reactions, enhancing the efficiency and speed of these processes.

InChI:InChI=1/C5H14NO.CH2O3/c1-6(2,3)4-5-7;2-1(3)4/h7H,4-5H2,1-3H3;(H2,2,3,4)/q+1;

Synthetic route

2-(N,N-dimethylamino)ethanol (108-01-0) + carbonic acid dimethyl ester (616-38-6) → cholinium hydrogen carbonate (78-73-9)

Conditions	Yield
In methanol at 120℃; for 6h; Autoclave;	69%

Hydrogen carbonate(2-methoxycarbonyloxy-ethyl)-trimethyl-ammonium; → cholinium hydrogen carbonate (78-73-9)

Conditions	Yield
With sodium hydroxide; acetylcholine esterase at 25℃; Rate constant;

Hydrogen carbonate(2-ethoxycarbonyloxy-ethyl)-trimethyl-ammonium; → cholinium hydrogen carbonate (78-73-9)

Conditions	Yield
With sodium hydroxide; acetylcholine esterase at 25℃; Rate constant;

Octanoic acid (124-07-2) + cholinium hydrogen carbonate (78-73-9) → (2-hydroxyethyl)trimethylammonium octanoate (71501-52-5)

Conditions	Yield
In water at 20℃;	100%
In water at 20℃;
In water at 100℃; for 24h;

1-decanoic acid (334-48-5) + cholinium hydrogen carbonate (78-73-9) → (2-hydroxyethyl)trimethylammonium decanoate (133117-40-5)

Conditions	Yield
In water at 20℃;	100%
In water at 20℃;

acetic acid (64-19-7) + cholinium hydrogen carbonate (78-73-9) → choline acetate

Conditions	Yield
In water at 20℃;	100%
In water at 20℃;
In water at 20℃;

cholinium hydrogen carbonate (78-73-9) + hexanoic acid (142-62-1) → 2-hydroxy-N,N,N-trimethylethan-1-aminium hexanoate (69003-54-9)

Conditions	Yield
In water at 20℃;	100%
In water at 20℃; for 24h;	100%
In water at 24℃; for 24h;	100%

cholinium hydrogen carbonate (78-73-9) + butyric acid (107-92-6) → 2-hydroxy-N,N,N-trimethylethan-1-aminium butyrate (93458-02-7)

Conditions	Yield
In water at 20℃;	100%
In water at 20℃;
at 75℃; for 12h;

2,6-bis(difluoromethyl)-4-(6-fluoro-3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile (1287783-31-6) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxy-N,N,N-trimethylethanaminium 3,5-dicyano-2,6-bis(difluoromethyl)-4-(6-fluoro-3-methyl-1H-indazol-5-yl)-4H-pyridin-1-ide (1287783-65-6)

Conditions	Yield
In ethanol; water for 1h; Inert atmosphere; Reflux;	100%

LACTIC ACID (849585-22-4) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxyethyl-trimethylammonium 2-hydroxypropanoate

Conditions	Yield
In water at 20℃;	100%
In water at 20℃; under 760.051 Torr; for 8h;

lauric acid (143-07-7) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxyethyltrimethylammonium laurate (88371-70-4)

Conditions	Yield
In water at 20℃;	100%
In water at 100℃; for 24h;

formic acid (64-18-6) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxyethyl-trimethylammonium formate

Conditions	Yield
In water at 20℃;	100%
In water at 100℃; for 24h;
In water at 20℃; under 760.051 Torr;	9.82 g

phosphoric acid (86119-84-8, 7664-38-2) + cholinium hydrogen carbonate (78-73-9) → choline choline dihydrogen phosphate

Conditions	Yield
In water at 20℃;	100%

cholinium hydrogen carbonate (78-73-9) + dibutyl phosphate (107-66-4) → cholinium dibutyl phosphate (1241962-99-1)

Conditions	Yield
In water at 20℃;	100%

bis(2,4,4-trimethylpentyl)phosphinic acid (83411-71-6) + cholinium hydrogen carbonate (78-73-9) → choline bis(2,4,4-trimethylpentyl) phosphinate (1241963-02-9)

Conditions	Yield
In water at 20℃;	100%

geranic acid (459-80-3) + cholinium hydrogen carbonate (78-73-9) → C5H14NO(1+)*2C10H15O2(1-)

Conditions	Yield
In water at 20℃; for 12h; Solvent; Temperature;	96%

geranic acid (459-80-3) + cholinium hydrogen carbonate (78-73-9) → C5H14NO(1+)*C10H15O2(1-)*C10H16O2

Conditions	Yield
In water at 20℃; for 12.5833h; Solvent; Temperature;	96%

cis-Octadecenoic acid (112-80-1) + cholinium hydrogen carbonate (78-73-9) → (2-hydroxyethyl)trimethylammonium oleate

Conditions	Yield
In ethanol at 20℃; for 4h;	95%

geranic acid (459-80-3) + cholinium hydrogen carbonate (78-73-9) → choline geranate

Conditions	Yield
In water at 20℃; for 14h;	94.7%
In water at 20℃; for 14h;	94.7%
at 20℃; for 24h;	6.5 g
In acetone at -70 - 20℃; Temperature;

L-phenylalanine (63-91-2) + cholinium hydrogen carbonate (78-73-9) → (2-hydroxyethyl)trimethylammonium L-phenylalaninate (1361335-85-4)

Conditions	Yield
In water at 60℃; for 2h;	90%

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butyl dihydrogen phosphate + cholinium hydrogen carbonate (78-73-9) → (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butyl (2-hydroxyethyl)trimethylammonium hydrogen phosphate dihydrate

Conditions	Yield
In water; acetone	74%

(R)-2-methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile (1287783-22-5) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxy-N,N,N-trimethylethanaminium (4R)-3,5-dicyano-2-methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-4H-pyridin-1-ide (1287783-57-6)

Conditions	Yield
In ethanol; water for 0.666667h; Inert atmosphere; Reflux;	64%

2,6-bis(difluoromethyl)-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile (1287783-30-5) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxy-N,N,N-trimethylethanaminium 3,5-dicyano-2,6-bis(difluoromethyl)-4-(3-methyl-1H-indazol-5-yl)-4H-pyridin-1-ide (1287783-68-9)

Conditions	Yield
In ethanol; water for 1h; Inert atmosphere; Reflux;	54%

(S)-2-methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile (1287783-23-6) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxy-N,N,N-trimethylethanaminium (4S)-3,5-dicyano-2-methyl-4-(3-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-4H-pyridin-1-ide (1287783-53-2)

Conditions	Yield
In ethanol; water for 0.666667h; Inert atmosphere; Reflux;	51%

3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-[1,2,4]thiadiazol-5-yl-cyanamide (143429-64-5) + cholinium hydrogen carbonate (78-73-9) → <3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-1,2,4-thiadiazol-5-yl>cyanamide choline salt (143429-66-7)

Conditions	Yield
In methanol; water for 1h; Yield given;

[5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methylene]-4,5-dihydro-4-oxo-2-thiazolyl]cyanamide + cholinium hydrogen carbonate (78-73-9) → [5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro-4-oxo-2-thiazolyl]cyanamide, choline salt

cholinium hydrogen carbonate (78-73-9) → choline dihydrogen phosphite (947138-30-9)

Conditions	Yield
With phosphonic Acid In water for 4h;

propionic acid (802294-64-0) + cholinium hydrogen carbonate (78-73-9) → 2-hydroxy-N,N,N-trimethylethan-1-aminium propionate

Conditions	Yield
In water at 20℃;
In water at 20℃;

cholinium hydrogen carbonate (78-73-9) + isobutyric Acid (79-31-2) → cholinium 2-methylpropanoate (115307-87-4)

Conditions	Yield
In water at 20℃;

cholinium hydrogen carbonate (78-73-9) + valeric acid (109-52-4) → 2-hydroxy-N,N,N-trimethylethan-1-aminium pentanoate (1246854-87-4)

Conditions	Yield
In water at 20℃;

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 143429-66-7 <3-<3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl>-1,2,4-thiadiazol-5-yl>cyanamide choline salt 
• 71501-52-5 (2-hydroxyethyl)trimethylammonium octanoate 
• 14586-35-7 choline acetate 
• 83846-92-8 choline choline dihydrogen phosphate 
• 1321816-57-2 3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4- d]pyrimidine-5-carboxylic acid (2-hydroxyethyl)trimethylammonium 
• 1361335-85-4 (2-hydroxyethyl)trimethylammonium L-phenylalaninate 
• 93857-07-9 choline 2,5-dihydroxybenzoate 
• 1927-06-6 choline bromide 
• 827027-25-8 N,N,N-trimethyl-N-(2-hydroxyethyl)ammonium bis(trifluoromethanesulfonyl)imide 

Relevant academic research and scientific papers

Synthesis and properties of room-temperature choline carboxylate zwitterionic ionic liquids as potential electrolytes

Choline carboxylate zwitterions were prepared by two different synthetic routes through esterification of choline salts with a range of anhydrides. Their conjugation with lithium bis(trifluoromethylsulfonyl) imide resulted in the formation of stable room-temperature ionic liquids. In view of their use as potential electrolytes the physicochemical characterization of these attractive ionic liquids was performed. These compounds presented a glass transition temperature between -43 and -34 °C, good thermal stability up to 2248C, densities above 1.44 gcm-3 at 25°C, and viscosities between 3.56 and 12.27 Pa s at 258C. In terms of conductivity the most promising ionic liquid showed an excellent conductivity between 8.66 105 Scm-1 at 258C and 1.8010-3 Scm-1 at 908C. These zwitterionic ionic liquids maintained a liquid state, and no dissociation was observed even after six months of storage at room temperature.