34004-36-9

Basic information

• Product Name: (2,3-dihydroxypropyl)trimethylammonium chloride
• Synonyms: (2,3-dihydroxypropyl)trimethylammonium chloride;1-Propanaminium, 2,3-dihydroxy-N,N,N-trimethyl-, chloride;2,3-Dihydroxy-N,N,N-trimethylpropan-1-aminium chloride
• CAS NO: 34004-36-9
• Molecular Formula: C₆H₁₆NO₂*Cl
• Molecular Weight: 169.64974
• EINECS: 251-783-2
• Mol File: 34004-36-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (2,3-dihydroxypropyl)trimethylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2,3-dihydroxypropyl)trimethylammonium chloride(34004-36-9)
• EPA Substance Registry System: (2,3-dihydroxypropyl)trimethylammonium chloride(34004-36-9)

Safety Data

• Hazardous Substances Data: 34004-36-9(Hazardous Substances Data)

Usage

General Description

(2,3-dihydroxypropyl)trimethylammonium chloride, also known as choline chloride, is a quaternary ammonium salt commonly used as a nutritional supplement and as a component of various pharmaceutical products. It is a water-soluble compound with the chemical formula C5H14ClNO. Choline chloride is an essential nutrient that plays a crucial role in various physiological functions, such as cell membrane integrity, nerve impulse transmission, and lipid metabolism. It is also used as a feed additive in animal nutrition to promote healthy growth and development. In pharmaceutical applications, choline chloride is used as a cholinergic agent and as a precursor to the neurotransmitter acetylcholine. Additionally, it has antimicrobial properties and is used in some industrial and agricultural products.

InChI:InChI=1/C6H16NO2.ClH/c1-7(2,3)4-6(9)5-8;/h6,8-9H,4-5H2,1-3H3;1H/q+1;/p-1

Synthetic route

N-(3-chloro-2-hydroxypropyl)trimethylammonium chloride → N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9)

Conditions	Yield
With sodium hydroxide In water at 20 - 50℃; for 14h;	97%

3-monochloro-1,2-propanediol (96-24-2) + trimethylamine (75-50-3) → N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9)

Conditions	Yield
In water at 90℃; for 16h;	91.2%
at 100℃;
at 100℃;

oxiranyl-methanol (556-52-5) + trimethylamine hydrochloride (593-81-7) → N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol at 20℃; for 12h;	71%

2-chloro-ethanol (107-07-3) + trimethylamine (75-50-3) → N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9)

Conditions	Yield
In methanol; ethanol at 0 - 68℃; for 10h; Inert atmosphere;

cis-Octadecenoic acid (112-80-1) + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride (477274-39-8, 132172-61-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;	84.3%

(Z)-9-octadecenoyl chloride (112-77-6) + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride (477274-39-8, 132172-61-3)

Conditions	Yield
With trimethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 9h; Inert atmosphere;	46.5%

N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) + aq. barium hydroxide solution → trimethylamine (75-50-3)

sodium acetate (127-09-3) + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) + acetic anhydride (108-24-7) → trimethyl-<β.γ-diacetoxy-propyl>-ammonium chloride

hydrogen iodide (10034-85-2) + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) + red phosphorus → trimethyl-<β.γ diiodide-propyl>-ammonium iodide + trimethyl--ammonium iodide

N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → N-(3-chloro-2-hydroxypropyl)trimethylammonium chloride

Conditions	Yield
With thionyl chloride In N-methyl-acetamide
With thionyl chloride In N-methyl-acetamide

N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) + 3-monochloro-1,2-propanediol (96-24-2) → 1-trimethylammonium-2,5,6-trihydroxydipropyl ether chloride + 1-trimethylammonium-2-hydroxymethyl-4,5-dihydroxypropyl ethyl ether chloride

Conditions	Yield
With sodium hydroxide In water at 20℃; pH=< 9;
Stage #1: N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride With sodium hydride at 20℃; Stage #2: 3-monochloro-1,2-propanediol at 20℃; pH=< 9;

5-chloromethyl-2,2-dimethyl-1,3-dioxolane (4362-40-7) + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → 1-trimethylammonium-2,5,6-trihydroxydipropyl ether chloride + 1-trimethylammonium-2-hydroxymethyl-4,5-dihydroxypropyl ethyl ether chloride

Conditions	Yield
Stage #1: 5-chloromethyl-2,2-dimethyl-1,3-dioxolane; N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride With sodium hydroxide In water at 20℃; pH=< 9; Stage #2: With acetic acid In diethyl ether; water at 20℃; for 16h;

C14H15ClF12O + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → (2,3-bis((3,4,4,5,5,6,6,7,7,8,8-undecafluorotetradecen-2-oyl)oxy)prop-1-yl)-N,N,N-trimethylammonium chloride + (2,3-bis(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorotetradecanoyloxy)prop-1-yl)-N,N,N-trimethylammonium chloride (1208999-57-8)

Conditions	Yield
With pyridine In tetrahydrofuran; dichloromethane at 20℃; Sonication;

C14H15ClF12O + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → (2,3-bis((3,4,4,5,5,6,6,7,7,8,8-undecafluorotetradecen-2-oyl)oxy)prop-1-yl)-N,N,N-trimethylammonium chloride

Conditions	Yield
Stage #1: C14H15ClF12O; N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride With pyridine In tetrahydrofuran; dichloromethane at 20℃; Sonication; Stage #2: With triethylamine In tetrahydrofuran; dichloromethane; acetonitrile at 20℃; for 2h;	20 mg

C16H23ClF8O + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → (2,3-bis((3,4,4,5,5,6,6-heptafluorohexadecen-2-oyl)oxy)prop-1-yl)-N,N,N-trimethylammonium chloride + (2,3-bis(3,3,4,4,5,5,6,6-octafluorohexadecanoyloxy)prop-1yl)-N,N,N-trimethylammonium chloride (1208999-58-9)

Conditions	Yield
With pyridine In tetrahydrofuran; dichloromethane at 20℃; Sonication;

C16H23ClF8O + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → (2,3-bis((3,4,4,5,5,6,6-heptafluorohexadecen-2-oyl)oxy)prop-1-yl)-N,N,N-trimethylammonium chloride

Conditions	Yield
Stage #1: C16H23ClF8O; N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride With pyridine In tetrahydrofuran; dichloromethane at 20℃; Sonication; Stage #2: With triethylamine In tetrahydrofuran; dichloromethane; acetonitrile at 20℃; for 2h;	6 mg

C18H23ClF12O + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → (2,3-bis((3,4,4,5,5,6,6,7,7,8,8-undecafluorooctadecen-2-oyl)oxy)prop-1-yl)-N,N,N-trimethylammonium chloride + (2,3-bis(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorooctadecanoyloxy)prop-1-yl)-N,N,N-trimethylammonium chloride (1208999-59-0)

Conditions	Yield
With pyridine In tetrahydrofuran; dichloromethane at 20℃; Sonication;

C18H23ClF12O + N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) → (2,3-bis((3,4,4,5,5,6,6,7,7,8,8-undecafluorooctadecen-2-oyl)oxy)prop-1-yl)-N,N,N-trimethylammonium chloride

Conditions	Yield
Stage #1: C18H23ClF12O; N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride With pyridine In tetrahydrofuran; dichloromethane at 20℃; Sonication; Stage #2: With triethylamine In tetrahydrofuran; dichloromethane; acetonitrile at 20℃; for 2h;	10 mg

N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium chloride (34004-36-9) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → N-[(2,3-dihydroxy)prop-1-yl]-N,N,N-trimethylammonium bistriflamide (1613460-36-8)

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

Upstream product

• 556-52-5 oxiranyl-methanol 
• 593-81-7 trimethylamine hydrochloride 
• 101396-91-2 N-(3-chloro-2-hydroxypropyl)trimethylammonium chloride 
• 96-24-2 3-monochloro-1,2-propanediol 
• 75-50-3 trimethylamine 
• 107-07-3 2-chloro-ethanol 

Downstream Products

• 1208999-57-8 (2,3-bis(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorotetradecanoyloxy)prop-1-yl)-N,N,N-trimethylammonium chloride 
• 1208999-58-9 (2,3-bis(3,3,4,4,5,5,6,6-octafluorohexadecanoyloxy)prop-1yl)-N,N,N-trimethylammonium chloride 
• 1208999-59-0 (2,3-bis(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorooctadecanoyloxy)prop-1-yl)-N,N,N-trimethylammonium chloride 
• 477274-39-8 N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride 
• 75-50-3 trimethylamine 

Relevant articles and documents

Preparation method of positive liposome DOTAP (2,3-dioil oxypropyl trimethylammonium chloride)

The invention discloses a preparation method of positive liposome DOTAP (2,3-dioil oxypropyl trimethylammonium chloride). The preparation method of the positive liposome DOTAP comprises preparation methods of (+/-)-DOTAP, (S)-DOTAP and (R)-DOTAP. The DOTAP product is synthesized by taking cheap 3,-chlorine-1,2-propylene glycol a starting material and by a two-step method, and high-purity positiveliposome DOTAP can be obtained through silica gel column purification. The invention provides a preparation method of the DOTAP, which is low in cost and simple in process. The method is low in raw material cost, mild in reaction condition and simple in aftertreatment, does not need an ion exchange process and has economic property, environmental friendliness and high efficiency.

HFP fluorinated cationic lipids for enhanced lipoplex stability and gene delivery

Although a great number of cationic lipids have been designed and evaluated as gene delivery systems, there is still a need for improvement of nonviral vectors. Recently, cationic lipids incorporating terminal fluoroalkyl segments ( FHP lipids) have been described to display remarkable transfection potency. Here, we describe the synthesis of a new family of fluorinated triblock cationic lipids in which a fluorous segment lays between the cationic and the lipophilic parts of the molecule ( HFP lipids). The compounds were designed so their self-assembly would offer enhanced resistance toward the host's degradation mechanisms mediated by lipophilic insertion. Self-assembly properties of these cationic lipids were evaluated at the air-water interface where they collapse in a highly ordered liquid phase. The HFP lipids efficiently condense DNA, and the resulting lipoplexes display enhanced resistance to amphiphilic agents when compared to nonfluorinated or FHP cationic lipids. Transfection properties of the fluorinated vectors, alone or as mixtures with different helper lipids (DOPE and a fluorinated analogue of DOPE), were then investigated on different cell lines (BHK-21, HepG2, and HeLa) and compared to those of the reference cationic lipid DOTAP. Data show that impermeabilization of the lipidic phase by fluorous segments alter significantly the gene transfection activities. Remarkably, incorporation of DOPE within the lipoplexes provides the particles with high gene transfection activity without reducing their resistance to amphiphilic agents.

Personal care products which include dihydroxypropyltri(C1-C3 alkyl) ammonium salts

A personal care product is provided which includes a composition containing dihydroxypropyltri(C1-C3 alkyl) ammonium salt in a carrier. The composition is packaged for delivery to a consumer and includes instructions printed on or associated with the packaging indicating topical use of the composition on skin, hair or the oral mucosae. Particularly useful is dihydroxypropyltrimonium chloride which operates as a humectant to moisturize both at high and low relative humidity environments.