7365-44-8

Basic information

• Product Name: 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid
• Synonyms: N-[2-HYDROXY-1,1-BIS(HYDROXYMETHYL)ETHYL]TAURINE;N-TRIS(HYDROXYMETHYL)METHYL-2-AMINO-ETHANESULPHONIC ACID;N-TRIS(HYDROXYMETHYL)METHYL-2-AMINOETHANESULFONIC ACID;2-[TRIS(HYDROXYMETHYL)METHYL]-2-AMINOETHANE SULFONIC ACID;2-[TRIS(HYDROXYMETHYL)METHYLAMINO]-1-ETHANESULFONIC ACID;2-[[TRIS(HYDROXYMETHYL)METHYL]AMINO]ETHANESULFONIC ACID;2-([2-HYDROXY-1,1-BIS(HYDROXYMETHYL)ETHYL]AMINO)ETHANESULFONIC ACID;2-[[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]amino]-ethanesulfonicaci
• CAS NO: 7365-44-8
• Molecular Formula: C₆H₁₅NO₆S
• Molecular Weight: 229.25
• EINECS: 230-906-3
• Product Categories: Biochemistry;Good's Buffers;Buffer
• Mol File: 7365-44-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: ~225 °C (dec.)
• Appearance: White/Crystalline Powder
• Density: 1.260 (estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store at RT.
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• PKA: 7.5(at 25℃)
• Water Solubility: SOLUBLE
• Merck: 14,9176
• BRN: 1957061
• CAS DataBase Reference: 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid(7365-44-8)
• EPA Substance Registry System: 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid(7365-44-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 7365-44-8(Hazardous Substances Data)

Usage

Description

2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid, also known as TES, is a structural analog to the Tris buffer and is a commonly used buffering agent in various applications. It is an organic compound with the chemical formula C6H15NO4S. TES is known for its ability to maintain a stable pH in solutions, making it a valuable component in numerous scientific and industrial processes.

Uses

Used in Research and Development:
TES is used as a biological buffer for maintaining a stable pH in various research and development applications. Its buffering capacity helps in preserving the integrity of biological samples and ensuring accurate experimental results.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid is used as a buffering agent in the formulation of drugs and medicines. Its ability to maintain a stable pH in solutions helps in enhancing the stability and efficacy of pharmaceutical products.
Used in Biotechnology:
TES is employed as a buffering agent in biotechnology applications, such as protein purification, enzyme assays, and cell culture. Its buffering capacity ensures that the pH remains stable during these processes, which is crucial for the proper functioning of biological systems.
Used in Diagnostics:
In the diagnostics industry, 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid is used as a component in diagnostic tests and assays. Its buffering properties help maintain the optimal pH conditions required for accurate test results.
Used in Food and Beverage Industry:
TES is utilized as a buffering agent in the food and beverage industry to maintain the pH of various products, ensuring their taste, texture, and shelf life. Its use in this industry is particularly important in the production of acidic or alkaline products, where pH stability is crucial.
Used in Cosmetics and Personal Care Industry:
In the cosmetics and personal care industry, 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid is used as a buffering agent in the formulation of various products, such as skincare, hair care, and oral care products. Its ability to maintain a stable pH helps in preserving the efficacy and stability of these products, ensuring their performance and safety for consumers.

Purification Methods

Crystallise the acid from hot EtOH containing a little water.

InChI:InChI=1/C6H15NO6S/c8-3-6(4-9,5-10)7-1-2-14(11,12)13/h7-10H,1-5H2,(H,11,12,13)

Synthetic route

1-Bromo-2-chloroethane (107-04-0) + 2-amino-2-hydroxymethyl-1,3-propanediol (77-86-1) → N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8)

Conditions	Yield
Stage #1: 1-Bromo-2-chloroethane; 2-amino-2-hydroxymethyl-1,3-propanediol With sodium hydroxide In water for 4h; pH=< 7.0; Reflux; Stage #2: With copper; sodium sulfite In water for 16h; Reflux;	87%

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride (27668-52-6) → disodium 2-[[1-[[3-[dimethyl(octadecyl)ammonio]propyl-[3-hydroxy-2-(hydroxymethyl)-2-(2-sulfoethylamino)propoxy]-[3-hydroxy-2-(hydroxymethyl)-2-(2-sulfonatoethylamino)propoxy]silyl]oxymethyl]-2-hydroxy-1-(hydroxymethyl)ethyl]amino]ethanesulfonate chloride

Conditions	Yield
Stage #1: N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride In N,N-dimethyl-formamide at 145℃; Stage #2: With sodium methylate In N,N-dimethyl-formamide	97%

(Z)-9-octadecenoyl chloride (112-77-6) + N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) → trioleate 2-[tris(oleoyloxymethyl)methylamino]-1-ethanesulfonic acid

Conditions	Yield
In N,N-dimethyl acetamide at 65℃; for 3h; Large scale;	77.8%

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + 1-ethyl-3-methylimidazolium hydroxide → C6H11N2(1+)*C6H14NO6S(1-)

Conditions	Yield
In water at 20℃; for 12h;

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + tetramethyl ammoniumhydroxide (75-59-2) → C4H12N(1+)*C6H14NO6S(1-) (1421259-95-1)

Conditions	Yield
In water at 20℃; for 12h;

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + tetraethylammonium hydroxide (77-98-5) → C8H20N(1+)*C6H14NO6S(1-) (1612259-34-3)

Conditions	Yield
In water at 20℃; for 12h;

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → C16H36N(1+)*C6H14NO6S(1-) (1612259-35-4)

Conditions	Yield
In water at 20℃; for 12h;

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + cholin hydroxide (123-41-1) → cholinium 2-[(2-hydroxy-1,1-bis(hydroxymethyl)ethyl)amino]ethane sulfonate

Conditions	Yield
In aq. buffer for 12h;

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + TPO chloride → C29H35NO8PS(1-)*K(1+)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + (3,5-bis(chloromethyl)-2,4,6-trimethylphenyl)(diphenylphosphoryl)methanone → C36H49N2O14PS2(2-)*2K(1+)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;

N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + TES sodium + octadecyldimethyl[3-(trimethoxysilyl)propyl]ammonium chloride (27668-52-6) → sodium 7,7-bis(3-hydroxy-2-(hydroxymethyl)-2-((2-sulfoethyl)amino)propoxy)-4,4-bis(hydroxymethyl)-11,11-dimethyl-6-oxa-3,11-diaza-7-silanonacosan-11-ium-1-sulfonate chloride

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide at 145℃;

didecylmethyl[3-(trimethoxysilyl)propyl]ammonium chloride + N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (7365-44-8) + TES sodium → N-decyl-N-(3-(7-(3-hydroxy-2-(hydroxymethyl)-2-((2-sulfoethyl)amino)propoxy)-4,4,10,10-tetrakis(hydroxymethyl)-1,14-disulfo-6,8-dioxa-3,11-diaza-7-silatetradecan-7-yl)propyl)-N-methyldecan-1-aminium chloride

Conditions	Yield
In N,N-dimethyl-formamide at 145℃;

Upstream product

• 107-04-0 1-Bromo-2-chloroethane 
• 77-86-1 2-amino-2-hydroxymethyl-1,3-propanediol 

Relevant articles and documents

Preparation method of 2-[[tris(hydroxymethyl)methyl]amino]ethanesulfonic acid

The invention discloses a preparation method of 2-[[tris(hydroxymethyl)methyl]amino]ethanesulfonic acid, which comprises the following steps: dissolving trihydroxymethyl aminomethane and 1,2-dihaloethane in a solvent, heating to reflux reaction while stirring, and controlling the pH value of the solution to be greater than or equal to 7.0 to obtain a first intermediate reaction solution; adding sodium sulfite into the first intermediate reaction solution, and heating to reflux reaction under the action of a catalyst to obtain a second intermediate reaction solution; and cooling and filtering the second intermediate reaction solution, adding cation exchange resin for adsorption, removing the solvent, and crystallizing the liquid to obtain the 2-[[tris(hydroxymethyl)methyl]amino]ethanesulfonic acid. Based on the two-step one-pot method, the reaction yield is high, the post-treatment process is simple and convenient, the product purity is good; meanwhile, the problem of low yield or threewastes caused by use of 2-halogenated ethanesulfonic acid is solved.

Hydrogen ion buffers for biological research.

-