4432-31-9

Basic information

• Product Name: 4-Morpholineethanesulfonic acid
• Synonyms: 4-Morpholinoethanesulfonic acid; mes free acid molecular biology; mes free acid plant cell culture tested; 2-(4-Morpholino)ethanesulphonic acid; MES 2-(N-Morpholino)ethanesulfonic acid; MES, Free Acid; TIMTEC-BB SBB009135; MORPHOLINOETHANE SULFONIC ACID; mes(bufferingagent); morpholinoethanesulfonic; MES BUFFERED SALINE; 2-(N-MORPHOLINO)ETHANESULFONIC ACID; 2-(N-MORPHOLINO)ETHANESULPHONIC ACID; 2-(morpholin-4-yl)ethanesulfonic acid; 1-morpholin-4-ylethanesulfonic acid; 2-(4-Morpholino) ethane sulfonic acid; MES; 2-Morpholinoethanesulfonic Acid
• CAS NO: 4432-31-9
• Molecular Formula: C₆H₁₃NO₄S
• Molecular Weight: 195.2367
• EINECS: 224-632-3
• Product Categories: buffer;Pharmaceutical Raw Materials;Biochemistry;Good's Buffers;Biotechnology Performance Certified (BPC) BuffersBiological Buffers;Buffer Convenience Packaging;Buffer SolutionsBiological Buffers;Buffers A to ZBiological Buffers;Good Buffers;BioUltraBiological Buffers;Buffer SolutionsProtein Structural Analysis;AlphabeticalMolecular Biology;Biological Buffers;BioUltra Buffers;Molecular Biology Reagents;Optimization Reagents;X-Ray Crystallography
• Mol File: 4432-31-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 243℃
• Boiling Point: 102°C
• Density: 1.368g/cm³
• Refractive Index: 1.525
• Storage Temp.: Store at RT.
• Solubility: H2O: 0.5?M at?20?°C, clear
• PKA: pKa at 0.1M ionic: 0°, 6.38; 20°, 6.15; 37°, 5.98; pKa1 1.99; pKa2 6.21; pKa/°C -0.011
• Water Solubility: 185.2g/L at 20℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 13,5929
• BRN: 6350956
• CAS DataBase Reference: 4-Morpholineethanesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Morpholineethanesulfonic acid(4432-31-9)
• EPA Substance Registry System: 4-Morpholineethanesulfonic acid(4432-31-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: S22:; S24/25:
• WGK Germany: 1
• RTECS: QE9104530
• Hazardous Substances Data: 4432-31-9(Hazardous Substances Data)

Usage

Application

4-Morpholineethanesulfonic acid (MES) is one of the good′s buffers, and the most extensively application is biological buffers. MES is a zwitterionic N-substituted aminosulfonic acid with a morpholinic ring and it does not form complexes with the majority of the metals used in environmental and biological studies. It is easily soluble in water and has minimum lipid solubility, making it impermeable to membranes. MES has been also used as a component of the elution buffer used to elute plasma from α2-macroglobulin affinity column. It has been used as an activation buffer during antibody conjugation to microparticles and it has been used in the functionalization of microchannels during the creation of microfluidic-integrated surface plasmon resonance (SPR) platform for pathogen detection.

Chemical Properties

White/clear crystalline powder

Uses

Different sources of media describe the Uses of 4432-31-9 differently. You can refer to the following data:
1. Biological buffer.
2. MES solution has been used to activate microspheres. It has also been used as a component of activating solution to activate carboxyl groups of poly lactic-co-glycolic acid (PLGA).

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise MES from hot EtOH containing a little water. The picrate crystallises from EtOH and has m 178.8-182o. [Malkiel & Mason J Org Chem 8 199 1943, Beilstein 27 III/IV 370.]

Synthetic route

morpholine (110-91-8) + sodium vinylsulfonate (3039-83-6) → 4-morpholineethanesulfonic acid (4432-31-9)

Conditions	Yield
In water at 60℃; for 6h; Large scale;	85%

2-morpholin-4-yl-ethanesulfonic acid 4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutyl ester → 4-morpholineethanesulfonic acid (4432-31-9)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 48h;	72%

N-(2-chlorethyl)morpholine (3240-94-6) → 4-morpholineethanesulfonic acid (4432-31-9)

Conditions	Yield
With water; sodium sulfite

4-morpholineethanesulfonic acid (4432-31-9) + 1,1'-(1,4-butanediyl)bis(2-ethylbenzimidazole) (1059536-95-6) + water (7732-18-5) + silver carbonate → [Ag(1,1'-(1,4-butanediyl)bis(2-ethylbenzimidazole))0.5(2-(N-morpholino)ethanesulfonate)]*H2O

Conditions	Yield
In ethanol; ammonia aq. NH3; Ag compd., acid, and ligand (1:2:1 molar ratio) in EtOH, stirred for 30 min, dissolved (aq. ammonia); crystd. on storage at room temp., elem. anal.;	68%

4-morpholineethanesulfonic acid (4432-31-9) + 1,1′-(1,4-butanediyl)bis(2-methylbenzimidazole) (1059536-93-4) + silver carbonate → [Ag(1,1'-(1,4-butanediyl)bis(2-methylbenzimidazole))0.5(2-(N-morpholino)ethanesulfonate)]

Conditions	Yield
In ethanol; ammonia aq. NH3; Ag compd., acid, and ligand (1:2:1 molar ratio) in EtOH, stirred for 30 min, dissolved (aq. ammonia); crystd. on storage at room temp., elem. anal.;	66%

4-morpholineethanesulfonic acid (4432-31-9) → morpholine (110-91-8) + 2-oxo-ethanesulfonic acid (32797-12-9)

Conditions	Yield
With (batho)2CuII (batho = 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolinedisulfonate); water at 25℃; for 24h; Rate constant; pH 8;

benzo[c][1,2,5]thiadiazole-4,7-dicarbonitrile (20138-79-8) + 4-morpholineethanesulfonic acid (4432-31-9) → C8H2N4S(1-) + C6H12NO4S*H(1+)

Conditions	Yield
With cetyltrimethylammonim bromide In water Mechanism; Irradiation; electron transfer in presence of micelles or bilayers;

4-morpholineethanesulfonic acid (4432-31-9) + sodium anthraquinone-1,5-disulphonate (853-35-0) → C14H8O8S2(2-)*2Na(1+)

Conditions	Yield
With benzo[c][1,2,5]thiadiazole-4,7-dicarbonitrile; cetyltrimethylammonim bromide In water for 2.5h; Mechanism; Irradiation;
With benzo[c][1,2,5]thiadiazole-4,7-dicarbonitrile; dimethyldioctadecylammonium bromide In water for 2.5h; Mechanism; Irradiation;

4-morpholineethanesulfonic acid (4432-31-9) → 2-morpholinoethanesulfonyl chloride (103654-84-8)

Conditions	Yield
With oxalyl dichloride In dichloromethane at 0℃;

4-morpholineethanesulfonic acid (4432-31-9) → 2-[1-(3,4-dichlorophenyl)-1H-pyrazol-3-yloxy]ethyl 2-morpholinoethanesulfonate

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 0 °C 2: triethylamine / dichloromethane / 18 h / 20 °C View Scheme

4-morpholineethanesulfonic acid (4432-31-9) + 1-ethyl-3-methylimidazolium hydroxide → C6H11N2(1+)*C6H12NO4S(1-) (1393375-77-3)

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

4-morpholineethanesulfonic acid (4432-31-9) + tetramethyl ammoniumhydroxide (75-59-2) → C4H12N(1+)*C6H12NO4S(1-) (1612259-38-7)

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

4-morpholineethanesulfonic acid (4432-31-9) + tetraethylammonium hydroxide (77-98-5) → C8H20N(1+)*C6H12NO4S(1-) (1612259-39-8)

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

4-morpholineethanesulfonic acid (4432-31-9) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → 2-Morpholin-4-yl-ethanesulfonatetetrabutyl-ammonium; (113598-98-4)

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

4-morpholineethanesulfonic acid (4432-31-9) + cholin hydroxide (123-41-1) → cholinium 2-(N-morpholino)ethanesulfonate

Conditions	Yield
In aq. buffer for 12h;

4-morpholineethanesulfonic acid (4432-31-9) → 2-(morpholin-4-yl)ethane-1-sulfonyl chloride hydrochloric acid salt

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 75℃; for 3h;	1.57 g

Upstream product

• 110-91-8 morpholine 
• 3039-83-6 sodium vinylsulfonate 
• 3240-94-6 N-(2-chlorethyl)morpholine 

Downstream Products

• 110-91-8 morpholine 
• 32797-12-9 2-oxo-ethanesulfonic acid 

Relevant articles and documents

Synthetic method of biological buffer agent--morpholineethanesulfonic acid

The invention belongs to the field of organic synthesis and specifically relates to a synthetic method of a biological buffer agent--morpholineethanesulfonic acid. In the method, self-made SVS can beused to avoid harmful impurities from being mixed in the final product. In the method, SVS and morpholine are adopted to synthesize MES-Na. The process is simple and environmentally-friendly, and no foreign matter is generated. According to the method, acidic ion exchange resin is adopted for acidification to remove impurity cation, thus achieving the purification purpose. General decoloration, crystallization, centrifugation and drying processes are used in the method, and the production is easy to implement. In the production process, oxidative deterioration of the materials is avoided through temperature control and nitrogen protection, thereby producing the high-quality biological buffer agent MES. The prepared product is easy to separate, and the method is convenient to operate and has high practicality.

A new strategy for the synthesis of taurine derivatives using the 'safety-catch' principle for the protection of sulfonic acids

The safety-catch principle has been applied for the development of a new method for protecting sulfonic acids. 2,2-Dimethylsuccinic acid was reduced to 2,2-dimethylbutane-1,4-diol, which was selectively silylated to give 4-(tert-butyldiphenylsilanyloxy)-2,2-dimethylbutan-1-ol. Reaction of the latter compound with 2-chloroethanesulfonyl chloride in the presence of triethylamine afforded 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutyl ethenesulfonate directly. The ethenesulfonate underwent Michael-type addition with secondary amines to give protected derivatives of taurine (2-aminoethanesulfonic acid). Deprotection was achieved on treatment with tetrabutylammonium fluoride, whereby cleavage of the silicon-oxygen bond led to an intermediate alkoxide that immediately cyclised to 2,2-dimethyltetrahydrofuran with liberation of a sulfonate. Pure sulfonic acids were obtained from the crude product by ion exchange chromatography on a strongly basic resin, which was eluted with aqueous acetic acid. The method developed should be generally applicable to the protection of sulfonic acids and is amenable to a multiparallel format. This journal is The Royal Society of Chemistry.

Zwitterionic compounds and their n-halo derivatives for use in the treatment of clinical conditions

Zwitterionic compounds selected from: taurine (2-aminoethanesulphonic acid), 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido)iminodiacetic acid (ADA), piperazine-N,N'bis(2-ethanesulphonic acid (PIPES), N-(2-acetamido)-2-aminoethanesulphonic acid (ACES), N,N-bis(2-hydroxyethyl)-2-aminoethanesulphonic acid (BES), 3-(N-morpholino)propanesulphonic (MOPS), N-N[tris(hydroxymethyl)-methyl]-2-aminoethanesulphonic acid (TES), N-2-hydroxyethylpiperazine-N'-2-ethanesulphonic acid (HEPES), N-2-hydroxyethylpiperazine-N'3-propanesulphonic acid (H)EPPS), 2-(cyclohexylamino)ethanesulphonic acid (CHES) or 3-(cyclohexylamino)propanesulphonic acid (CAPS), and their N-halo derivatives can be used separately or in combination in the treatment of related clinical conditions by stimulating myeloperoxidase activity, which in turn stimulates hypochlorous acid production in vivo, which leads inter alia to enhanced leukotriene inactivation.