103-47-9

Basic information

• Product Name: N-Cyclohexyltaurine
• Synonyms: N-Cyclohexyl-2-aminoethanesulfonic acid;n-cyclohexyltaurine;2-(CYCLOHEXYLAMINO)ETHANE SULPHONIC ACID;2-(N-CYCLOHEXYLAMINO)ETHANESULFONIC ACID;2-(N-CYCLOHEXYLAMINO)ETHANESULPHONIC ACID;CYCLOHEXYLAMINOETHANESULFONIC ACID;CHES;LABOTEST-BB LT01147803
• CAS NO: 103-47-9
• Molecular Formula: C₈H₁₇NO₃S
• Molecular Weight: 207.29
• EINECS: 203-115-6
• Product Categories: Pharmaceutical Intermediates;Buffer;Pyridines ,Halogenated Heterocycles
• Mol File: 103-47-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: ≥300 °C
• Appearance: White/Solid
• Density: 1.2045 (rough estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.5364 (estimate)
• Storage Temp.: Store at RT.
• Solubility: H2O: 0.5 M at 20 °C, clear, colorless
• PKA: 9.3(at 25℃)
• Water Solubility: Soluble
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,2055
• BRN: 2967601
• CAS DataBase Reference: N-Cyclohexyltaurine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cyclohexyltaurine(103-47-9)
• EPA Substance Registry System: N-Cyclohexyltaurine(103-47-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36-20/22
• Safety Statements: 26-28-24/25-16-60
• WGK Germany: 3
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 103-47-9(Hazardous Substances Data)

Usage

Chemical Properties

White/clear cryst. powder

Uses

Different sources of media describe the Uses of 103-47-9 differently. You can refer to the following data:
1. Biological buffer.
2. CHES is zwitterionic buffer useful in pH range 8.6 to 10.0.CHES is widely utilized as a buffer which is used for investigations on pH-dependent processes in enzymology. It has been shown to have an unusually high affinity for the iodoacetate binding site of liver alcohol dehydrogenase.
3. 2-(Cyclohexylamino)ethanesulfonic acid (CHES) has been used in the preparation of dimethyl trisulfide- polysorbate 80 (DMTS-PS80) formulation.

General Description

CHES (2-(N-cyclohexylamino)ethanesulphonic acid) is regarded as Good′s buffers for its self-buffering and biocompatible feature. It is used in protein stabilization and does not interact with metals.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H17NO3S/c10-13(11,12)7-6-9-8-4-2-1-3-5-8/h8-9H,1-7H2,(H,10,11,12)

Synthetic route

cyclohexylamine (108-91-8) + 1,2-dichloro-ethane (107-06-2) → 2-(cyclohexylamino)ethanesulfonic acid (103-47-9)

Conditions	Yield
Stage #1: cyclohexylamine With copper; sodium sulfite In ethanol; water Reflux; Stage #2: 1,2-dichloro-ethane In ethanol; water at 65℃; for 3h;	86%

ethene-sulfonate d'isopropyle (3851-91-0) + cyclohexylamine (108-91-8) + 2) HCl → 2-(cyclohexylamino)ethanesulfonic acid (103-47-9)

Conditions	Yield
1) MeOH, 0 deg C; 2) 10 deg C; 70 deg C, 18 h; Yield given. Multistep reaction;

cyclohexylamine (108-91-8) + Na-salt of 2-chloroethane-1-sulfonic acid (15484-44-3) → 2-(cyclohexylamino)ethanesulfonic acid (103-47-9)

Conditions	Yield
In water at 50℃; for 6h; Reflux;	10.9 g

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) → 2-cyclohexyl-1,2-thiazetidine 1,1-dioxide (85582-50-9)

Conditions	Yield
	76%
With phosphorus pentachloride; ammonia; water; trichlorophosphate 1.) 60 deg C, 2.) CHCl3, 10-15 deg C, 24 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 65 percent / PCl5, POCl3 / 90 °C 2: 94 percent / Na2CO3 / ethyl acetate / 48 h / 110 °C View Scheme

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) → 2-Cyclohexylamino-ethanesulfonyl chloride; hydrochloride (103020-61-7)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate at 90℃;	65%

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) → (E)-4-(α-aminobenzylidene)-2-cyclohexyl-1,2-thiazetidine 1,1-dioxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent 2: 1.) n-BuLi / 1.) THF, -78 deg C, 45 sec, 2.) THF, 30 min View Scheme

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) → (E)-4-(α-amino-4-chlorobenzylidene)-2-cyclohexyl-1,2-thiazetidine 1,1-dioxide (148588-19-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent 2: 1.) n-BuLi / 1.) THF, -78 deg C, 45 sec, 2.) THF, 30 min View Scheme

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) → (E)-4-(α-acetamido-4-chlorobenzylidene)-2-cyclohexyl-1,2-thiazetidine 1,1-dioxide

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent 2: 1.) n-BuLi / 1.) THF, -78 deg C, 45 sec, 2.) THF, 30 min 3: 23 percent / pyridine / diethyl ether / 1.) 15 min, cooling, 2.) RT, 14 h View Scheme

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) → (E)-2-cyclohexyl-4-(α-phenylacetamido-4-chlorobenzylidene)-1,2-thiazetidine 1,1-dioxide

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent 2: 1.) n-BuLi / 1.) THF, -78 deg C, 45 sec, 2.) THF, 30 min 3: 27 percent / pyridine / diethyl ether / 1.) 15 min, cooling, 2.) RT, 14 h View Scheme

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) → (E)-2-cyclohexyl-4-(α-phenoxyacetamido-4-chlorobenzylidene)-1,2-thiazetidine 1,1-dioxide

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent 2: 1.) n-BuLi / 1.) THF, -78 deg C, 45 sec, 2.) THF, 30 min 3: 43 percent / pyridine / diethyl ether / 1.) 15 min, cooling, 2.) RT, 14 h View Scheme

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) + 1-ethyl-3-methylimidazolium hydroxide → C6H11N2(1+)*C8H16NO3S(1-) (1612259-41-2)

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

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) + tetramethyl ammoniumhydroxide (75-59-2) → C4H12N(1+)*C8H16NO3S(1-) (122732-69-8)

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

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) + tetraethylammonium hydroxide (77-98-5) → C8H20N(1+)*C8H16NO3S(1-) (122732-70-1)

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

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → 2-Cyclohexylamino-ethanesulfonatetetrabutyl-ammonium; (113599-04-5)

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

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) + cholin hydroxide (123-41-1) → cholinium 2-(cyclohexylamino)ethanesulfonate

Conditions	Yield
In aq. buffer for 12h;

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) + TPO chloride → C31H37NO5PS(1-)*K(1+)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;

2-(cyclohexylamino)ethanesulfonic acid (103-47-9) + (3,5-bis(chloromethyl)-2,4,6-trimethylphenyl)(diphenylphosphoryl)methanone → C40H53N2O8PS2(2-)*2K(1+)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;

Upstream product

• 3851-91-0 ethene-sulfonate d'isopropyle 
• 108-91-8 cyclohexylamine 
• 15484-44-3 Na-salt of 2-chloroethane-1-sulfonic acid 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 113599-04-5 2-Cyclohexylamino-ethanesulfonatetetrabutyl-ammonium; 
• 122732-70-1 C₈H₂₀N⁽¹⁺⁾*C₈H₁₆NO₃S^(1-) 
• 122732-69-8 C₄H₁₂N⁽¹⁺⁾*C₈H₁₆NO₃S^(1-) 
• 1612259-41-2 C₆H₁₁N₂⁽¹⁺⁾*C₈H₁₆NO₃S^(1-) 
• 148588-19-6 (E)-4-(α-amino-4-chlorobenzylidene)-2-cyclohexyl-1,2-thiazetidine 1,1-dioxide 
• 85582-50-9 2-cyclohexyl-1,2-thiazetidine 1,1-dioxide 

Relevant articles and documents

Preparation method of N-cyclohexyl-2-aminoethanesulfonic acid

The invention discloses a preparation method of N-cyclohexyl-2-aminoethanesulfonic acid, which comprises the following steps: heating cyclohexylamine, 1,2-dichloroethane and sodium sulfite to reflux in the presence of a solvent and a catalyst, reacting at reflux temperature, filtering the reaction solution after the reaction is finished, and acidifying and crystallizing the liquid to obtain the N-cyclohexyl-2-aminoethanesulfonic acid. According to the invention, with the cyclohexylamine, 1,2-dichloroethane and sodium sulfite as raw materials, the product can be prepared just through a one-potone-step process; therefore, the reaction conditions are mild, operation is easy, mastering is easy, products obtained after reaction are easy to treat, and the purity of the products is high and canreach 99% or above.

Isolation of nucleic acids

A method for extracting nucleic acids from a biological material such as blood comprises contacting the mixture with a material at a pH such that the material is positively charged and will bind negatively charged nucleic acids and then eluting the nucleic acids at a pH when the said materials possess a neutral or negative charge to release the nucleic acids. The nucleic acids can be removed under mildly alkaline conditions to the maintain integrity of the nucleic acids and to allow retrieval of the nucleic acids in reagents that are immediately compatible with either storage or analytical testing.

Use of zwitterionic compounds and their N-halo derivatives

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 aliato enhanced leukotriene inactivation.