3-((2-Aminoethyl)-dimethylammonio)propane-1-sulfonate
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Product Description
3-((2-Aminoethyl)-dimethylammonio)propane-1-sulfonate is a quaternary ammonium zwitterionic compound featuring a sulfonic acid group and an aminoethyldimethylammonium group. It is highly water-soluble and thermally stable due to its inner salt structure. Unlike the more complex 3-[(3-Cholamidopropyl)dimethylammonio]-1-propanesulfonate, this compound lacks a choline group. It may serve as a biological buffer or surfactant, with potential applications in protein research. However, further experiments are needed to verify its specific functions, such as interactions with G proteins or adenylate cyclase. Synthesis involves reacting a halogenated hydrocarbon with dimethylamine and introducing a sulfonic acid group, while purity can be assessed using chromatographic methods like HPLC.
Synthesis Methods
Preparation: The compound can be prepared analogously to other sulfobetaines by alkylation of a tertiary amine with a sultone. A likely route is the ring-opening reaction of 1,3-propanesultone with N,N-dimethyl-2-aminoethylamine (H₂NCH₂CH₂N(CH₃)₂). In this reaction, the sultone ring opens to attach a 3-sulfopropyl group to the dimethylamino center, yielding the quaternary ammonium sulfonate.
Reagents: 1,3-propanesultone, N,N-dimethylaminoethylamine, solvent, mild heating.
Conditions: No published yields or conditions were found.
Uses
Biochemical Research: Used as a zwitterionic surfactant/detergent (e.g., for protein solubilization).
Protein Separation: Reportedly used as a protein denaturant or separation agent.
Buffer/Catalyst: Mentioned as a component in buffer formulations or as a catalyst in organic synthesis.
Polymer and Biochemical Syntheses: May serve as a monomer or additive in specialty polymer and biochemical syntheses.
Research Chemical: Marketed strictly for non-human, non-therapeutic research purposes (e.g., scientific or industrial applications).
Zwitterionic Polymers: A building block in the synthesis of zwitterionic polymers or surfactants.
Pharmaceutical and Material Science R&D: An intermediate in pharmaceutical or material science research and development.
Properties and Characteristics
Molecular Formula: C₇H₁₈N₂O₃S
Molecular Weight: 210.30 g/mol
Appearance: White to light-yellow solid
Solubility: Highly soluble in water (forms clear aqueous solutions); practically insoluble in nonpolar solvents
pH (aqueous solution): Weakly acidic (consistent with a zwitterion)
pKₐ: Not reported; the tertiary amine is quaternary and non-titratable; the primary amine, if protonated, would have pKₐ ≈9–10 by analogy
Partition Coefficient (Log P): Very low (highly hydrophilic) due to permanent charges
Melting/Boiling Points: No reliable data found; likely decomposes upon strong heating
Structure and Identifiers
IUPAC Name: 3-((2-aminoethyl)dimethylammonio)propane-1-sulfonate
InChI: InChI=1S/C7H18N2O3S/c1-9(2,6-4-8)5-3-7-13(10,11)12/h3-8H2,1-2H3
InChIKey: BTOABBIPPTYPKG-UHFFFAOYSA-N
Canonical SMILES: CN+(CCN)CCCS(=O)(=O)[O-]
Structure Description: The molecule consists of a propane chain with a sulfonate group at one end and a dimethylammonium group attached to the middle carbon, with an additional 2-aminoethyl side chain on the nitrogen. This creates a betaine-like zwitterion structure, similar to those found in some surfactants or biochemical buffers.
Safety
Hazard Classifications: Based on analogous sulfobetaines, it is expected to be a moderate irritant (GHS H315, H319).
Precautions: Avoid inhalation of dust, and avoid contact with skin, eyes, and mucous. In case of contact, rinse thoroughly with water and seek medical attention. Wear appropriate protective gear (gloves, goggles, lab coat) and handle under standard laboratory safety protocols. Store in a cool, dry place in a tightly closed container, and prevent ingestion.
Special Notes: The 1,3-propanesultone precursor is highly toxic and carcinogenic – ensure the absence of sultone in the final material.