2-amino-N-methylethanesulfonamide - ≥95% , CAS No.94987-87-8

CAS: 94987-87-8 Cat. No.: A1073054 Summenformel: C₃H₁₁ClN₂O₂S Molekulargewicht: 174.64 PubChem CID: 46736945

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

CNS(=O)(=O)CCN.Cl

IUPAC Name

2-amino-N-methylethanesulfonamide;hydrochloride

InChIKey

IMDTYQHPAJZVOB-UHFFFAOYSA-N

INCHI

1S/C3H10N2O2S.ClH/c1-5-8(6,7)3-2-4;/h5H,2-4H2,1H3;1H

Isomere SMILES

CNS(=O)(=O)CCN.Cl

PubChem CID

46736945

Molekulargewicht

174.64

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Klasse Organic sulfonic acids and derivatives
      • Subclass Organosulfonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Klasse: Organic sulfonic acids and derivatives
• Subclass: Organosulfonic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Organosulfonamides
• Alternative Parents: Organic sulfonamides Aminosulfonyl compounds Organic oxides Monoalkylamines Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Organosulfonic acid amide - Organic sulfonic acid amide - Aminosulfonyl compound - Sulfonyl - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Hydrochloride - Primary amine - Organosulfur compound - Organonitrogen compound - Primary aliphatic amine - Amine - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as organosulfonamides. These are compounds containing the sulfonamide functional group, an amide of sulfonic acid with the general structure R1S(=O)2N(R2)R3 (R1=alkyl, aryl; R2,R3=H, alkyl, aryl).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 138.190 g/mol
• XLogP3: -1.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 138.046 Da
• Monoisotopic Mass: 138.046 Da
• Topological Polar Surface Area: 80.600 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 134.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

• Not applicable to this product type. No validated protocols such as WB, IHC, IF, or FC are associated with this small-molecule reagent.
• General guidance
  • For solution preparation, weigh accurately (drying if necessary), dissolve in an appropriate solvent (water, buffer, DMSO), and filter if particle-free solutions are required.
  • For conjugation/synthesis, see Reaction Conditions and Synthetic Utility sections for starting points and adjust to your system.

Biological Roles

• Item-specific biological role claims

  • None provided. Research Use Note: For research use only.

• General context (no clinical claims)

  • 2-amino-N-methylethanesulfonamide is a small, highly polar organic molecule. It is not a known endogenous metabolite. Sulfonamides are commonly used as bioisosteres of carboxylic acids or sulfates in medicinal chemistry to modulate solubility, acidity/basicity, and binding interactions.
  • The primary amine can be protonated at physiological pH ranges depending on microenvironment, potentially enabling ionic interactions in bioconjugates. The sulfonamide N–H can act as a hydrogen-bond donor; the sulfonyl oxygens are acceptors, influencing binding when incorporated into ligands.

• Use in life-science research (general)

  • Can serve as a polar linker or spacer between biological recognition motifs and reporter groups, improving water compatibility of conjugates.
  • May be used to explore structure–property relationships when comparing amide vs sulfonamide linkers in biomolecular constructs.

• Note

  • No specific biological activity or pathway engagement is asserted for this item. Any biochemistry use should be validated empirically in the intended assay system.

Buffer Applications

• Applicability

  • This compound is not a standardized Good’s buffer or a commonly referenced buffering agent with an established pKa/pH operating range. Therefore, it is not typically used as a primary buffer component.

• Exploratory use (general, literature-based rationale)

  • Given the presence of a primary amine (conjugate acid pKa for similar aliphatic amines ~9–10), solutions may exhibit limited buffering capacity in the alkaline range if the amine is the dominant acid–base site. The sulfonamide N–H is weakly acidic (for related alkylsulfonamides ~pKa 9–11), but practical buffering windows and ionic strengths for this exact compound are not established here.

• Practical guidance

  • If investigating as an auxiliary buffer component, empirically determine pKa and buffering range by titration in your matrix (ionic strength, temperature, and cosolvent strongly affect results).
  • Established alternatives: For pH control, consider validated buffers (HEPES, MOPS, TAPS, Tris, MES) with well-documented properties.

• Item-specific data

  • Buffer recipes, pKa, and ionic strength parameters: Not specified for this item; refer to CoA/Spec Sheet or determine experimentally.

Green Alternatives

• Context

  • This compound is a reagent/building block rather than a solvent. Green considerations focus on solvent and reagent choices in reactions employing this compound.

• Greener choices for common operations (literature/general)

  • Amidation/coupling: Use water or water-ethanol mixtures with water-tolerant coupling systems (e.g., EDC with NHS) instead of DMF/DCE where feasible.
  • N-alkylation: Replace DMF with MeCN or 2-MeTHF when solubility allows; consider phase-transfer catalysis in aqueous media to minimize dipolar aprotics.
  • Workup: Favor aqueous extractions with eco-friendlier solvents (EtOAc, MTBE) over chlorinated solvents.

• Comparison snapshot (general)

  • DMF/DMSO: excellent solvency; high EHS burden; difficult removal.
  • MeCN/2-MeTHF/EtOH/H2O: improved green metrics; may require optimization for rates/solubility.

• Waste and exposure reduction

  • Use stoichiometric balance to minimize excess coupling reagents.
  • Choose catalytic or reagent-lite activations (e.g., CDI, T3P with efficient quench) and avoid azabenzotriazole additives when not essential.

Pharmaceutical Uses

• Item-specific status

  • No pharmacopeial grade or excipient designation is provided. Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• General roles (no therapeutic claims)

  • As a polar building block, 2-amino-N-methylethanesulfonamide may be used in discovery and process research to introduce sulfonamide motifs or cationic handles into candidate molecules.
  • The sulfonamide functionality is a common pharmacophore/bioisostere in medicinal chemistry, often leveraged to tune solubility and hydrogen-bonding.

• Formulation relevance (general)

  • Not recognized as a standard excipient. If contemplated for enabling formulations (e.g., salt formation with acids at the amine), full preformulation work (pKa, hygroscopicity, compatibility, stability) is required.

• Compliance note

  • This material is supplied for research use only. It is not intended for human or veterinary use, and no clinical suitability is implied.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed values for the named structure (not item specifications)

  • Physical state: typically an off-white to white crystalline solid for related simple aliphatic sulfonamides (literature trend).
  • Aqueous behavior: multiple hydrogen-bond donors/acceptors suggest high hydrophilicity and likely good water solubility; actual solubility for this specific item is not specified.
  • Acid–base properties: aliphatic primary amine conjugate acid pKa typically ~9–10 (literature, general); secondary alkylsulfonamide N–H pKa often in the ~9–11 range (literature, scaffold-dependent). Specific pKa values for 2-amino-N-methylethanesulfonamide are not established here.
  • LogP: expected to be very low (high polarity) for similar aminosulfonamides; specific value not available.
  • Melting point, boiling point, density, refractive index: Not located in standard references for this exact compound during preparation; Not specified for this item; refer to CoA/Spec Sheet.

• Practical handling implications (general)

  • Hygroscopicity: polar sulfonamide/amine salts can be moisture-attractive; monitor mass if preparing solutions gravimetrically. Item-specific hygroscopicity is not specified.
  • Solution preparation: dissolves readily in polar protic/aqueous media and in highly polar aprotic solvents (DMF, DMSO) for related compounds; verify experimentally for this item.

Quality and Grades

• Item-specific quality information (from Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on grades (general; not item-specific claims)

  • Research grade: Suitable for most synthetic and biochemical laboratory applications. CoA typically provides purity by HPLC/GC/NMR and residual solvent/water where applicable.
  • High-purity/low-residue grades: When performing sensitive transformations (e.g., peptide couplings or pharmaceutical impurity studies), consider lots with tight specifications on water, residual solvents, and metal content. For this item, exact limits are Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers: None indicated in Product Data. If stabilizers are used in any lot, they will be disclosed on the CoA and may influence reactivity of the amine or sulfonamide functionalities.

• Verification

  • Request and review the CoA/Spec Sheet for: assay method and result, identification (NMR/IR/LC-MS), residual water (e.g., KF), and any inorganic/organic impurities relevant to your application.

Reaction and Applications

• Functional handles

  • Primary amine: nucleophilic; engages in acylation (amides/ureas/carbamates), sulfonylation (to sulfamides), reductive amination, and conjugation to activated esters (NHS, pentafluorophenyl esters).
  • Secondary sulfonamide (N-methyl): N–H acidity enables deprotonation and subsequent N-alkylation or N-acylation; sulfonyl group confers strong electron-withdrawing character and H-bonding capability.

• Representative application spaces (literature/general)

  • Linker/scaffold in medicinal and chemical biology programs where a cationic handle (amine) is desired orthogonal to a sulfonamide motif (bioisosteric to carbonyl derivatives).
  • Preparation of zwitterionic or highly water-soluble conjugates by appending sulfonamide-bearing tethers to dyes, labels, or polymer backbones.
  • Formation of bifunctional reagents: amide formation at the primary amine, followed by selective modification at the sulfonamide N under stronger/basic conditions.

• Practical tips

  • Protecting groups: The primary amine can be protected (Boc, Fmoc, Cbz) to enable selective sulfonamide N-functionalization; the sulfonamide N–H can be transiently masked (e.g., as N-alkyl) if selective amine derivatization is needed.
  • Coupling reagents: EDC/HOBt, HATU, PyBOP, T3P, or acid chlorides for rapid amidation; monitor for overacylation if the sulfonamide is deprotonated.
  • Chemoselectivity: At mild base, the primary amine reacts preferentially with activated acyl donors; strong base (NaH, K2CO3) can activate the sulfonamide N for N-alkylation.

• Manufacturer Applications

  • Product Data list no specific applications. Typical laboratory uses include building-block chemistry and conjugation workflows in life-science research. Always validate in your system of interest.

Reaction Conditions

• General conditions (illustrative; literature-based; not specifications)

  • Amide formation at the primary amine: HATU or EDC/NHS in DMF, MeCN, or mixed aqueous media; base DIPEA/TEA (1.5–3.0 equiv); 0–25 C; 0.5–16 h. Monitor for overacylation if sulfonamide is deprotonated.
  • Urea/carbamate formation: CDI in THF/DMF at 0–25 C; or reaction with isocyanates/chloroformates in DCM/DMF with base (TEA).
  • Sulfonamide N-alkylation: K2CO3 or Cs2CO3 (2–3 equiv) in DMF or MeCN, 20–60 C, 2–18 h; for less reactive electrophiles, NaH (0.5–1.0 equiv) at 0–25 C may be used with caution.
  • Reductive amination at the primary amine: aldehyde/ketone (1.1–2.0 equiv), NaBH3CN (1.2–2.0 equiv) in MeOH/AcOH or MeOH/THF, 0–25 C, 1–6 h.

• Solvent alternatives and green tweaks

  • Where solubility allows, MeCN or EtOH/H2O can replace DMF; 2-MeTHF may substitute for THF/DCM in some acylations. Microwave or flow can reduce time and solvent volumes.

• Workup/purification

  • Due to high polarity, products may partition into aqueous layers; adjust pH to move amine-containing species. Reverse-phase chromatography or ion-exchange can be advantageous for very polar derivatives.

• Expected outcomes

  • Yields are strongly substrate/electrophile dependent; for simple acylations and reductive aminations of primary aliphatic amines, literature often reports moderate to high yields (60–90%) under optimized conditions; actual results must be determined experimentally.

Safety and Handling

• Item-specific hazard information (from Product Data)

  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety guidance for aminosulfonamides (literature; not item-specific classification)

  • Hazards: May cause irritation to skin, eyes, and respiratory tract upon contact with dusts or solutions, as is common with small polar amines/sulfonamides.
  • PPE: Use lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to minimize dust inhalation.
  • Storage incompatibilities: Keep separate from strong oxidizers and strong acids/bases that could cause decomposition or exotherm upon neutralization. Avoid isocyanates and acid chlorides unless intentionally reacting.
  • First-aid overview: Inhalation—move to fresh air; Skin—wash with soap and water; Eyes—rinse with water for several minutes; Ingestion—rinse mouth and seek medical advice. Follow site SOPs.
  • Spill/cleanup: Avoid dust formation; sweep or vacuum with HEPA and dispose per local regulations.

• Authoritative source

  • Always consult the product’s SDS for definitive hazard classification, exposure limits, and response procedures.

Solvent Selection

• Polarity class and miscibility (general expectations for aminosulfonamides; verify experimentally)

  • Highly polar; expected to be freely soluble in water and polar protic solvents (water, methanol, ethanol) and in polar aprotic media (DMSO, DMF). Limited solubility likely in nonpolar solvents (hexanes, toluene).
  • For aqueous work, adjust pH to protonate the amine (acidic) or deprotonate the sulfonamide (basic) to optimize solubility, being mindful of potential hydrolysis/side reactions under strong conditions.

• Choosing solvents by task

  • Stock solutions for bioassays: water or buffer, or DMSO for concentrated stocks; filter-sterilize if needed.
  • Coupling/derivatization at the primary amine: anhydrous DMF, DCM/DMF mixtures, or MeCN with organic bases (e.g., DIPEA) are common.
  • N-alkylation/acylation at the sulfonamide: polar aprotic solvents (DMF, DMSO) with strong bases or phase-transfer conditions.

• Small comparison (general)

  • Water: green, excellent for ionizable substrates; may require pH control.
  • MeOH/EtOH: good solvency; easier removal than DMF/DMSO.
  • DMSO/DMF: maximal solvency; consider downstream removal and toxicity profiles.

• Note

  • Item-specific solubility data are Not specified for this item; refer to CoA/Spec Sheet. Conduct a small-scale solubility screen when planning new procedures.

Storage and Reconstitution

• Item-specific storage (from Product Data)

  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance (small polar aminosulfonamides)

  • Keep container tightly closed in a dry, well-ventilated area. Protect from excessive moisture and strong light. If long-term storage is planned, consider desiccation to maintain constant mass.
  • Segregate from strong oxidizers and corrosives. Use clean, dry tools to avoid contamination.

• Reconstitution and solution handling

  • Solvents: Water, buffer, MeOH/EtOH, DMSO, or DMF depending on application; confirm solubility at desired concentration.
  • Filtration: If needed, 0.2 µm PTFE/nylon filters are typically compatible with aqueous/organic solutions.
  • Storage of solutions: Aqueous solutions are best prepared fresh. If storage is necessary, refrigerate (2–8 C) and assess stability by analytical methods (e.g., HPLC) prior to use. Avoid repeated freeze–thaw cycles by aliquoting.

• Specifications note

  • Any item-specific stability limits, water content, or impurity thresholds are Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Brief description: 2-amino-N-methylethanesulfonamide is a small, bifunctional organic molecule bearing a primary amine and a secondary sulfonamide (N-methyl) connected through an ethylene linker.

• Item-specific (from Product Data)

  • Product name: 2-amino-N-methylethanesulfonamide (SKU: A1073054)
  • CAS: 94987-87-8
  • InChIKey: 144605 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature (general reference for this structure; not item specifications)

  • Putative molecular formula (by structure reasoning): C3H10N2O2S
  • Approximate formula weight: ~138.19 g/mol (computed)
  • Representative SMILES: NCCS(=O)(=O)N(C) (literature representation of the named structure)
  • Functional groups: primary amine (–CH2–CH2–NH2), secondary sulfonamide (–SO2–NH–CH3)
  • Structural features: a two-carbon linker (ethylene) connects a terminal –NH2 to a sulfonyl group; the sulfonyl nitrogen bears a methyl substituent. No rings, no stereocenters. The molecule is highly polar and capable of multiple hydrogen-bonding interactions (donor and acceptor).

• General chemistry notes

  • The basic amine can be protonated (forming an ammonium), while the sulfonamide N–H is comparatively acidic for an amide-type N–H, enabling selective functionalization under appropriate conditions.

Synthetic Utility

• Orthogonal reactivity

  • Primary amine: readily forms amides (acid chlorides, activated esters, carbodiimide couplings), ureas (via CDI or isocyanates), carbamates (chloroformates), and can undergo reductive amination with aldehydes/ketones.
  • Secondary sulfonamide (N–H): deprotonation (e.g., NaH, K2CO3 with phase-transfer) enables N-alkylation; acylation affords N-acylsulfonamides; sulfonamide can also participate in H-bond networks that modulate binding or material properties.

• Selectivity strategies

  • Protect the primary amine (Boc/Fmoc) to enable selective sulfonamide derivatization; conversely, transiently mask the sulfonamide N by N-alkylation or via chemoselective acylation conditions that favor the more nucleophilic amine.
  • Exploit differential basicity: amine engages electrophiles under mild base; sulfonamide needs stronger base or more reactive electrophiles.

• Retrosynthetic value

  • Serves as a short ethylene spacer terminating in an aminosulfonamide; useful for assembling sulfamide-like linkages or for installing sulfonamide motifs distal to a primary amine for conjugation.

• Representative transformations (literature/general)

  • Amide coupling in DMF/DIPEA at 0–25 C to give amide-linked conjugates.
  • N-alkylation of the sulfonamide in DMF or MeCN with alkyl halides under K2CO3/phase-transfer conditions.
  • Reductive amination of the terminal amine (NaBH3CN or BH(OAc)3) in MeOH/AcOH followed by optional acylation of the sulfonamide.

Target Specificity

• Not applicable to this product type. This item is a small-molecule reagent/building block, not an antibody, enzyme, or targeted biologic. No antigen/epitope, species reactivity, clone, or isotype information applies.