This compound belongs to the class of organic compounds known as n-methylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries a methyl group.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
114.190 g/mol
XLogP3
0.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
114.116 Da
Monoisotopic Mass
114.116 Da
Topological Polar Surface Area
15.300 Ų
Heavy Atom Count
8
Formal Charge
0
Complexity
72.900
Isotope Atom Count
0
Defined Atom Stereocenter Count
1
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
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Recensioni
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Application Protocols
No standardized biological assay protocols apply to this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for practical guidance. When used as a chiral auxiliary/ligand precursor, consult literature procedures specific to the targeted transformation and verify enantiopurity by chiral HPLC/GC.
Biological Roles
Item-specific biological data: Not specified for this item; for research use only.
General context (no clinical claims):
Piperazine rings are prevalent scaffolds in medicinal chemistry, often influencing basicity, solubility, and receptor-binding profiles. N- and C-alkyl substitution modulates pKa and lipophilicity, affecting permeability and target engagement.
Chiral piperazines can impart enantioselective interactions with chiral biomacromolecules, enabling SAR exploration where stereochemistry at the ring carbon is critical.
As a small molecule bearing both tertiary and secondary amine sites, the compound will exist in multiple protonation states at physiological pH, which strongly affects distribution between aqueous and membrane environments (general principle for diamines).
No intrinsic biochemical pathway role is known for (2S)-1,2-dimethylpiperazine itself; rather, it serves as a synthetic intermediate or fragment for constructing bioactive ligands, ionizable linkers, and salt-forming counterions.
Biophysical considerations for conjugates/derivatives (general):
Protonation equilibria: stepwise protonation can shift binding modes and increase water solubility; salt formation with biocompatible acids (e.g., citrate, tartrate) can tune formulation properties of derived molecules.
Metabolic liabilities in derivatives may include N-dealkylation, N-oxidation, and ring-opening under oxidative conditions; stereochemistry at C2 can bias metabolic routes and clearance profiles in derivative series (literature trends).
Buffer Applications
This compound is not a standard buffering agent. While it is a diamine with two basic sites, it lacks the defined pKa spacing and low UV background tailored for biochemical buffer systems.
Not typically used as a buffer: For pH control in the near-neutral range, dedicated piperazine-based buffers (e.g., PIPES, HEPES-like sulfonic acid derivatives) are preferred due to well-characterized pKa, minimal biological interference, and stability.
Practical recommendation:
If a piperazine-derived buffer system is desired, consider PIPES (pKa ~6.8, literature) or EPPS (pKa ~8.0, literature). This product is better suited as a reagent/building block used within an appropriate buffer rather than as the buffer itself.
Green Alternatives
Greenness considerations for this reagent:
As a liquid/low-melting chiral amine, it can replace more volatile, malodorous tertiary amines in some roles, potentially reducing VOC emissions. However, aliphatic amines generally carry aquatic toxicity/odor concerns and require careful waste handling.
Solvent choices to improve EHS profile (general guidance):
Prefer 2-MeTHF, CPME, ethyl acetate, or propylene carbonate over chlorinated solvents where compatible with reactivity and isolation. Alcohols (EtOH/i-PrOH, bio-sourced where possible) are suitable for salt formation and recrystallizations.
Reaction design:
Use catalytic activation (e.g., coupling reagents with improved E-factors or catalytic acylation protocols) rather than stoichiometric halogenating agents. For amide formations, consider greener coupling reagents or enzymatic routes when feasible.
Small comparison (general):
DCM/DMF vs 2-MeTHF/EtOAc: similar solvency for acylations of amines, with significantly better environmental profiles for the latter; be mindful of base solubility and reaction rate trade-offs.
TEA/DIPEA as base vs this reagent: while this product can serve as a base/nucleophile, dedicated hindered bases (e.g., DIPEA) may provide cleaner reactions with fewer quaternization byproducts; choose based on desired chemoselectivity.
Workup and waste:
Capture amine-containing aqueous streams for appropriate treatment; air stripping/activated carbon can mitigate odor. Acidic scrubs can neutralize vapor emissions in scale-up.
Balance green solvent selection with stereochemical integrity and yield; validate alternatives on small scale first.
Pharmaceutical Uses
Item-specific pharmacopeial/excipient status: Not specified for this item; no compendial listing provided.
General formulation/manufacturing context (no therapeutic claims):
Chiral piperazine fragments are widely used as intermediates for drug substance synthesis. (2S)-1,2-dimethylpiperazine can serve as a chiral amine building block for active pharmaceutical ingredient (API) side chains, salt/counterion exploration, or linker installation in conjugates.
Salt formation: readily forms stable mineral-acid salts (e.g., hydrochloride), which can aid isolation, purification, and handling of process intermediates.
Process considerations: control of enantiomeric excess is critical; in multi-kilogram settings, in-line chiral analytics (HPLC) and robust crystallization protocols for salt or derivative forms help maintain stereochemical fidelity.
Extractables/leachables and residuals:
If used as a process reagent, establish purge of residual amine via appropriate workup (acid/base washes) and set acceptance criteria based on safety assessments. Provide GC/LC methods capable of trace-level quantification in final drug substance.
Note: This product is for research use only and is not intended for human or veterinary use.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for small N-alkyl piperazines (informational only):
Physical state: typically low-melting solids or colorless to pale liquids depending on substitution; N- and C-methylation commonly yields a low-viscosity liquid at ambient temperature.
Basicity: two basic sites with distinct pKa values (tertiary amine slightly less basic than secondary amine due to alkyl substitution/inductive effects). Diamines of this class often exhibit stepwise pKa1 ~10–11 and pKa2 ~5–7 (literature, varies with substitution); exact values for (2S)-1,2-dimethylpiperazine are not widely tabulated.
Solubility: miscible with many polar organic solvents (alcohols, ketones, chlorinated solvents) and typically highly soluble in water as the free base; forms stable mineral-acid salts (e.g., hydrochloride) that are freely water-soluble (literature/general).
Volatility and odor: low to moderate volatility; amine odor typical of aliphatic amines (literature/general).
Hygroscopic/CO2 uptake: free bases can absorb CO2 and moisture from air over time, potentially forming ammonium carbamate/carbonate species at the surface (general observation for dialkyl/heterocyclic amines).
Density, refractive index, boiling point, melting point, logP: Not reliably available for this exact stereodefined compound in standard handbooks; consult primary literature or request CoA for measured values.
Note: Use the product’s CoA/SDS for authoritative numeric data when planning quantitative work or safety assessments.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grade for this class of reagent (general guidance):
Research-grade small-molecule amines are commonly offered with assay by GC/GC–MS or NMR, and impurity profiling (residual solvents, related amines). Optical purity (enantiomeric excess) is critical here due to the defined (2S) stereochemistry; look for chiral HPLC/GC data or optical rotation on the CoA.
Water and residual mineral acid content may be reported for amines; Karl Fischer values and amine value/titration can be informative for process use. If unstabilized, check for peroxide/amine oxide or nitrosamine specifications—though such stabilizers are uncommon for this scaffold.
Low-UV vs HPLC grade: For chromatographic applications, “HPLC grade” emphasizes very low non-volatile residue and low UV background. For routine synthesis, “technical” or “research” grade is generally acceptable; polish by distillation over base if needed.
Batch documentation to request when critical:
Assay (area%/wt%), enantiomeric excess, identity by NMR/IR/MS, water (KF), residual solvents, and, when relevant, trace metals (ICP) if used as a ligand precursor.
Note: In absence of a listed grade here, rely on the batch CoA for decision-making.
Reaction and Applications
Building block for chiral piperazine derivatives:
N-acylation, sulfonylation, and carbamate formation at the secondary amine to access chiral auxiliaries, linkers, and protecting-group strategies. The tertiary N can be quaternized or oxidized selectively depending on conditions.
Chiral piperazine derivatives function as bidentate/bifunctional ligands in asymmetric catalysis (e.g., transition-metal-catalyzed additions, hydrogenations) and as bases/nucleophiles in phase-transfer or enamine-type activation when properly derivatized.
Salt and cocrystal formation:
Diamine-derived salts with mineral or organic acids are valuable for resolving chiral acids or as chiral counterions; crystallization from alcohol/ether mixtures is common.
Nucleophilic substitutions and condensations:
Efficient in SN2 alkylations at nitrogen (use non-protic, polar solvents and non-nucleophilic bases to control mono- vs di-alkylation). Forms ureas/thioureas with (thio)isocyanates and amides with acyl chlorides/anhydrides.
Protective group strategies:
Selective protection of the secondary amine (e.g., Boc, Cbz) leaves the tertiary site intact for orthogonal manipulations; subsequent deprotection under acidic or hydrogenolytic conditions.
Practical tips:
Control stoichiometry and order of addition to favor mono-functionalization at the secondary N. Use temperature control for acylations to suppress overreaction. If enantiospecificity matters, avoid conditions that might racemize the C2 stereocenter (strong base, high temperature, or prolonged exposure to enolizable conditions). Analyze ee by chiral HPLC/GC when applicable.
Reaction Conditions
General guidance below is based on related piperazine chemistry and should be optimized experimentally for this specific substrate.
N-Acylation (secondary N):
Typical: acyl chloride (1.0–1.2 eq), base (2.0 eq, e.g., Et3N or NaHCO3), solvent DCM or THF, 0–25 °C, 0.5–4 h. Monitor to avoid overacylation. Expected good to excellent yields for unhindered acyl donors (literature/general).
Carbamate protection (Boc):
Boc2O (1.1–1.5 eq), catalytic DMAP (0.05 eq), base (Et3N, 2.0 eq), MeCN or DCM, 0–25 °C, 1–3 h. Acidic deprotection (TFA/DCM) at 0–25 °C.
Urea formation:
Isocyanate (1.0–1.1 eq), solvent DCM/THF, 0–25 °C; or CDI-activated carboxamides in DMF, 25–60 °C. Secondary amine reacts rapidly; tertiary amine remains unacylated.
N-Alkylation (secondary N):
Alkyl halide/mesylate (1.1–1.5 eq), base K2CO3 or Cs2CO3 (2–3 eq), solvent DMF/MeCN, 20–60 °C, 2–16 h. For minimizing bis-alkylation, use excess amine and slow addition of electrophile.
Quaternization (tertiary N):
Alkyl iodide/bromide (1.1–2.0 eq), neat or MeCN/acetone, 20–60 °C, 1–24 h to furnish quaternary ammonium salts.
Metal-catalyzed coupling on appended handles:
For derivatives bearing aryl/vinyl halides tethered to nitrogen, Pd-catalyzed cross-couplings typically use polar aprotic solvents (DMF/DMAc), 60–120 °C, with standard ligand sets.
Stereochemical integrity:
Avoid strong bases (e.g., LDA, NaH) at elevated temperature that could induce epimerization at C2 via transient carbanion formation; milder conditions and short times are preferred when stereoretention is critical.
Always confirm conditions on small scale and verify chemoselectivity by NMR/LC–MS.
Safety and Handling
Item-specific hazard information: Not specified for this item; refer to SDS for definitive GHS classification, signal word, pictograms, and H-statements.
General safety profile for small aliphatic amines/piperazines (informational only):
Likely hazards: skin/eye irritation or burns, respiratory irritation, and potential sensitization on repeated contact have been reported for related piperazines. Avoid inhalation of vapors/aerosols and skin contact.
PPE: lab coat, nitrile gloves (check compatibility), splash goggles; use in a fume hood to control vapors and minimize odor exposure.
Incompatibilities: strong oxidizers; acid chlorides/anhydrides/isocyanates (violent exotherms/rapid reaction); carbon dioxide (can form salts over time); halogenating agents; nitrosating conditions (to avoid N-nitrosamines). Separate from acids unless intentionally forming salts.
Peroxide formation: not an ether—peroxide formation is not a typical concern; however, amines may auto-oxidize on long exposure to air—store properly.
Spill/first aid (overview; defer to SDS):
Skin/eye contact: immediately flush with water for at least 15 minutes; remove contaminated clothing; seek medical attention as required.
Inhalation: move to fresh air; monitor breathing; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Firefighting: use alcohol-resistant foam, CO2, dry chemical. Amines can form dense smoke and nitrogen oxides upon combustion; SCBA recommended.
Always consult the product-specific SDS for authoritative guidance.
Solvent Selection
This product is a basic, chiral amine reagent rather than a solvent; solvent selection refers to media suitable for its use in synthesis, derivatization, or salt formation.
Polarity and miscibility (general behavior):
Expected to be miscible with polar organics (MeOH, EtOH, i-PrOH, acetone, MeCN, DMF, DMSO) and soluble in moderately polar aprotics (EtOAc, MTBE, DCM). Water solubility is generally high for small piperazines, especially upon protonation.
Solvent choice by task:
N-acylation and carbamate/urea formation: DCM, THF, MeCN, or toluene with a base (or the amine itself as base); control temperature to manage exotherms.
Alkylation/arylation (N- or C-functionalization): polar aprotics (DMF, DMSO, MeCN) often improve rates; consider phase-transfer if using inorganic bases.
Salt formation/resolve: IPA/Et2O/MTBE for crystallization of mineral-acid salts; EtOH/H2O for controlled pH adjustment and salting-out.
Metal-ligand complexation: alcohols, MeCN, or ether solvents as needed for homogeneity.
Comparison with alternatives:
vs. unsubstituted piperazine: higher hydrophobicity and altered basicity can change solubility and selectivity; the chiral center enables enantioselective applications.
vs. tertiary amines (e.g., TEA): offers a secondary amine site for further derivatization; stronger nucleophilicity at the secondary N.
Note: If your application is moisture- or CO2-sensitive, use rigorously dried, degassed solvents and handle under inert atmosphere.
General handling recommendations for aliphatic piperazine derivatives:
Store tightly sealed under air-free or low-moisture conditions to minimize absorption of CO2 and water. If possible, blanket with inert gas (N2/Ar) after opening.
Keep away from strong oxidizers and acids. Use amber or opaque containers if prolonged light exposure is expected, although photo-instability is not typically a concern for saturated amines.
If solidifies at lower temperatures, gently warm to ambient and mix thoroughly before dispensing to ensure homogeneity.
For weighing/dispensing, use clean, dry tools; immediately recap to reduce atmospheric uptake. If a salt form is prepared in-house (e.g., HCl salt), store that material per its specific stability profile (often more air-stable and crystalline).
Reconstitution: Not applicable; supplied neat. If dilution is required, choose dry, oxygen-free solvent when moisture- or CO2-sensitive chemistry is planned.
Always refer to the product CoA/SDS for any lot-specific stability notes and recommended retest intervals.
Structure and Identity
Brief description: (2S)-1,2-dimethylpiperazine is a chiral, N-methylated piperazine bearing a single stereocenter at C-2 of the saturated heterocycle. It is a small, basic, diamine-derived building block and ligand precursor.
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 identity (for reference; not item specifications):
Core scaffold: piperazine (1,4-diazacyclohexane) ring, fully saturated, six-membered with N atoms at 1,4-positions.
Substitution pattern: N1-methyl (tertiary at N1) and a C2-methyl substituent. The C2 carbon is stereogenic; the product name specifies the S configuration at C2.
Functional groups: one tertiary amine (N-methyl), one secondary amine (at the opposite ring nitrogen). Both are basic and nucleophilic; intramolecular hydrogen bonding is limited.
2D structure in words:
A chair-like six-membered ring alternating two nitrogens and four methylene/methine carbons. One ring nitrogen bears a methyl substituent (tertiary amine). The adjacent ring carbon (C2) bears a methyl group set in the S configuration. The distal ring nitrogen remains secondary (N–H). No aromaticity; no additional heteroatoms.
Stereochemistry:
Single defined stereocenter at C2; enantiomeric purity and optical rotation are not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
Functional group handles and reactivity:
Secondary amine (nucleophilic, readily acylated/sulfonylated/alkylated) and tertiary amine (nucleophilic/base; can be quaternized). The ring confers conformational constraint, and the C2 stereocenter provides a handle for asymmetric induction in downstream chemistry.
N-Acylation with acyl chlorides/anhydrides (DCM, Et3N or the amine itself as base) to give amide derivatives; carbamate formation with chloroformates (Boc2O for Boc protection) at the secondary N.
Urea/thiourea synthesis by reaction with (thio)isocyanates; guanidinylation with carbodiimides under appropriate conditions.
Alkylation (SN2) at the secondary nitrogen using alkyl halides/mesylates in polar aprotic solvents; control over-alkylation by stoichiometry, base, and temperature.
Quaternization of the tertiary nitrogen with alkyl halides to access ionic liquids or phase-transfer catalysts; counterion exchange via metathesis.
Metal complexation: derivatized piperazines function as bidentate ligands in Cu, Pd, Ni catalysis; the chiral center can impart asymmetry when embedded into ligand frameworks.
Retrosynthetic value:
Serves as a chiral synthon to introduce a piperazine motif with defined configuration; strategic protection/activation enables selective functionalization, enabling late-stage diversification of libraries or targeted lead optimization.
Target Specificity
Not applicable. This product is a small organic reagent, not a biological targeting reagent (e.g., antibody, probe, or inhibitor with defined target). No antigen/epitope, clone, isotype, or species reactivity applies.
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