2-Methylpropanimidamide - ≥95% , CAS No.57536-10-4

CAS: 57536-10-4 Cat. No.: M1073956 Formula: C₄H₁₀N₂ Molecular Weight: 86.14

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

• Molecular Weight: 86.14

Chemical and Physical Properties

• Molecular Weight: 86.140 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 86.0844 Da
• Monoisotopic Mass: 86.0844 Da
• Topological Polar Surface Area: 49.900 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 56.600
• 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

No antibody/assay kit application data are associated with this small molecule. Protocols depend on the intended synthetic or formulation use.

• General handling (research use)
  • To prepare an aqueous stock (salt form): Dissolve amidinium salt in water or buffer to desired concentration; filter (0.22 µm) if sterility is required. Record pH, as protonation state can affect assay outcomes.
  • To generate the free base from a hydrochloride: Suspend salt in water, basify to pH > 10 with NaOH, extract with anhydrous ethyl acetate or DCM, dry (Na2SO4), and evaporate under reduced pressure. Use immediately or store under inert atmosphere.
  • For N‑alkylation screens: Prepare 0.1–0.5 M solutions in dry DMF/MeCN; add electrophile (1.1 eq) and base (1.5 eq); stir at rt to 60 °C; monitor by LC‑MS.

Item‑specific, tested application conditions and recommended dilutions: Not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

This product is supplied strictly for research use; no clinical/therapeutic claims are made.

• General biochemical context for amidines (literature; not item‑specific)

  • Charge state: Amidines are strongly basic and largely protonated (amidinium) at physiological pH, conferring persistent positive charge and strong hydrogen‑bond donor capability.
  • Molecular recognition: Amidinium groups form tight ion pairs with carboxylates (Asp/Glu) and interact with phosphates and sulfates. They are common motifs in protease inhibitors and affinity ligands, owing to electrostatic and H‑bonding complementarity.
  • Biotransformation: Primary aliphatic amidines can undergo N‑oxidation, N‑dealkylation, and hydrolysis to amides or amines under enzymatic conditions (literature). Salt forms influence absorption and distribution in biological matrices.
  • Conjugation chemistry: The two nitrogens allow selective functionalization (e.g., formation of amidoximes or N‑acyl derivatives) used to tune binding or solubility in probe molecules.

• Practical implications for lab studies

  • Expect strong interactions with negatively charged biomacromolecules; binding can be highly pH‑dependent.
  • Use buffered systems to control protonation; amidinium salts increase aqueous solubility for assay stock solutions.

For any work involving biological systems, confirm purity, counterion, and endotoxin/bioburden requirements as applicable (not specified for this item; refer to CoA/Spec Sheet).

Buffer Applications

2‑Methylpropanimidamide is not a standard buffering agent. While amidines are strongly basic and can accept protons, their pKa values and limited conjugate acid ranges do not align with common biological buffer windows.

• Guidance
  • Not typically used to prepare defined buffer systems. If a positively charged additive is desired, prepare an amidinium salt (e.g., HCl) and add to an established buffer (e.g., phosphate, HEPES) to adjust ionic strength or probe electrostatic interactions.
  • For pH control in the 7–9 range, choose dedicated buffers (e.g., HEPES, Tris, TAPS) with well‑characterized buffering capacities.

For any buffer‑like application, verify compatibility with your assay components and confirm the salt form and concentration. Item‑specific buffer data are not provided here; refer to CoA/Spec Sheet if needed.

Green Alternatives

Context: As a nitrogenous building block, 2‑methylpropanimidamide is not readily substituted one‑for‑one by a “green solvent.” Greenness considerations focus on solvent/media choices and safer reagents in transformations involving this amidine.

• Greener media (literature guidance)

  • Prefer water/ethanol or water/i‑PrOH for salt formation, recrystallization, and ion exchange when feasible.
  • Replace DMF/DMSO with safer dipolar aprotics (e.g., propylene carbonate, Cyrene, N‑butylpyrrolidone) where reaction scope allows.
  • Use acetonitrile judiciously; consider 2‑MeTHF or ethyl acetate for extractions and crystallizations.

• Benign reagents/conditions

  • Employ carbonate bases (K2CO3, Cs2CO3) instead of strong alkoxides where compatible to reduce hazards.
  • Utilize organocatalytic or enzyme‑mediated N‑acylations in aqueous media when selectivity permits.

• Tradeoffs

  • Polar green solvents (e.g., propylene carbonate) may complicate workup due to high boiling points.
  • Water/alcohol systems can increase salt formation and reduce nucleophilicity of the amidine, requiring higher temperatures or phase‑transfer catalysis.

• Small comparison (general)

  • Conventional: DMF, DMSO, MeCN for N‑alkylation/acylation; dichloromethane for extractions.
  • Greener leaning: Propylene carbonate/Cyrene/NBP for coupling; 2‑MeTHF/EtOAc for workup; water/ethanol for salt operations.

Implement process mass intensity (PMI) tracking and solvent recycling to realize the main environmental gains when using amidines.

Pharmaceutical Uses

No therapeutic claims are made. The following refers to formulation/manufacturing roles in a general research context.

• General roles for amidines in pharma R&D (literature)

  • Synthetic intermediate: Primary amidines serve as building blocks for more complex amidines, amidoximes, guanidines, and heterocycles; useful in medicinal chemistry SAR campaigns to install a cationic headgroup.
  • Salt formation: Amidinium salts can enhance aqueous solubility for discovery formulations and screening stocks.
  • Ion‑pairing excipient (research scale): Cationic amidinium species can form ion pairs with acidic drugs to modulate crystallization or extraction during process development (case‑by‑case; not routine excipient use).

• Compliance/monographs

  • No pharmacopeial monograph is indicated for 2‑methylpropanimidamide (not specified for this item; refer to CoA/Spec Sheet). For any application in regulated settings, full GMP qualification, impurity profiling, and residual solvent analyses are required.

• Practical notes

  • Verify counterion content and water content for accurate dosing in preformulation.
  • Evaluate hygroscopicity and solid‑state form (free base vs salt; polymorph) to ensure reproducible handling.

Item‑specific excipient status, residuals, and bioburden/endotoxin: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

• Product Data (item-specific)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting/Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
  • Refractive index/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general expectations (for primary aliphatic amidines; not item specifications)

  • Acid–base: Amidines are strongly basic; conjugate acid pKaH typically ~12–13 (literature, varies with substitution). Consequently, the free base is readily protonated under neutral/acidic conditions, forming water‑soluble amidinium salts (e.g., hydrochloride).
  • Polarity/solubility: Free bases can be hygroscopic and moderately polar; salts exhibit high water/methanol solubility. The branched C4 group adds some hydrophobicity relative to acetamidine/ethanimidamide.
  • Volatility: Low for salts; free base may be low‑to‑moderate volatility compared to amines of similar MW due to hydrogen bonding and potential dimerization via N–H···N interactions.
  • Physical state: Small aliphatic amidines are often low‑melting solids or viscous liquids (free base) and crystalline solids as mineral acid salts.

Note: For authoritative values (mp/bp, density, water or metal content, stabilizers), consult the CoA/Spec Sheet for this specific lot/item.

Quality & Grades

• Product Data (item-specific)

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

• Interpreting grades (general guidance)

  • Research grade: Suitable for most synthetic and biochemical research. Typical controls include identity (NMR/IR/MS), purity by HPLC/GC, and residual solvent testing. If your application is moisture‑sensitive or requires low UV background, confirm specifications for water content and UV absorbance.
  • Salt form vs free base: Amidines are frequently offered as hydrochloride salts to enhance stability and handling. Verify the form (free base or specific salt) on the CoA; stoichiometry affects assay (%), molecular weight, and solubility.
  • Trace impurities: For catalysis or analytical applications, check for metal content, residual mineral acid, and neutral amine/amidoxime byproducts. If not listed here, these parameters are Not specified for this item; refer to CoA/Spec Sheet.

• Practical recommendations

  • Confirm identity and counterion (if salted) before stoichiometric use.
  • If low UV background is needed (e.g., UV detection), request a chromatographic grade or examine the UV spectrum of the lot.
  • For moisture‑sensitive reactions with the free base, consider in situ generation from the salt with base under anhydrous conditions.

Reaction & Applications

• Functional profile

  • 2-Methylpropanimidamide is a primary amidine (R–C(=NH)–NH2). The amidine motif is both nucleophilic and strongly basic, enabling derivatization at either nitrogen and participation in salt formation with acids.

• Representative reaction families (literature/general)

  • N‑Alkylation: Formation of mono‑ and di‑N‑alkyl amidines using alkyl halides/tosylates in polar aprotic solvents (DMF/MeCN) with controlled base. Competing overalkylation can be mitigated with stoichiometry and temperature control.
  • Acylation/Carbamoylation: Reaction with acyl chlorides, carbonates, or CDI to give amidinium carboxylates or urea‑like derivatives. Useful in protecting group strategies and ligand synthesis.
  • Salt formation and ion pairing: Readily forms amidinium salts (e.g., HCl, HBr, p‑TSA) for improved stability, crystallinity, and aqueous solubility; reversible under basic conditions.
  • Condensation/Imidate exchange: Amidines can engage in equilibria with imidates/oxazolines under acidic conditions (Pinner‑type chemistry, literature), enabling interconversion among C–N functional groups.
  • Ligand/templating roles: Amidines chelate metals upon deprotonation (amidinate ligands), though primary amidines more commonly serve as precursors to N,N′‑disubstituted amidinates.

• Practical tips

  • Drying: The free base is hygroscopic and absorbs CO2; handle under inert gas for moisture/CO2‑sensitive work.
  • Selectivity: Protonation state dictates site selectivity; the imine‑like nitrogen is typically less nucleophilic than the amine‑like nitrogen.
  • Analysis: Track reactions by LC‑MS (M+H+ expected) and 1H NMR (diagnostic =NH signal often broad; exchangeable with D2O).

Reaction Conditions

The following are literature‑style generalizations for amidine manipulations; they are not specifications for this item.

• N‑Alkylation (to secondary amidines)

  • Typical: R–X (1.0–1.2 eq), K2CO3 or Cs2CO3 (1.5–2.0 eq), DMF or MeCN, 0–25 °C to 60 °C, 2–16 h. Monitor for over‑alkylation at the second nitrogen.
  • Alternative: Phase‑transfer (TBAB) in toluene/MeCN with aqueous base for greener profile; extended times may be needed.

• N‑Acylation/Carbamoylation

  • Reagents: Acyl chloride/anhydride (1.1–1.5 eq) or CDI‑activated acids; solvent DCM, THF, or MeCN; base triethylamine or DIPEA (1–2 eq); 0 °C to rt, 1–6 h. Quench into aqueous bicarbonate.

• Salt formation/exchange

  • Dissolve free base in EtOH or i‑PrOH; add HCl or other acid in alcohol/ether (1.0–1.1 eq) at 0–10 °C; stir to crystallization; isolate by filtration and dry under vacuum.

• Metalation (for amidinate precursors)

  • Strong base (n‑BuLi or NaH) at −78 to 0 °C in THF/Et2O to form N‑deprotonated species, then trap with metal halide; applicable mainly to N,N′‑disubstituted amidines.

• Workup/purification

  • Amidinium salts crystallize readily; free bases may require column chromatography on neutral alumina or reversed phase if polar.

Expected yields for such transformations vary broadly (50–90% commonly reported) depending on substrate and conditions; confirm with small‑scale trials.

Safety & Handling

• Product Data (item-specific)

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H‑Statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety considerations for aliphatic amidines (literature guidance; not item-specific)

  • Hazards: Primary amidines are strong bases and can be irritating to skin, eyes, and respiratory tract. Protonated salts may be corrosive depending on counterion and concentration. Avoid inhalation of dust/vapors and contact with skin/eyes.
  • PPE: Use lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Handle within a fume hood to minimize exposure.
  • Incompatibilities: Strong oxidizers; strong electrophiles/acylating agents; CO2 (for free bases, can form carbamate-like adducts); avoid contact with acids/bases that could lead to exothermic neutralization if large quantities are mixed.
  • First aid (overview): Eye/skin contact—rinse with water for ≥15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; do not induce vomiting; seek medical attention. Provide SDS to responders.
  • Spill/cleanup: Contain and absorb with inert material. Avoid generating dust/aerosols; ventilate area. Dispose per local regulations.

Always defer to the product‑specific SDS for authoritative hazard classification and response procedures.

Solvent Selection

This product is a small, strongly basic, hydrogen‑bonding organic compound rather than a solvent; selection focuses on media for handling and reactions.

• General solvent compatibility (literature guidance)

  • Protic polar: Water, methanol, ethanol—excellent for amidinium salts; promote protonation and high solubility.
  • Aprotic polar: DMSO, DMF, acetonitrile—good for both free base and salts; useful for coupling or N‑functionalization.
  • Nonpolar: Limited solubility for salts; the free base may dissolve in dichloromethane, ethyl acetate, or MTBE to a modest extent, aided by H‑bonding or formation of ion pairs if partially protonated.

• Choosing conditions

  • For nucleophilic N‑functionalization (e.g., alkylation): Use dry, aprotic solvents (DMF, DMSO, MeCN); control basicity with mild inorganic bases to favor mono‑ vs di‑alkylation.
  • For salt exchange: Dissolve in water/alcohol, treat with corresponding acid/base, and remove solvent under reduced pressure.
  • For crystallization: Amidinium salts often crystallize well from alcohol/ether or alcohol/acetone mixtures.

• Quick comparison (general)

  • Water/MeOH: Maximizes solubility of salts; convenient for ion exchange and bioconjugation contexts.
  • Acetonitrile/DMF: Favor SN2 alkylations and acylations with minimal proton transfer side reactions.
  • DCM/EtOAc: Useful for workups/extractions; free base partitions into organic phase at high pH.

Storage & Reconstitution

• Product Data (item-specific)

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

• General storage guidance for amidines (literature; adapt to form)

  • Free base: Store tightly sealed at ambient temperature in a desiccator; protect from atmospheric CO2 and moisture. An inert gas blanket (N2/Ar) is beneficial for long‑term stability.
  • Salt forms (e.g., HCl): Typically more stable at room temperature; store in a dry place away from strong bases and oxidizers.
  • Light sensitivity: No specific photolability is expected for saturated amidines, but opaque or amber containers minimize unforeseen degradation.

• Reconstitution

  • For assay stocks: Prepare in water, methanol, ethanol, or DMSO depending on salt/free base. Filter sterilize if needed. Document concentration and pH.
  • For synthetic use: If supplied as a salt, generate the free base in situ with a stoichiometric base (e.g., DIPEA) in anhydrous solvent immediately before reaction to limit moisture uptake.

• Freeze–thaw

  • Not generally required; if solution stocks are prepared, store aliquots at −20 °C to avoid repeated freeze–thaw. Inspect for precipitation or pH drift upon thawing.

For any parameters not listed above (e.g., exact solvent compatibility, hygroscopicity, assay), Not specified for this item; refer to CoA/Spec Sheet.

Structure & Identity

Brief overview: 2-Methylpropanimidamide is an aliphatic primary amidine (imidamide) derived from 2-methylpropanoic (isobutyric) backbone; it contains the cationic amidine motif C(=NH)–NH2.

• Product Data (item-specific)

  • SKU: M1073956
  • CAS: 57536-10-4
  • Storage Conditions: Room temperature
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (general reference, not item-specific specs)

  • Common/Preferred name: 2-Methylpropanimidamide (aka isobutanimidamide)
  • Functional groups: Primary amidine (C(=NH)–NH2); branched isopropyl substituent at the α-carbon
  • Typical neutral free-base depiction: CC(C)C(=NH)NH2 (SMILES, literature); many databases also list CC(C)C(=N)N
  • Typical molecular formula (free base, literature): C4H10N2
  • Typical molecular weight (free base, literature): ~86.14 g/mol

• 2D structural description (general)

  • A four‑carbon skeleton with a 2-methyl (isopropyl) substitution adjacent to the amidine carbon. The terminal carbonyl of an amide is replaced by the amidine C(=NH)–NH2 functionality, featuring one imine-like nitrogen (=NH) and one primary amino nitrogen (–NH2). The amidine carbon is sp2 hybridized; no stereocenters are present. The isobutyl fragment (–CH(CH3)2) provides hydrophobic character juxtaposed with a strongly basic, cationic-capable headgroup.

Synthetic Utility

• Functional group leverage

  • The amidine C(=NH)–NH2 unit is bifunctional: a strong base and a nucleophile at nitrogen. It enables rapid formation of salts and derivatives, making 2‑methylpropanimidamide a versatile synthon for cationic motifs.

• Transformations (literature/general)

  • N‑Alkylation to secondary/tertiary amidines using alkyl halides/mesylates; control mono‑ vs di‑alkylation by stoichiometry and base.
  • N‑Acylation and carbamoylation with acyl chlorides, anhydrides, CDI, or activated esters to give amidinium carboxylates/urea‑like products.
  • Conversion to amidoximes via reaction of corresponding nitrile precursors (Pinner sequence); amidines also partake in cyclizations to imidazolines/imidazoles under dehydrating conditions.
  • Metal complexation after N‑deprotonation to generate amidinate ligands (typically from N,N′‑disubstituted amidines; primary amidines can be precursors).
  • Salt switches (HCl, HBr, sulfate, p‑TSA) to tailor crystallinity, solubility, and processability.

• Retrosynthetic value

  • As the cationic headgroup donor in lead optimization, swapping an amine for an amidine can raise pKaH and strengthen binding to acidic targets while modulating permeability via branching (isobutyl).

• Practicalities

  • Use dry conditions for free‑base chemistry; quench with care due to strong basicity.
  • Characterize derivatives by NMR (exchangeable N–H), IR (νC=N ~1650–1680 cm⁻¹, νN–H broad), and HRMS (M±H).

Target Specificity

This product is a small‑molecule building block, not a biological targeting reagent. No antigen/epitope/clone/isotype information applies.

• Item-specific target data: Not applicable.
• If used in biological assays, interactions will be non‑specific electrostatic/hydrogen‑bonding typical of amidinium groups rather than selective binding to a defined target.