2-Chloropropanimidamide , CAS No.5150769

CAS: 5150769 Cat. No.: C1027223 Formula: C₃H₇ClN₂ Peso molecolare: 106.550

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CC(C(=N)N)Cl
• IUPAC Name: 2-chloropropanimidamide
• InChIKey: PINILUABBHQDAD-UHFFFAOYSA-N
• INCHI: 1S/C3H7ClN2/c1-2(4)3(5)6/h2H,1H3,(H3,5,6)
• Peso molecolare: 106.550

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Classe Organonitrogen compounds
      • Subclass Amidines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Classe: Organonitrogen compounds
• Subclass: Amidines
• Intermediate Tree Nodes: Not available
• Direct Parent: Carboxamidines
• Alternative Parents: Carboximidamides Organochlorides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Carboximidamide - Carboxylic acid amidine - Hydrocarbon derivative - Organochloride - Organohalogen compound - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as carboxamidines. These are carboxylic acid derivatives containing the amidine group.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 106.550 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 106.03 Da
• Monoisotopic Mass: 106.03 Da
• Topological Polar Surface Area: 49.900 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 61.800
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 assay or bioanalytical protocols are defined for this item in the Product Data. As a synthetic building block, usage protocols depend on the intended chemical transformation.

• Practical tips (general chemistry):
  • Confirm identity/purity by 1H/13C NMR and HRMS before use; amidines often show characteristic downfield imine proton and broad NH signals.
  • If moisture sensitivity is observed, handle under dry nitrogen/argon and store with desiccant.
  • For substitution chemistry, conduct small-scale condition screens (solvent, base, nucleophile equivalents, temperature) prior to scale-up.

Refer to the Reaction Conditions section for general starting points. For detailed, application-specific procedures, consult the primary literature.

Biological Roles

This product is provided strictly for research use. No biological or clinical efficacy is claimed.

• General context (literature):

  • Amidine functional groups are strongly basic and can be protonated to amidinium ions, which interact with anionic biomolecules (e.g., phosphates and carboxylates) via electrostatics and hydrogen bonding. This property is exploited in research probes and affinity tags.
  • Aliphatic amidines feature in enzyme inhibitors and nucleic acid binders in the literature, but such roles depend on the molecular scaffold and substitution pattern. No biological role is assigned to 2-chloropropanimidamide itself.

• Experimental utility (non-clinical):

  • As a precursor, 2-chloropropanimidamide can be elaborated into cationic ligands or linkers for bioconjugation studies after substitution at C2, allowing tuning of charge and binding properties.

• ADME/tox (general caveats):

  • Amidine cations often exhibit low passive membrane permeability and high aqueous solubility; actual behavior is highly structure- and pH-dependent. No specific ADME data are provided for this item.

For any work involving cells or organisms, ensure appropriate approvals and consult primary literature; this listing does not include suitability for biological systems.

Buffer Applications

2-Chloropropanimidamide is not a standard buffering agent and no buffer system usage is specified for this item.

• Practical note:
  • While amidines are basic and can accept protons, their pKa and chemical reactivity (especially the presence of a reactive C2–Cl) make them unsuitable as primary buffer components.
  • For buffer preparation, use established buffering species (e.g., Tris, HEPES, phosphate) and consult dedicated buffer preparation guides.

For experiments involving this compound, refer instead to the Solvent Selection and Reaction & Applications sections for guidance on media and conditions.

Green Alternatives

Greener practice considerations focus on solvent choice, base/nucleophile selection, and minimizing halide waste when working with 2-chloropropanimidamide.

• Solvent selection (greener options):

  • Replace DMF/DMSO where possible with MeCN, 2-MeTHF, CPME, or renewable alcohols (EtOH) when compatible with the reaction pathway. MeCN offers a good balance of performance and easier recovery.
  • Water or water-organic biphasic systems with phase-transfer catalysts (PTC) can enable SN2 reactions while reducing organic solvent usage.

• Nucleophile/base considerations:

  • Use carbonate or bicarbonate bases instead of strong, hazardous bases when feasible to limit elimination and improve safety.
  • Employ catalytic nucleophile generation (e.g., in situ thiolate from thiol + mild base) to reduce excess reagents.

• Reducing halide footprint:

  • If synthesis route permits, consider tosylate/mesylate intermediates derived from bio-based alcohols as alternative leaving groups, enabling similar reactivity with potentially safer handling compared to chlorides.
  • Apply continuous-flow processing for substitution steps to decrease solvent volume, improve heat/mass transfer, and minimize byproducts.

• Workup and purification:

  • Favor crystallization (e.g., as an amidinium salt) over extensive chromatography.
  • Recycle solvents through in-house distillation; use low-toxicity eluents (EtOAc/EtOH/hexanes alternatives like heptane).

Comparison snapshot (general):

• DMF vs MeCN: MeCN has lower boiling point, easier recovery, and better EHS profile; DMF offers higher SN2 rates but presents reproductive toxicity concerns.
• DCM vs CPME/2-MeTHF: CPME/2-MeTHF reduce chlorinated solvent emissions and often afford comparable outcomes in substitutions or protections.

Pharmaceutical Uses

No pharmacopeial grade or excipient role is specified for this item; it is offered for research use only.

• General context (literature, non-clinical):

  • Amidine-containing motifs frequently appear in medicinal chemistry as cationic headgroups to enhance target binding to acidic residues. 2-Chloropropanimidamide itself is better considered a synthetic intermediate for producing amidine-bearing analogs rather than a formulation component.
  • Salt formation (e.g., hydrochloride) is commonly used to improve handling and crystallinity of amidines during lead optimization and library synthesis.

• Manufacturing/formulation note:

  • If derivatives made from this building block are pursued for preclinical formulation studies, standard characterization (polymorph screening, hygroscopicity, salt/solvate formation) would be undertaken on the final analogs, not on this starting material.

No clinical, therapeutic, or diagnostic claims are made for this product.

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.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed values (reference only; not specifications of this item):

  • Approx. molecular formula (neutral tautomer): C3H7ClN2 (structure-derived).
  • Approx. formula weight: ~106.57 g/mol (calculated).
  • Acid-base behavior: amidines are strongly basic (conjugate acid pKa typically 11–13, literature range for simple aliphatic amidines). Exact pKa for 2-chloropropanimidamide not established here.
  • Expected physical state: low-molecular-weight amidines are often low-melting solids or viscous liquids; hydrochloride salts are often crystalline. Specific MP/BP for this compound not located.
  • Solubility (qualitative, literature-based): free amidines show good solubility in polar protic/aprotic solvents (MeOH, EtOH, MeCN, DMSO, water when protonated). Salt forms (e.g., HCl) are typically water-soluble.
  • Partitioning: amidines are cationic under physiological pH; logP/logD are highly pH-dependent (no specific value located).

• Not provided for this item (do not treat the following as specifications): BP/MP, density, refractive index, UV cutoff, water/peroxide/metal limits. For exact physical data and specifications, consult the item’s CoA/Spec Sheet.

Quality and Grades

• Item-specific (from Product Data):

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

• Guidance on typical grades for small-molecule building blocks (general):

  • Research/Technical grade: suitable for routine synthesis; assay typically >95% by NMR/HPLC/GC with standard impurity profiles. Verify residual solvents and water content on CoA if your synthesis is moisture-sensitive.
  • High-purity/Analytical grade: tightened impurity limits (e.g., low non-volatile residue, controlled UV absorbance) for analytical or medicinal chemistry applications. If UV transparency or trace-metal control are critical, request a detailed specification.
  • Salt form vs free base: amidines are frequently supplied as hydrochloride salts to improve stability and handling. The present listing does not specify the form; confirm on CoA whether material is free amidine or an amidinium salt, as this affects molecular weight, solubility, and stoichiometry.

• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. When present, stabilizers will be listed and may impact downstream reactions.

• Recommendations:

  • Request a current CoA including identification (NMR/IR/HRMS), assay, residual solvents, and moisture.
  • If performing nucleophilic substitution at C2, establish chloride content and assess halide purity by ion chromatography if needed.
  • For quantitative work, standardize against a primary standard or determine active content by qNMR.

Reaction and Applications

2-Chloropropanimidamide is a useful bifunctional synthon that couples a secondary alkyl chloride with a basic amidine, enabling diverse bond constructions.

• Nucleophilic substitution at C2 (general literature patterns):

  • Displacement with amines to access 2-aminopropanimidamides; proceed under polar aprotic solvents (DMF, DMSO, MeCN) with base (e.g., K2CO3, DIPEA). Secondary centers may require elevated temperature or more nucleophilic partners.
  • Reaction with thiols or thiolates yields thioether-substituted amidines; useful for linking to sulfur-containing motifs.
  • Azidation (NaN3) to give 2-azidopropanimidamide as a handle for CuAAC after suitable protection of the amidine if needed.

• Elimination and derivatization:

  • Base-promoted elimination (E1/E2) can furnish propenamidines (vinyl amidines). These serve as precursors to imidines or can participate in hydroamination and further functionalizations.
  • Hydrolysis or transformation of the amidine into amides or nitriles typically requires specific conditions (e.g., oxidative or dehydrating reagents); direct hydrolysis under neutral conditions is slow.

• Protection/activation strategies:

  • Amidine protection (e.g., as Boc-imidamide analogs or via N-alkyl amidinium salts) may be required to direct C2 substitution selectively and suppress N-alkylation.
  • Protonation (HX) affords water-soluble amidinium salts that can simplify handling and crystallization.

• Applications:

  • Linker installation where a cationic amidine is desired for DNA/RNA binding studies (non-clinical), surface charge modulation, or affinity tagging.
  • Precursor to chiral derivatives at C2; resolution or asymmetric substitution may generate enantioenriched products.

Note: Optimize conditions for secondary-alkyl chloride substitution; competing elimination and N-alkylation are common bypaths.

Reaction Conditions

The following are general, literature-style guidelines for related secondary-alkyl chloride amidines; they are not product specifications. Optimize per substrate and scale.

• SN2 displacement at C2 (amines):

  • Solvent: MeCN or DMF (anhydrous).
  • Base: K2CO3 (2–3 equiv) or DIPEA (2–4 equiv).
  • Nucleophile: primary amine (1.2–2.0 equiv).
  • Temperature: 50–90 °C (lower with more reactive nucleophiles).
  • Time: 4–24 h.
  • Notes: Minimize protic solvents to suppress solvolysis; consider amidine protection to avoid N-alkylation.

• Thioether formation (thiolate substitution):

  • Solvent: DMF/DMSO or 2-MeTHF with PTC.
  • Base: K2CO3 or NaH (care with exotherm) to generate thiolate in situ.
  • Temperature: 25–60 °C.
  • Time: 2–8 h.
  • Notes: Oxygen exclusion reduces disulfide formation.

• Azidation (to 2-azido derivative):

  • Solvent: DMSO or DMF.
  • Reagent: NaN3 (1.5–3 equiv).
  • Temperature: 50–80 °C.
  • Time: 4–16 h.
  • Notes: Handle azides with appropriate safety; protect amidine if CuAAC planned downstream.

• Elimination to vinyl amidine:

  • Base: t-BuOK or DBU (1.2–2.0 equiv).
  • Solvent: THF, t-BuOH, or MeCN.
  • Temperature: 25–60 °C.
  • Time: 1–6 h.
  • Notes: Competes with substitution; monitor by LC–MS/GC if feasible.

Yields vary widely (30–90%) depending on nucleophile strength, sterics, and protection strategy; small-scale scouting is recommended.

Safety and Handling

• Item-specific hazard data (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.
  • Research Use: For research use only.

• General safety considerations for chloro-substituted amidines (literature/general guidance):

  • Irritation/corrosivity: amidines are basic and may cause skin and eye irritation; salt forms can also be irritating. Handle with appropriate PPE (lab coat, gloves, splash goggles).
  • Reactivity: secondary alkyl chlorides can undergo nucleophilic substitution or elimination; avoid strong nucleophiles or bases unless intended. Avoid contact with strong oxidizers and strong acids/bases unless controlled.
  • Volatility/odor: low volatility expected; nevertheless, handle in a fume hood to avoid inhalation of aerosols or vapors.
  • Sensitization: no specific data; avoid repeated skin contact.
  • Spill/first aid (overview):
    • Skin/eye contact: rinse with copious water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
    • Inhalation: move to fresh air; seek medical advice if symptoms occur.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Storage incompatibilities and precautions (general):

  • Store tightly closed at room temperature as per Product Data, in a dry, well-ventilated area.
  • Protect from moisture and CO2 which can alter basic nitrogen speciation; desiccant recommended after opening.
  • Use only non-sparking tools if handling large quantities of organic powders; ground containers during transfer to minimize static.

Always consult the product’s SDS for authoritative hazard classification and response measures.

Solvent Selection

Because 2-chloropropanimidamide is both basic (amidine) and electrophilic at C2 (secondary chloride), solvent choice should balance solubility with control of substitution/elimination pathways.

• Polarity and miscibility (general expectations):

  • High solubility in polar aprotic media (DMSO, DMF, NMP, MeCN) for SN1/SN2 or S-alkylation/N-alkylation chemistry.
  • Good solubility in polar protic alcohols (MeOH, EtOH), especially under acidic conditions (amidinium formation), though protic media can compete in solvolysis.
  • Limited solubility anticipated in nonpolar hydrocarbons unless converted to a less polar derivative.

• When to choose specific solvents (general guidance):

  • Nucleophilic substitution at C2 (amines, azides, thiols): use polar aprotic solvents (DMF, DMSO, MeCN) to enhance nucleophile reactivity; control temperature to limit elimination.
  • Elimination to give vinyl amidine: employ strong base in polar aprotic solvents; monitor for over-reaction/polymerization.
  • Salt handling/purification: aqueous alcohol or water with pH control can help dissolve amidinium salts; consider ion-exchange or pH-switch extraction.

• Compatibility notes:

  • Amidine nitrogen can coordinate metals; if using transition-metal catalysis, consider solvent/ligand systems that maintain catalyst activity (MeCN or alcohols often suitable).
  • Avoid strongly acidic chlorinated solvents during prolonged heating to minimize undesired solvolysis or rearrangement.

• Small comparison (general):

  • DMF/DMSO: maximize SN2 rates; harder to remove; consider high-vacuum and co-evaporation.
  • MeCN: good balance of polarity and volatility; may require longer times than DMF/DMSO.
  • Alcohols: enable ionization; risk of solvolysis/ether formation under strong acid.

Storage and Reconstitution

• Item-specific (from Product Data):

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

• General storage guidance for small amidines:

  • Store in a tightly sealed container under dry, inert atmosphere if possible, especially after opening, to limit moisture uptake and CO2 interaction.
  • Protect from prolonged exposure to light and heat; room temperature is acceptable per Product Data, but avoid temperature cycling.
  • If supplied as a salt (e.g., HCl), keep desiccated to prevent caking; note that salts are typically more air-stable.

• Reconstitution and handling (general):

  • Solubility: dissolve in polar aprotic solvents (MeCN, DMF, DMSO) or alcohols (MeOH, EtOH). For aqueous work, adjust pH acidic to form the amidinium for improved solubility.
  • Filtration: if particulates are present, pre-filter through 0.2 µm PTFE (organic) or PES (aqueous) membranes.
  • Stock solutions: prepare single-use aliquots to minimize freeze–thaw; label with solvent, concentration, and date. For DMSO/MeCN stocks, store refrigerated if long-term stability is uncertain; verify stability by LC–MS before critical experiments.

For definitive storage, stability, and reconstitution instructions, always refer to the product’s CoA and SDS.

Structure and Identity

Brief description: 2-Chloropropanimidamide is a small, bifunctional organic building block combining a secondary alkyl chloride with a terminal amidine (–C(=NH)–NH2), enabling both electrophilic substitution at C2 and amidine-based transformations.

• Item-specific (from Product Data):

  • SKU: C1027223
  • Product Name: 2-Chloropropanimidamide
  • CAS: 5150769
  • Storage Conditions: Room temperature
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: 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.

• Literature/computed (for reference only; not product specifications):

  • Likely constitutional formula for the neutral amidine tautomer: CH3–CH(Cl)–C(=NH)–NH2 (substitution at C2 of the propan backbone adjacent to the amidine carbon).
  • Approximate molecular formula (neutral tautomer): C3H7ClN2 (literature/structure-derived).
  • Approximate formula weight: ~106.57 g/mol (calculated from C3H7ClN2).
  • Possible SMILES (neutral amidine tautomer): NC(=N)C(Cl)C

• Structural features (general description):

  • Functional groups: secondary alkyl chloride (at C2), mono-substituted amidine (–C(=NH)–NH2).
  • Electron distribution: the amidine carbon is sp2; the adjacent C2 bearing Cl is benzylic-like in activation (alpha to a C=N), increasing the propensity for substitution or elimination under appropriate conditions.
  • Tautomerism: amidines exist as imino-amino tautomers; protonation yields amidinium salts under acidic conditions.
  • Stereochemistry: the molecule can be chiral at C2; commercial material may be racemic unless specified (no stereochemical specification provided for this item).

Synthetic Utility

Key reactivity arises from the juxtaposition of a secondary alkyl chloride at C2 and a basic amidine terminus.

• Functional group handles:

  • Secondary alkyl chloride (C2–Cl): electrophilic center enabling SN1/SN2 substitutions with N-, O-, S-, and C-nucleophiles; prone to elimination under strong base/heat.
  • Amidine (–C(=NH)–NH2): strong base/nucleophile that can be protonated (amidinium) or protected; participates in acylation, alkylation (N-alkylation), and can coordinate metals.

• Strategic roles:

  • Divergent synthesis: install diverse substituents at C2 via substitution, then fine-tune basicity/solubility through N-derivatization of the amidine.
  • Access to vinyl amidines: one-step elimination provides alkenyl amidines, which are versatile in hydrofunctionalizations and can be cyclized to heterocycles (e.g., imidazolines under suitable conditions, literature-dependent and often requiring additional functionalities).
  • Linker chemistry: serve as a cationic linker precursor in conjugation workflows after displacement of chloride by a nucleophile bearing the desired functional group.

• Selectivity considerations:

  • N- vs C-alkylation: nucleophiles may compete with internal N-alkylation of the amidine; temporary protection of the amidine (e.g., as an amidinium salt or N-protected variant) can improve C2 substitution yields.
  • Stereochemistry at C2: substitution at a chiral center can proceed with inversion (SN2) or racemization (via carbocation in SN1-like pathways). Choose conditions accordingly.

• Workup/purification:

  • Convert crude products to crystalline salts (e.g., HCl, p-TsOH) for purification; reverse to free base as needed.
  • Monitor reactions by LC–MS using a volatile mobile phase (ammonium formate/acetate) to accommodate basic analytes.

Target Specificity

Not applicable. This product is a small-molecule building block and not a biologic/antibody/assay reagent. No target, epitope, or isotype information is provided or applicable for this item.