GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.
This compound belongs to the class of organic compounds known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
External Descriptors
a small molecule
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.
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Application Protocols
Not applicable to this material type. No tested biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic uses, see Reaction & Applications and Reaction Conditions sections for general guidance.
Biological Roles
General, literature-based context (no clinical claims)
Functional motif
The guanidinium group is central to biological recognition due to strong bidentate H‑bonding and cation–π interactions. It underlies the side chain of L‑arginine, is present in creatine/creatinine, and is widely exploited in protein–ligand recognition.
Protonation state and transport
At physiological pH, guanidine exists predominantly as guanidinium (positively charged), influencing membrane transport and binding to acidic biomolecules.
Metabolic occurrence
Trace levels of guanidine and small guanidino compounds appear in mammalian metabolism as byproducts of amino acid and nitrogen handling pathways; they are typically efficiently cleared.
Chaotropic effects
Notably, guanidinium salts (e.g., guanidinium chloride/thiocyanate) are classical protein denaturants used in biochemistry. The free base is rarely used directly in biochemical assays but is a conceptual precursor to these reagents.
Binding paradigms
Guanidinium engages carboxylates, phosphates, and aromatic residues via strong Coulombic and H‑bond networks, a principle leveraged in designing arginine-mimetic ligands.
Note: This section reflects general biochemical knowledge of the guanidinium functionality; item-specific biological testing is not part of this product listing (Research Use Only).
Buffer Applications
Guanidine (free base) is not typically employed as a buffering agent.
Rationale
With a conjugate acid pKa ~13.6 (literature), the guanidine/guanidinium pair buffers far outside conventional laboratory pH ranges. In water, guanidine acts primarily as a strong base rather than a buffer.
Practical guidance
For basic buffers in the pH 9–11 range, consider alternatives such as CAPS (pKa 10.4), CHES (pKa 9.3), or carbonate/bicarbonate systems.
Denaturing/chaotropic applications
Protein denaturation and nucleic acid extraction workflows commonly use guanidinium salts (e.g., guanidinium chloride, guanidinium thiocyanate), not the free base. Select the appropriate salt if a chaotrope is required.
Green Alternatives
Context: Guanidine is a strong, non-metal organic base and a synthon for guanidinium groups. Greener selection hinges on solvent, energy input, and replacement by less hazardous bases when feasible.
Greener base options (literature/general)
Carbonate/bicarbonate bases (K2CO3, NaHCO3): Benign, low hazard; adequate for many SNAr, alkylations, and condensations in polar aprotics but weaker than guanidine.
Organic superbases (DBU) often allow catalytic loadings; although stronger, they can be used at lower quantities, reducing waste; however, they may have higher toxicity and persistence.
Biobased amines (e.g., ethyl carbonate-derived alkoxides formed in situ from EtOH/Na2CO3) can be generated with lower EHS burden for transesterifications.
Solvent considerations
Prefer water, ethanol, or 2-MeTHF over chlorinated or high-VOC aromatics when compatible with the transformation.
Trade-offs
Replacing guanidine may reduce basicity or nucleophilicity; yields/chemoselectivity can shift.
Guanidine’s metal-free nature avoids metal contamination—valuable for catalytic material screens—so alternatives introducing metals (alkoxides) may be less green in specific contexts.
Comparison snapshot (general)
Guanidine vs K2CO3: Higher basicity; better for challenging deprotonations; K2CO3 offers better EHS profile.
Guanidine vs DBU/TBD: Lower potency and often higher loadings for guanidine, but simpler handling waste stream; DBU/TBD can cut reaction time/temperature at the cost of more specialized EHS controls.
Pharmaceutical Uses
No therapeutic claims. Context below pertains to formulation/manufacturing and synthetic intermediates.
Role in API synthesis (general)
Guanidine is a key building block for installing guanidinium motifs present in numerous drug candidates (arginine mimetics, kinase inhibitor warheads, transporter-targeting cations).
Used to access substituted guanidines, biguanides, and heterocycles via guanidinylation and cyclocondensation routes.
Excipients/formulation
The free base is not a common excipient due to its strong basicity and reactivity. Guanidinium salts (e.g., guanidinium chloride) may appear as processing aids in specific bioprocessing steps, but these are distinct materials.
Regulatory status
Pharmacopeial monographs typically address salts (e.g., guanidine hydrochloride) rather than the free base. For cGMP or regulated use, verify suitability and specifications with QA and consult the relevant pharmacopeia.
Manufacturing considerations
Metal-free basic conditions can be advantageous when downstream catalytic steps are metal-sensitive.
Manage CO2/moisture exposure to maintain assay and reproducibility across batches.
Physical Properties
Only literature/general values are provided below for context. They are not item-specific specifications.
Phase/appearance (literature): Colorless to white crystalline solid; hygroscopic; strong amine-like odor.
Melting point (literature): ~50–52 °C (may decompose/effervesce due to CO2 uptake if exposed to air).
Boiling point (literature): Reported decomposition before/around ~160–170 °C at ambient pressure; distillation not recommended.
Density (literature): Approximately 1.3 g/cm³ at 20–25 °C (reports vary; hygroscopicity affects apparent density).
Refractive index: Not applicable (solid); aqueous solutions show nD similar to water, concentration dependent.
Notes for practitioners
The free base avidly absorbs CO2 and moisture, forming guanidinium carbonate/bicarbonate mixtures; measured properties can drift with air exposure.
For precise property needs (e.g., DSC/TGA values, UV cutoffs, trace metals), Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item grade (Product Data): Moligand™
Interpretation and context
Moligand™ (general description): Aladdin’s screening/ligand-focused quality designation intended for small-molecule libraries and discovery chemistry. Materials under this designation are suited for structure–activity exploration, parallel synthesis, and fragment/ligand development workflows.
What this implies for use (general guidance)
Emphasis on identity and suitability for research synthesis; not intended for clinical, diagnostic, or food use.
UV/LC background, trace impurities, water/peroxide content, and metal levels: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives
None stated for this product. If stabilizers are present in a specific lot, they will be listed on the CoA.
Documentation and verification
For sensitive applications (e.g., catalytic screening, surface-sensitive analytics), verify lot-specific attributes (assay, residual solvents, water content) on the CoA before use.
Note: Always match handling to your application’s requirements; if low-UV, LC/MS, or trace-metal specifications are critical, contact Technical Support for an appropriate grade.
Reaction and Applications
Use cases emphasize guanidine’s strong basicity and its role as a nucleophilic synthon for guanidinium frameworks.
As a base (general/literature)
Promotes condensations and rearrangements that tolerate protic conditions (e.g., Knoevenagel-type condensations in aqueous alcohols), ester aminolysis, and selective deprotonations of moderately acidic substrates (pKa ≤ ~13 in water) where inorganic bases underperform.
Serves as a mild, non-metal base for reactions where metal contamination is a concern.
As a nucleophile/guanidinylation synthon
Formation of N,N′-disubstituted guanidines by reaction with electrophiles such as chloroformamidines, imidates, or carbodiimides (e.g., CDI-activated amines/imidates), providing access to biguanides, arginine mimetics, and heterocycles.
Reaction with isothiocyanates to give thiourea-type intermediates that can be transformed to guanidine derivatives (via desulfurization/transfer chemistry).
Heterocycle construction
Precursor to aminoguanidines and subsequent 1,3,4,5-tetraaza frameworks; used in synthesis of dihydropyrimidines and 1,2,4-triazines via cyclocondensations with appropriate di-electrophiles (e.g., 1,3-dicarbonyl derivatives or cyanoguanidine routes).
In polar aprotic media, add a small proportion of alcohol to aid dissolution, or employ phase-transfer catalysts if using heterogeneous conditions.
When targeting selective mono- vs di-guanidinylation, control stoichiometry and order of addition; protect/labilize amine partners as needed.
Reaction Conditions
General literature guidance; optimize per substrate.
As a base
Solvents: Water, MeOH, EtOH, or mixed aqueous-organic systems; in aprotic media add a protic co-solvent for solubility.
Temperature: Ambient to 60 °C typically; monitor exotherm on dissolution and neutralizations.
Loadings: Stoichiometric for neutralizations/deprotonations; 0.1–1.0 equiv for base-promoted condensations depending on acidity of the pronucleophile.
Guanidinylation/derivatization
Electrophiles: Imidates, CDI-activated carboxamidine precursors, chloroformamidines, and carbamimidoyl chlorides.
Solvents: Alcohols (MeOH/EtOH) or polar aprotics (DMF, MeCN) with base scavenging as needed.
Temperature/time: 25–80 °C, 2–16 h common; monitor by LC/MS or TLC.
Additives: Triethylamine or carbonate bases can assist where HCl is released; phase-transfer catalysts aid heterogeneous systems.
Workup/purification
Acid–base toggling can simplify isolation: convert to a crystalline guanidinium salt (e.g., HCl) for filtration, then regenerate the free base if required.
Notes
Exclude CO2 to prevent formation of guanidinium carbonate which reduces effective basicity and complicates stoichiometry.
Avoid strong oxidants; handle under dry conditions for reproducibility.
Safety and Handling
Item-specific hazard fields were not provided. Always consult the SDS for authoritative safety information.
GHS/Classification (item-specific): Not specified for this item; refer to SDS.
Typical hazards (general chemistry knowledge)
Strong organic base; can be corrosive to skin and eyes; causes severe irritation to respiratory tract if dust is inhaled.
Hygroscopic and CO2-absorbing; exothermic dissolution in water possible at high loadings.
Personal protective equipment (PPE)
Use lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles; handle powders in a fume hood to avoid dust inhalation.
Incompatibilities (general)
Acids (vigorous neutralization, heat release), acid chlorides/anhydrides (salt formation, possible exotherm), strong oxidizers, carbon dioxide (forms guanidinium carbonate), and prolonged exposure to moist air.
Handling tips
Work rapidly with minimal air exposure; keep containers tightly closed with desiccant.
If preparing solutions, add solid to solvent with stirring; control heat evolution.
First-aid overview (general)
Skin/eyes: Immediate decontamination with copious water for ≥15 min; remove contaminated clothing; seek medical evaluation.
Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; obtain medical advice.
Deferral: For exact pictograms, signal word, and H-statements, Not specified for this item; refer to SDS.
Solvent Selection
Guanidine is a highly polar, strongly basic solid. Solvent choice is driven by intended role (base, nucleophile, or precursor) and required medium.
Polarity/miscibility profile (literature)
Very soluble in water; forms strongly basic solutions.
Soluble in polar protic solvents (MeOH, EtOH); moderately soluble in some polar aprotics when water/alcohol is present.
Poorly soluble in nonpolar media (alkanes, aromatics) as the free base.
Typical use scenarios
As an aqueous base: water or water/alcohol mixtures for neutralizations, condensations, or phase-transfer contexts.
In organic synthesis: MeOH/EtOH or polar aprotics with a co-solvent alcohol to enhance dissolution.
Practical tips
Avoid CO2-rich atmospheres; prepare solutions under inert gas where feasible to limit guanidinium carbonate formation.
If solubility is limiting, consider forming a transient salt with a volatile acid (e.g., HCl) and then neutralize in situ; or use a more soluble substituted guanidine.
Comparison (general guidance)
Versus inorganic bases (K2CO3, NaOMe): Guanidine offers higher basicity in protic media without introducing metal cations but is more air-sensitive (CO2 uptake).
Versus superbases (DBU, TBD): Guanidine is less basic/catalytically active but is simpler, less sterically demanding, and can serve as a precursor to tailored guanidines.
Storage and Reconstitution
Storage (item-specific)
Storage Conditions: Room temperature (per Product Data).
Container: Tightly sealed, moisture- and CO2-resistant packaging recommended.
Stability and handling (literature/general)
Guanidine is hygroscopic and absorbs CO2 from air to form guanidinium carbonate/bicarbonate; limit headspace exposure and consider desiccant and inert gas backfill.
Avoid prolonged exposure to acids and oxidizers; store away from incompatible materials.
Reconstitution/preparation of solutions
Water or lower alcohols (MeOH/EtOH) are preferred for stock solutions; add solid gradually with stirring due to potential heat evolution.
Prepare solutions fresh where possible; if storage is necessary, use tightly sealed containers under inert atmosphere at ambient temperature. For aqueous stocks, microbial growth can be minimized by sterile filtration and clean technique.
Shipping
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Research use note
For research use only. Not for human or veterinary use.
Structure and Identity
Brief overview: Guanidine is the parent, unsubstituted guanidino compound — a highly basic, planar, three‑nitrogen functionality widely used as a building block for guanidinium derivatives.
Item-specific identifiers (Product Data)
SKU: G610749
Product Name: guanidine
CAS: 113-00-8
InChIKey (as provided): 464315
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identifiers and formula (for reference; not item specifications)
Functional group: Guanidine (carboxamidine) core, one carbon doubly bonded to an imine nitrogen and singly bonded to two amino nitrogens.
Hybridization & geometry: Central carbon is sp2; three nitrogens enable extensive resonance, distributing positive charge in the conjugate acid (guanidinium).
Protonation: Strong base; readily forms guanidinium cation under acidic to neutral conditions.
2D description: Central C(=NH)–NH–NH framework; planar CN3 unit due to delocalization; no stereocenters; no ring systems.
Tautomerism: Amino–imine tautomers interconvert; resonance-stabilized canonical forms dominate.
Synthetic Utility
Strategic value stems from dual functionality: a strong Brønsted base and a nitrogen-rich nucleophile capable of delivering guanidinium units.
Key transformations (literature/general)
Guanidinylation: Reaction with activated carboxamidine equivalents (imidates, chloroformamidines) or CDI-activated species to yield mono- or disubstituted guanidines.
Biguanide formation: Condensation with cyanamide or dicyandiamide to extend the guanidino framework.
Cyclocondensations: Assembly of triazines, pyrimidines, and other N-heterocycles from bifunctional electrophiles.
Base-mediated steps: Facilitates O- to N-acyl transfer, Michael additions of modestly acidic pronucleophiles, and ester interchange under protic conditions.
Retrosynthetic role
Serves as a convergent synthon to introduce the highly basic, H-bond-donating guanidinium pharmacophore late in synthesis to avoid incompatibility with earlier steps.
Selectivity and protection
Multiple N-sites require control of mono- vs di-substitution; utilize protecting groups (e.g., Boc on amines) or selective activation (imidates vs acid chlorides) to dictate substitution patterns.
Practical notes
Employ inert atmosphere to prevent carbonate formation that can attenuate reactivity.
Use polar protic co-solvents to increase dissolution and reaction rate when needed.
Target Specificity
Not applicable. This product is a small molecule base/building block, not a biological targeting reagent or antibody. No antigen/epitope or species reactivity is associated with this item.
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