Potassium cyanate-C , CAS No.69545-33-1

CAS: 69545-33-1 Cat. No.: P1449908 Formula: ₁₃CKNO Peso molecolare: 82.11

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

Potassium cyanate- 13 C is the 13 C labeled Potassium cyanate.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Nomi e identificatori

Peso molecolare

82.11

Application Protocols

Not applicable. No tested bioassay formats (WB, IHC, IF, FC, etc.) are provided for this inorganic salt. For use in synthesis or in vitro chemical modification (e.g., carbamylation studies), consult standard organic/bioconjugation protocols and optimize conditions for your substrate (see Reaction Conditions tab).

Biological Roles

No biological function is claimed for this product; it is supplied strictly for research use.

General biochemical context (literature/general):

• The cyanate anion participates in carbamylation chemistry, modifying primary amines (e.g., N-termini or lysine residues) to form carbamylated derivatives in vitro. This reaction is used to study protein function, structure, and to create defined chemical modifications.
• In aqueous systems, cyanate is in equilibrium with isocyanic acid (HNCO), whose reactivity toward nucleophiles under controlled pH allows targeted modification experiments.
• Isotopically labeled variants (e.g., 13C at the cyanate carbon) enable tracer studies by NMR or MS for tracking carbamyl groups in peptides, proteins, and metabolites.

Notes:

• Reaction conditions (pH, temperature, ionic strength) strongly influence the rate and selectivity of carbamylation in biological matrices. Buffer choice is critical to avoid unintended side reactions (see Buffer Applications and Reaction Conditions tabs).
• No physiological, nutritional, or therapeutic roles are implied; for laboratory research only.

Buffer Applications

Potassium cyanate is not a buffering agent and is not typically used to prepare buffer systems.

Relevant laboratory use (literature/general):

• When used for protein or peptide carbamylation, experiments are typically conducted in existing buffers (e.g., phosphate, borate, carbonate) where pH is carefully controlled to modulate cyanate/HNCO speciation.
• Practical tips:
  • Avoid strongly acidic buffers to minimize HNCO volatilization and excessive, nonselective carbamylation.
  • Use freshly prepared cyanate solutions in chilled, neutral-to-mildly basic buffers; verify pH before and after addition.
  • Consider buffer components lacking primary amines (avoid Tris, glycine) if unintended scavenging of cyanate is a concern.

If a buffer recipe is required for a specific protocol, consult primary literature and validate conditions for the target biomolecule.

Green Alternatives

Context: Potassium cyanate is used primarily as a carbamylating reagent and precursor to isocyanates/ureas. While it avoids phosgene, it still presents toxicity concerns (HNCO release) and challenges in aqueous waste.

Greener or safer alternatives (literature/general):

• CDI (1,1′-carbonyldiimidazole):

  • Pros: Phosgene-free, solid, comparatively easier handling; generates imidazole byproduct.
  • Cons: Less atom-economical; moisture sensitive; different reactivity/selectivity than cyanate.

• Organic carbonates (e.g., dimethyl/diethyl carbonate):

  • Pros: Lower toxicity, biodegradable profile; useful for carbamoylation under catalysis.
  • Cons: Typically require higher temperatures/stronger catalysts; may not directly yield isocyanates.

• Urea/activated urea derivatives:

  • Pros: Accessible and inexpensive; benign byproduct profiles.
  • Cons: Limited scope without activating agents; may not provide isocyanates directly.

• Polymer-supported carbodiimides or green coupling systems (e.g., EDC in water for select cases):

  • Pros: Aqueous compatibility; simplified workup.
  • Cons: Scope limitations and potential for side reactions; not ideal for installing a labeled carbonyl unless isotopically enriched reagent is used.

Comparison snapshot (general):

• Potassium cyanate: phosgene-free route to isocyanates/ureas; aqueous solubility; toxicity concerns; isotopic labeling straightforward.
• CDI/Carbonates: safer handling, fewer acute hazards; may require different conditions and won’t natively install cyanate-derived labeling unless isotopically enriched CDI/carbonate is used.

Conclusion: For isotopic labeling at the carbonyl carbon, 13C-cyanate is often the most direct route; where labeling is not required, consider CDI or dialkyl carbonates for greener profiles.

Pharmaceutical Uses

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

Context (literature/general):

• Isotopically labeled cyanate salts can be used to prepare 13C-labeled ureas, carbamates, and isocyanates that serve as analytical standards or tracers in nonclinical development, metabolite identification, and in vitro ADME investigations.
• In process R&D, cyanate routes may provide phosgene-free access to isocyanates/ureas for intermediate synthesis. Suitability for GMP or clinical manufacturing would require dedicated quality, residuals, and impurity controls not implied here.

Note: No therapeutic, diagnostic, or clinical claims are made. For any regulated use, obtain full quality documentation and assess compliance independently.

Physical Properties

Item-specific properties provided: none besides storage.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Literature/general: potassium cyanate is a high-melting, stable ionic solid; MP typically >300 °C with possible decomposition.)
• Boiling point: Not applicable for an ionic salt; decomposition occurs before boiling (literature/general).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet. (Literature/general: readily soluble in water; low solubility in nonpolar solvents; soluble in polar aprotic media such as DMF/DMSO.)
• LogP: Not applicable to inorganic salts in the usual sense (literature/general).
• pKa: Not applicable; the cyanate anion is the conjugate base of isocyanic acid (HNCO), which is weakly acidic (literature/general).
• Refractive index: Not applicable to a solid salt in bulk; not typically reported (literature/general).

Notes:

• Numeric specifications (e.g., exact solubility, MP range) are not provided for this catalog item and should be taken from the item-specific CoA/Spec Sheet if required for QC or method development.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet. For isotopically labeled salts, the CoA typically lists % isotopic enrichment (e.g., 13C%), chemical purity, water content, and residual inorganic limits.

Guidance (general):

• Isotopic materials: The most critical quality attributes are (1) isotopic enrichment at the specified carbon, (2) chemical purity (absence of cyanide, carbonate, thiocyanate, or biuret contaminants), (3) water content, and (4) counter-ion identity and assay.
• Analytical reagent vs. research grade: Analytical grades may control trace metals/UV-absorbing impurities for spectroscopic work; research grade emphasizes chemical purity for synthesis and labeling. Since no grade is specified here, verify suitability with the CoA for sensitive applications (e.g., NMR tracers, MS standards).
• Stabilizers: None indicated for this item. If stabilizers or anti-caking agents are used, they will be listed on the CoA/Spec Sheet; absence cannot be assumed.

Practical notes:

• For quantitative isotope tracing or NMR, request the exact isotopic enrichment and any lot-specific QC (e.g., 13C NMR confirmation, HRMS). If UV-transparency is relevant, obtain a UV cut-off profile; otherwise, assume only general inorganic-salt background.

Reaction and Applications

Applications (literature/general for potassium cyanate; extendable to 13C-labeled material for tracer synthesis):

• Formation of substituted ureas from primary amines and KOCN. The amine reacts with the cyanate to generate an isocyanate or carbamylated intermediate, which then affords the urea after workup. Useful for installing a 13C-labeled carbonyl in the urea motif.
• Preparation of alkyl isocyanates from alkyl halides and KOCN in polar solvents, often with phase-transfer catalysis. The O-cyanate pathway can rearrange to isocyanate under thermal or catalytic conditions, providing access to labeled isocyanates without phosgene.
• Synthesis of carbamates (urethane esters) by reaction of cyanate-derived isocyanates with alcohols. Valuable for making 13C-labeled carbamates for mechanistic or metabolic studies.
• Protein carbamylation/chemical modification studies: cyanate can carbamylate N-termini and lysine side chains in vitro; 13C labeling facilitates MS/NMR tracking of modified residues.
• Formation of hydantoins and related heterocycles via condensation with α-amino nitriles or under conditions where cyanate serves as a carbamylating agent (route- and substrate-dependent).

Practical tips:

• Maintain low moisture to prevent hydrolysis and preserve isotopic integrity.
• pH control is critical: acid catalysis increases HNCO formation; mild basic conditions favor controlled carbamylation.
• For nucleophilic substitutions with poor solubility, use PTC (e.g., quaternary ammonium salts) to shuttle OCN− into organic phases.
• For analytical incorporation, confirm isotopic placement by 13C NMR and HRMS; monitor for isotopic dilution if aqueous workup is prolonged.

Reaction Conditions

General guidance from literature (not item-specific; optimize per substrate):

• Urea formation from primary amines:

  • Solvent: Water, ethanol, or polar aprotic (DMF/DMSO).
  • Conditions: 0–60 °C; neutral to mildly basic pH if aqueous. Stoichiometry near 1:1 to 1.2:1 (KOCN:amine). Reaction times: 0.5–16 h depending on substrate.
  • Workup: Quench carefully; isolate urea by evaporation and crystallization or extraction if organic-soluble.

• Alkyl isocyanate generation from alkyl halides:

  • Solvent: Acetone or acetonitrile; optional water/organic biphasic with PTC (e.g., tetrabutylammonium bromide).
  • Conditions: 20–70 °C; 1–3 equiv KOCN; reaction times 2–24 h.
  • Trapping: Add alcohols or amines to convert isocyanate to carbamate/urea in situ.

• Carbamate synthesis via isocyanate trapping:

  • Solvent: Anhydrous aprotic (DCM, THF, MeCN) after generating the isocyanate.
  • Conditions: 0–25 °C for trapping; base (e.g., Et3N) can neutralize HCl or adventitious acid.

• Protein carbamylation (analytical studies):

  • Medium: Buffered aqueous solution free of primary amine buffers (avoid Tris).
  • Conditions: 0–25 °C; pH 7.2–9.0 depending on selectivity; reaction times from minutes to hours.

Yields: Substrate-dependent; aliphatic amines to ureas commonly give moderate to high isolated yields; benzylic halides to isocyanates are typically competent under PTC. Always confirm isotopic incorporation (13C NMR/HRMS) when labeling.

Safety and Handling

Authoritative safety data must be taken from the SDS for this exact SKU.

Item-specific hazard data provided: none.

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

General safety considerations for cyanate salts (literature/general):

• Hazards: May cause irritation to skin, eyes, and respiratory tract. Cyanate salts are generally less acutely toxic than cyanides, but can release isocyanic acid (HNCO) under acidic or high-temperature conditions; HNCO is corrosive and toxic by inhalation.
• Incompatibilities: Avoid strong acids (risk of HNCO formation), strong oxidizers, and prolonged exposure to moisture/CO2 (hydrolysis/neutralization). Do not mix with ammonium salts unless intended, as equilibria with carbamylating species can occur.
• Special risks: Moisture can promote slow decomposition and loss of isotopic integrity in labeled materials. Handle powders to minimize dust generation.
• Recommended PPE: Lab coat, safety glasses or face shield, nitrile gloves (change regularly), and use of a fume hood for weighing, solution prep, and reactions.
• First aid (overview; defer to SDS): Inhalation—move to fresh air; seek medical attention. Skin/eye—rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention. Ingestion—rinse mouth; do not induce vomiting; seek immediate medical attention.
• Spill response: Avoid dust and moisture; collect with minimal water; place in compatible container for disposal per local regulations.

Storage from Product Data:

• Store at −20 °C. Shipments: Ice chest + ice pads (keep cold). Keep tightly closed, dry, and protected from acids; consider inert-atmosphere/desiccant storage for isotopic integrity.

Solvent Selection

This product is an inorganic salt; solvent choice is governed by ionic solubility and reaction compatibility.

General solvent behavior (literature/general):

• Polarity class: Highly polar/ionic; dissolves best in water and strongly polar aprotic solvents (DMSO, DMF, NMP). Limited to negligible solubility in nonpolar and moderately polar organic solvents (e.g., ethers, hydrocarbons, esters, chlorinated solvents).
• Dielectric constant considerations: Solvents with εr > 30 (water, DMSO, DMF) substantially enhance dissolution and ionic reactivity.
• Protic vs. aprotic: Water and lower alcohols can solubilize KOCN but may also participate in side reactions (carbamylation/hydrolysis). For preparing organic isocyanates via cyanate displacement, acetone or acetonitrile are often used with phase-transfer conditions to suspend/dissolve the salt (literature/general).

When to choose which solvent:

• Aqueous carbamylation studies (protein or small-molecule): Use buffered aqueous media with controlled pH (typically neutral to mildly basic to limit HNCO formation) and low temperatures.
• Synthesis of ureas/carbamates: Use polar aprotic solvents (DMF, DMSO, MeCN) to maximize nucleophilicity; carefully control water content.
• Alkyl isocyanate formation from alkyl halides: Acetone/MeCN with phase-transfer catalysts can improve rates (literature/general).

Comparison (general):

• Water: safest handling and highest salt solubility; may promote hydrolysis.
• DMF/DMSO: high solubility, good for homogeneous reactions; removal can be more challenging.
• MeCN/acetone: facilitate SN reactions under PTC; solubility is lower but sufficient in presence of PTC.

Storage and Reconstitution

• Storage (from Product Data): Store at −20 °C.
• Shipping (from Product Data): Shipped in ice chest with ice pads. Keep cold on receipt; minimize temperature excursions.

Handling and stability (general):

• Keep container tightly closed, dry, and protected from light and acidic vapors to prevent formation of isocyanic acid and hydrolysis. Consider storage under inert gas with desiccant to preserve isotopic integrity of labeled material.
• Avoid repeated warming/cooling cycles; stage working aliquots to limit freeze–thaw and moisture ingress.

Reconstitution (general guidance):

• Prepare solutions freshly in dry, oxygen/CO2-free water or anhydrous polar aprotic solvents (e.g., DMSO, DMF) as required by application.
• Typical stock concentrations range from millimolar to low molar depending on solubility and use; filter sterilize (0.2 μm) if working in biological systems.
• Store solutions at low temperature (e.g., 2–8 °C for short term; −20 °C for longer term) in sealed vials; verify stability and isotopic integrity by analytical methods (e.g., 13C NMR, LC–MS) before critical experiments.

Disposal: Collect unused solutions and wastes as cyanate-containing inorganic waste per institutional and local regulations; do not acidify waste streams.

Structure and Identity

• Item: Potassium cyanate-C (likely 13C-labeled potassium cyanate; isotopic enrichment not specified for this item)
• CAS: 69545-33-1
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Note: empirical composition corresponds to K+, O, C, N for potassium cyanate; isotope details depend on labeling.)
• 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.

Structural features (general chemistry knowledge):

• Inorganic salt composed of a potassium cation (K+) and the cyanate anion (OCN−). In an isotopically labeled "-C" version, the carbon of the O–C≡N unit is typically enriched in 13C (literature/general).
• Functional group: cyanate (–O–C≡N), featuring a cumulene/isonitrile-like heterocumulene motif with significant resonance between O–C≡N and O−–C≡N↔O=C=N− (literature/general).
• 2D description: a linear anion O–C≡N paired with K+; the carbon atom is between oxygen (single or partial double bond by resonance) and nitrogen (triple or partial double bond by resonance). No stereocenters (literature/general).

Synthetic Utility

Functional group reactivity (literature/general):

• Cyanate anion (OCN−) is an ambident nucleophile. It reacts with electrophiles to generate O-cyanate intermediates that can rearrange to isocyanates (R–N=C=O), which are versatile in forming ureas, carbamates, thiocarbamates, and urethanes.
• With primary amines, KOCN affords N,N′-disubstituted ureas after carbamylation and coupling; particularly useful for installing a 13C-labeled carbonyl.
• With alkyl halides (especially benzyl and activated secondary centers), KOCN can furnish alkyl isocyanates under suitable conditions; these then react with nucleophiles (amines/alcohols) in situ.

Strategic uses:

• Rapid access to 13C-labeled urea motifs common in medicinal chemistry scaffolds (e.g., urea-linked kinase inhibitors) for tracer synthesis and analytical support.
• Synthesis of carbamate protecting groups and labeled linkers for bioconjugation.
• Entry to hydantoin and allophanate frameworks under condensative conditions.

Practical considerations:

• Control moisture and avoid acidic media to prevent hydrolysis and HNCO evolution.
• For SN reactions in organic media, phase-transfer catalysis or crown ethers can enhance OCN− nucleophilicity and solubility.
• Verify isotopic incorporation via 13C NMR; quantify enrichment against standards to ensure tracer fidelity.

Target Specificity

Not applicable. This product is a small-molecule inorganic salt, not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species specificity is associated with this item.