2-Propynylammonium iodide - ≥99.5%(4 Times Purification) , CAS No.205817-86-3

CAS: 205817-86-3 Cat. No.: P491889 Formula: C₃H₆NI Peso molecolare: 182.99

GRADE & PURITY ≥99.5%(4 Times Purification)

Synonyms

PNAI

Storage

Protected from light,Room temperature,Argon charged

Shipped In

Normal

Specifications

Sinonimi

PNAI

Specifiche e purezza

≥99.5%(4 Times Purification)

Condizioni di conservazione di stoccaggio

Protected from light,Room temperature,Argon charged

Spedito in

Normal

Purezza

≥99.5%(4 Times Purification)

Nomi e identificatori

• Peso molecolare: 182.99
• Reaxy-Rn: 3669067
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3669067&ln=

Proprietà chimiche e fisiche

• Solubilità: Soluble in DMF, DMSO et al
• Sensibilità: Moisture sensitive；air sensitive；light sensitive

Application Protocols

No assay-specific protocols are provided for this item. For materials applications, typical practices include:

• Perovskite film surface treatment (literature, general)

  • Prepare a 1–10 mg/mL solution in anhydrous IPA or MeOH under inert atmosphere.
  • Filter through a 0.2 µm PTFE membrane.
  • Spin-coat onto freshly prepared perovskite films (e.g., 3000 rpm, 20–30 s), then anneal at 80–100 °C for 5–10 min. Optimize concentration and contact time to avoid over-extraction of A-site cations.

• Conversion to free amine for synthesis

  • Neutralize an aliquot with Et3N, extract into ether, and use directly in CuAAC or coupling reactions as outlined under Reaction Conditions.

For analytical verification

• Monitor modifications by XPS (iodide/amine surface signatures), GIWAXS (2D layering), or contact-angle changes. For small-molecule synthesis, confirm by NMR/HRMS.

Always tailor parameters to your specific substrate, equipment, and safety constraints.

Biological Roles

This product is intended for research use only and is primarily a materials/synthetic reagent. It does not have established biological roles as a metabolite or cofactor.

General chemistry context (literature; not item-specific)

• Primary ammonium species are conjugate acids of primary amines; in biological systems, analogous small amines can participate in acid–base equilibria and ionic interactions. However, 2-propynylammonium is not a known endogenous metabolite.
• The terminal alkyne provides a bioorthogonal handle in chemical biology when converted to the free base (propargylamine), enabling conjugation to azides via CuAAC. Such applications are method-oriented rather than a biological role of the salt itself.

No clinical or therapeutic claims are made or implied.

Buffer Applications

Not typically used as a buffer component. Primary ammonium salts have conjugate acid pKa values around 10–11 (literature, propargylammonium expected in this range), placing them outside the optimal buffering range for most biochemical assays.

Practical notes (if considering pH adjustments)

• The salt can transiently acidify basic media upon dissolution, but it lacks a suitable acid/base pair with appreciable capacity near neutral pH.
• For buffering near physiological pH, choose dedicated systems (e.g., phosphate, HEPES, MOPS). For alkaline buffering, borate or carbonate systems are more appropriate.

Green Alternatives

Assessment and options (literature-based; balance performance vs sustainability)

• Solvent footprint

  • Prefer water, ethanol, or isopropanol for preparing treatment solutions when compatible with your substrate/system, reducing reliance on high-toxicity aprotics (DMF, DMSO). Dry alcohols can often substitute for DMF in film post-treatments.

• Counterion and precursor choices

  • Chloride or bromide analogs (2-propynylammonium chloride/bromide) may offer lower persistence concerns for iodide in some waste streams, but may not match iodide’s compatibility with iodide-based perovskites. Selection should align with the halide chemistry of the target lattice.

• Process intensification

  • Mechanochemical or solvent-minimized mixing for salt-to-ink blending can reduce solvent use in ink preparation (ball milling or mortar-and-pestle under inert conditions).
  • Spin/dip-coating with antisolvent-free crystallization strategies (substrate heating, gas quenching) reduces halogenated antisolvents.

• Comparative snapshot (general)

  • 2-Propynylammonium iodide vs free propargylamine: the salt is less volatile and easier to handle; the free base avoids halide waste but is more hazardous (flammability, volatility). Choose based on EHS and process compatibility.

Note: Always evaluate green substitutions with small-scale trials to confirm film quality, device performance, and stability tradeoffs.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; refer to CoA/Spec Sheet. This product is supplied for research use only.

General information (literature context)

• Simple ammonium iodides are occasionally used in formulation research as ionic additives, but 2-propynylammonium iodide is not a standard excipient.
• If the free base (propargylamine) is needed in pre-formulation chemistry, ensure conversion from the iodide salt is quantitative and that residual iodide is controlled if it could affect stability or compatibility.

No medical or clinical claims are made.

Physical Properties

Item-specific physical properties

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

Literature/general expectations for this salt (reference values; not item specifications)

• Physical state: typically a crystalline, hygroscopic ionic solid (literature, typical of small primary ammonium iodides).
• Solubility: highly soluble in water and polar protic solvents (e.g., methanol, ethanol); moderate in DMF/DMSO; negligible in nonpolar solvents (literature, general behavior of ammonium halides).
• Acid–base: conjugate acid of propargylamine; expected pKa of the conjugate acid ~10–11 (literature range for primary aliphatic ammonium ions; propargylamine pKaH reported ~10.6–11, source-general literature).
• Partitioning: expected very low logP in the protonated (salt) form; partitions to aqueous phase (literature, general ionic salt behavior).
• Volatility: non-volatile; no meaningful vapor pressure under ambient conditions (general for ammonium salts).

Not determined for this specific item (consult CoA/SDS for authoritative values)

• Melting point, decomposition temperature, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Context for typical grades (general guidance)

• Research grade: Suitable for most synthetic and materials R&D. Typical controls include halide content confirmation, residual solvents, and water content (Karl Fischer). Low metals may be desirable for optoelectronic applications, but limits must be stated on the item’s CoA to be considered specifications.
• Electronic/materials grade (general): Emphasizes low alkali/transition metals and halide purity; beneficial for perovskite and thin-film work. UV–Vis baseline and particulate control may also be noted.
• Stabilizers: None are typically added to simple ammonium iodide salts. Any stabilizer, if present, must be listed on the CoA/Spec Sheet (none specified here).

What to verify on receipt (best practices)

• Identity: 1H/13C NMR in D2O or DMSO-d6 (signals for –CH2–NH3+, terminal alkyne proton ~2–3 ppm? Note: terminal alkyne in salt form can shift), ATR-IR (C≡C stretch ~2100–2140 cm−1; NH3+ bands).
• Water content and hygroscopicity: Check KF if your application is moisture-sensitive.
• Residual inorganic impurities: Ion chromatography for halides; ICP-MS if low-metal requirements apply.

Note: Unless explicitly listed on the CoA, numerical values (water ppm, metals, UV cutoff) are not specifications for this item.

Reaction and Applications

Materials science applications (aligned with category)

• Organic ammonium iodides are widely used as spacers, passivating agents, or A-site cations in halide perovskite films. The terminal alkyne in 2-propynylammonium can offer additional binding or post-functionalization handles on perovskite surfaces (literature concept). Typical uses include:
  • Post-treatment of 3D perovskite films to passivate surface defects via ammonium–halide interactions.
  • Formation of quasi-2D/2D perovskite layers with organic cation interlayers; the small cation size can modulate dimensionality and optoelectronic properties.
  • Additive engineering in precursor inks to influence crystallization kinetics and grain boundaries.

Synthetic chemistry applications (using the salt as an amine source)

• Base-liberation to propargylamine (free base) enables:
  • CuAAC “click” reactions of terminal alkyne with azides to form 1,2,3-triazoles (often CuSO4/sodium ascorbate, RT–50 °C, aqueous/organic media).
  • Amide formation with activated carboxylic acids (EDC/HOBt or HATU/DIPEA in DMF/MeCN).
  • Reductive amination onto carbonyls (NaBH3CN/NaBH(OAc)3) exploiting the primary amine.
  • N-protection (Boc, Cbz) to facilitate downstream alkyne chemistry (Sonogashira, hydroboration–oxidation after suitable transformations).

Practical tips

• To use in non-aqueous synthesis, first neutralize the salt with a slight excess of organic base (e.g., Et3N) and extract the free amine into an organic phase; dry and titrate if necessary.
• For materials processes, maintain low water content and exclude oxygen/light to minimize iodide oxidation (brown I2 formation).

Reaction Conditions

General conditions (literature guidance; optimize per system)

• Liberation of free base from the iodide salt

  • Dissolve the salt in water, MeOH, or MeCN; add 1.1–1.5 equiv of base (e.g., Et3N, Na2CO3). Extract the free amine into Et2O or MTBE, dry (Na2SO4), and use immediately or store cold under inert gas.

• CuAAC (click) to triazoles

  • Solvent: t-BuOH/H2O (1:1), DMSO/H2O, or neat water.
  • Catalyst: CuSO4·5H2O (1–5 mol%) + sodium ascorbate (5–20 mol%) to generate Cu(I) in situ; optional ligands (TBTA/THPTA) 5–20 mol%.
  • Temperature/time: RT to 50 °C; 0.5–12 h depending on substrates.
  • Typical outcomes: high regioselectivity to 1,4-triazoles; often >80% isolated yields with clean substrates.

• Amide coupling (to acylate the amine)

  • Solvent: DMF, NMP, or MeCN; base: DIPEA (2–3 equiv).
  • Coupling reagents: HATU, HBTU, or EDC/HOBt.
  • Temperature: 0 °C to RT (sensitive substrates) up to 40 °C; 1–6 h.

• Reductive amination

  • Solvent: MeOH/CH2Cl2 or MeOH/THF; additive: AcOH (catalytic) for imine formation.
  • Reductant: NaBH3CN (1.2–2.0 equiv) or NaBH(OAc)3 in DCE/AcOH.
  • Temperature: 0–25 °C; 1–16 h.

• Alkyne deprotonation/alkylation

  • Protect the amine (e.g., Boc) first; base: NaH or LDA in THF at 0 to −78 °C; then add electrophile (R–X). Quench carefully and deprotect as needed.

Note: Conditions are representative literature practices; adjust stoichiometry and purification to substrate scale and sensitivity.

Safety and Handling

Item-specific handling

• Storage per Product Data: store at room temperature, protected from light, under argon (inert atmosphere).
• Shipping: Normal ambient shipment.

GHS and hazard data

• Signal Word / H-Statements / Pictograms / Classification: Not specified for this item; refer to SDS for authoritative information.

General safety guidance for small organic ammonium iodides (literature; not item-specific)

• Hazards: May be irritating to skin, eyes, and respiratory tract. Iodide salts can be mildly hygroscopic. Avoid dust formation and inhalation.
• Incompatibilities: Strong bases will liberate the free amine (propargylamine), which is flammable and more volatile; strong oxidizers may react with iodide or the organic cation. Avoid contact with nitrites in acidic media (risk of nitrosation for primary amines if freed from salt).
• Light sensitivity: Iodide can slowly oxidize under light/air to iodine; protect from light and air exposure as directed.
• Peroxide formation: Not a peroxide-forming solvent; no specific peroxide risk.
• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to control dust.
• First aid (summary; defer to SDS): If inhaled—fresh air; skin—wash with soap/water; eyes—rinse with water for several minutes; ingestion—rinse mouth and seek medical advice. Provide SDS to medical personnel.

Waste and spills

• Spill response: Avoid dust, sweep with minimal agitation, collect for disposal. Rinse area with water.
• Disposal: Dispose as organic salt/halide-containing waste according to institutional and regional regulations.

Solvent Selection

Practical guidance for handling as a reagent and for preparing solutions

• Polarity class: Ionic salt; best handled in highly polar solvents.
• Recommended solvents (literature/general):
  • Water: typically freely soluble; ideal for stock solutions when using the salt form directly.
  • Alcohols (MeOH, EtOH): good solubility; convenient for thin-film deposition additives or homogeneous catalysis inputs.
  • DMSO, DMF: good to excellent solubility; useful for coupling chemistry and for processing in materials science.
  • Acetonitrile: moderate solubility; may require slight warming/sonication.
• Poor solvents: Ethers, hydrocarbons, chlorinated nonpolar solvents (hexane, toluene, CH2Cl2) show minimal solubility for the salt; use the free base (propargylamine) instead if nonpolar media are required.

When to use salt vs free base

• Use the iodide salt when ionic character is needed (e.g., as an A-site organic cation in halide perovskite formulations or as an additive in polar media).
• Convert to the free base with a stoichiometric base (e.g., triethylamine, Na2CO3) to access propargylamine for reactions in less polar or basic media.

Processing notes (materials focus)

• Film deposition: For perovskite surface treatments, prepare 1–20 mg/mL solutions in IPA, MeOH, or DMF; filter (0.2 µm PTFE) before spin/dip-coating (literature practice; optimize per system).
• Water-sensitive systems: Dry polar aprotic solvents and handle under inert gas to match the product’s storage guidance.

Storage and Reconstitution

Item-specific storage (from Product Data)

• Store protected from light, at room temperature, under argon (argon charged).
• Shipped at ambient conditions (Normal).

General handling and reconstitution guidance

• Hygroscopicity: As with many ammonium iodides, minimize atmospheric exposure. Open under inert gas when possible. Reseal promptly.
• Solid handling: If clumping occurs due to moisture uptake, gently dry under vacuum at ambient temperature before weighing. Avoid heating in air to prevent iodide oxidation to iodine.
• Solution preparation: Use dry, oxygen-free solvents for moisture/air-sensitive applications. For aqueous stocks, prepare fresh and store in amber vials to limit light exposure.
• Inert atmosphere: Maintain argon or nitrogen blanket for long-term stability, consistent with the product’s storage guidance.
• Freeze–thaw: Not typically applicable to solids. For solutions, aliquot and store at low temperature (e.g., 2–8 °C) if compatible; avoid repeated freeze–thaw cycles.

Shelf-life and specifications

• Specific shelf-life, stabilizers, and impurity limits: Not specified for this item; refer to CoA/Spec Sheet.

Research use

• For research use only. Not for human or animal consumption or clinical use.

Structure and Identity

Brief description: 2-Propynylammonium iodide is the protonated ammonium salt of propargylamine (prop-2-yn-1-amine), paired with iodide as the counter-anion. The cation bears a terminal alkyne and a primary ammonium center.

• Item-specific identifiers (from Product Data)

  • CAS: 205817-86-3
  • SKU: P491889
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • CID: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity details (for reference; not item specifications)

  • Synonym: Propargylammonium iodide; Prop-2-yn-1-ylammonium iodide
  • Likely overall formula (salt): C3H8NI (literature, based on [HC≡C–CH2–NH3]+ I−)
  • Approx. formula mass: ~185.0 g/mol (literature calculation)
  • Representative SMILES (salt, literature): C#CC[NH3+].[I-]

• Structural features (general description)

  • Functional groups: terminal alkyne (–C≡CH) on a primary ammonium (–CH2–NH3+).
  • Ionic character: discrete organic cation paired with iodide anion.
  • 2D description: a three-carbon chain with a triple bond between C1–C2; C3 is methylene bound to a protonated nitrogen (tetra-coordinate N bearing three hydrogens), with iodide as the counter-ion.
  • Stereochemistry: none (achiral, no stereocenters).

Synthetic Utility

Functional group set and value

• Dual reactivity handle: primary ammonium (as salt) convertible to primary amine (nucleophile) plus a terminal alkyne (weak acid, nucleophile after deprotonation, and dipolarophile in cycloadditions).

Key transformations after base-liberation to propargylamine (literature)

• Click chemistry: Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) to 1,4-disubstituted triazoles; ligands such as TBTA or THPTA improve kinetics in water/tert-butanol.
• Amide/urea formation: coupling with carboxylic acids (EDC/HOBt, HATU) or with isocyanates/carbonyl diimidazole to give ureas/carbamates.
• Reductive amination: reaction with aldehydes/ketones followed by NaBH3CN or NaBH(OAc)3.
• N-protection strategies: Boc, Cbz, Fmoc to control chemoselectivity during alkyne manipulations.
• Metalation/alkynyl chemistry: deprotonation of the terminal alkyne (e.g., with NaH) followed by alkylation or addition to electrophiles; ensure the amine is protected to avoid acid–base neutralization.

As an ionic building block (materials)

• Incorporation as an organic A-site cation in Pb/Sn halide perovskites or as a passivation additive to reduce nonradiative recombination at grain boundaries (literature practice with organic ammonium iodides). The alkyne may allow post-deposition click-style grafting onto treated surfaces.

Target Specificity

Not applicable. This product is a small-molecule salt, not a biological macromolecule or affinity reagent. No antigen/epitope specificity, clone, or isotype information applies.