This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
External Descriptors
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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
No item-specific tested application protocols are provided for this product; refer to CoA/Spec Sheet.
General usage guidance (literature-based, for small-molecule reagents):
For amide coupling: dissolve tridecan-7-amine and the carboxylic acid (1.0 eq each) in dry DCM or DMF; cool to 0 °C; add HATU (1.2 eq) and DIPEA (2.5 eq); stir 1–2 h at 0–5 °C then warm to rt and monitor by TLC/LC–MS. Quench with water, extract, wash with dilute acid then brine, dry, and concentrate.
For reductive amination: combine the carbonyl compound (1.0 eq) and amine (1.5 eq) in 2‑MeTHF with 0.5 eq AcOH; stir 30–60 min, then add NaBH(OAc)3 (2.0 eq) portionwise; stir at rt 4–16 h; quench with sat. NaHCO3, extract with EtOAc, wash, dry, and purify as needed.
These are generalized procedures intended as starting points. Optimize conditions, stoichiometry, and solvent choices for your specific substrate set and scale. Always conduct appropriate hazard/risk assessments before scaling.
Biological Roles
Item-specific biological data: Not specified for this item; for research use only.
General context (literature):
Aliphatic primary amines are basic nitrogenous compounds that can form ammonium salts at physiological pH. While long-chain aliphatic amines occur in nature (as constituents or precursors to lipids, sphingoid bases, and alkylammonium metabolites), tridecan-7-amine itself is a synthetic structural isomer not known as a major natural metabolite.
Hydrophobic amines readily interact with lipid membranes and can serve as building blocks for cationic surfactants, lipidoids, and delivery materials in research. Protonation state (pH‑dependent) governs membrane association, micelle formation, and ion pairing with anionic lipids or polyelectrolytes.
In biochemical derivatization, primary amines react with activated esters (e.g., NHS esters) and aldehydes (Schiff base formation) enabling conjugation to dyes, linkers, or polymers. The internal positioning at C7 maintains a C6/C6 balance on each side of the amino-bearing carbon, influencing packing and fluidity in assembled materials relative to terminal (ω‑) amines.
Caveat: No biological activity or clinical/therapeutic claims are made for this product. Any biological work should be exploratory and controlled, adhering to institutional biosafety guidelines.
Buffer Applications
Not typically applicable. Tridecan-7-amine is a hydrophobic long-chain primary amine with poor water solubility as the free base and is not used as a conventional buffer component.
Practical notes (general):
If aqueous handling is required, prepare a water-soluble ammonium salt (e.g., HCl, acetate). Such solutions will be acidic due to the counterion and are not true buffers unless paired with the conjugate base in a defined ratio.
For pH adjustments, small, soluble amines (e.g., Tris, ethanolamine) are preferred; this product is better suited as a hydrophobic reagent for synthetic transformations or materials assembly.
Green Alternatives
Perspective: Tridecan-7-amine itself is the target reagent; greenness focuses on solvent/reagent choices and, where relevant, bio-based sourcing of fatty-amine feedstocks.
Greener handling strategies (literature/general):
Solvent selection: prefer 2‑MeTHF or CPME over THF/Et2O; EtOAc or toluene over chlorinated solvents; alcohol/water biphasic systems for salt-forming workups.
Coupling chemistry: use greener coupling agents (e.g., EDC·HCl with catalytic DMAP) and minimize stoichiometric uronium salts. Enzymatic amidation (lipase‑catalyzed) in solvent-free or 2‑MeTHF media is reported for long-chain amines and fatty acids.
Reductive amination: use NaBH(OAc)3 in EtOAc/2‑MeTHF or catalytic hydrogenation (H2, Pd/C or Raney Ni) instead of cyanoborohydrides.
Purification: exploit acid/base extraction and salt crystallization to avoid silica waste from flash chromatography.
Feedstock: where supply allows, consider bio-derived long-chain intermediates (from fatty alcohols/acids) to reduce fossil inputs; life‑cycle benefits are case-dependent.
Comparison snapshot (general):
Chlorinated solvents (DCM/CHCl3): excellent solvation and phase behavior but higher environmental/health impact.
EtOAc/2‑MeTHF/CPME: good solubility for C13 amines, improved safety and sustainability profiles, facile separation.
DMF/DMSO: strong solvation, but EHS concerns and difficult removal; reserve for cases requiring polarity.
Note: The specific product is supplied argon charged, reducing oxidative waste (discoloration/byproducts). Always tailor green choices to reaction requirements and scale.
Pharmaceutical Uses
Item-specific pharmacopeial status/grade: Not specified for this item; refer to CoA/Spec Sheet. For research use only.
General formulation/manufacturing context (no therapeutic claims):
Hydrophobic primary amines serve as intermediates in the synthesis of cationic lipids, surfactants, and excipient-like components (e.g., amide/urea linkers) used in research formulations and materials. The internal amine position at C7 can modulate crystallinity and melting behavior of derived salts relative to ω‑amines.
Salt formation (e.g., hydrochloride, mesylate) can yield crystalline, well-defined solids useful for handling, purification, or as intermediates en route to API side chains. Subsequent neutralization liberates the free base for further derivatization.
In process chemistry, long-chain amines may function as phase-transfer or acid scavengers in non-GMP development work. However, compendial acceptance (USP/Ph. Eur.) and impurity profiles must be established case-by-case; none are provided for this catalog item.
Recommendation: If pursuing regulated applications, establish specification thresholds (residual solvents, nitrosamine risk assessment for amine-containing processes, metals, identity by IR/NMR/MS) and confirm that the supply chain and CoA meet the target quality system before use.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values for 7-aminotridecane (for planning purposes only):
Physical state at ambient conditions: typically a colorless to pale liquid for C13 aliphatic primary amines.
Boiling point (literature, primary C13 amines): approximately 270–285 °C at 1 atm; actual value depends on isomer and purity.
Melting point: long-chain aliphatic amines near C13 often have freezing points below or around room temperature, with possible supercooling; precise MP for tridecan-7-amine not widely tabulated.
Density: typically ~0.80–0.83 g/mL at 25 °C for C12–C14 primary aliphatic amines (literature range).
Refractive index (nD20): often in the 1.44–1.46 range for C12–C14 amines (literature range).
Aqueous solubility: low; aliphatic primary amines are sparingly soluble in water as free bases but become highly soluble as ammonium salts under acidic conditions (literature behavior).
LogP (estimated): high hydrophobicity expected; typical logP for C13 alkyl amines ~4–6 (estimated, method-dependent).
Important: Treat all numerical values above as general/literature guidance. For this specific catalog item, do not treat them as specifications; consult the item’s CoA/Spec Sheet for certified properties.
Quality & Grades
Item-specific grade/purity and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grades (general):
Neat research-grade amines are commonly supplied as free bases with assay typically reported by GC/area% or titration. If a salt form is supplied (e.g., hydrochloride), assay is often reported on anhydrous basis.
HPLC grade (when relevant to solvents) emphasizes low UV background; for reagents like amines, “>98%” or “>99%” assay commonly indicates suitability for synthesis without pre-purification. Low-water grades are favored for moisture‑sensitive couplings.
Stabilizers: Aliphatic amines generally do not require stabilizers, but inert-atmosphere packaging minimizes oxidative discoloration and CO2 uptake. The item-specific note “Argon charged” indicates proactive oxygen/moisture exclusion to preserve color and reactivity.
What to check on the CoA for this item:
Assay method and % purity; residual solvents; water content (Karl Fischer) if reported; color/APHA; GC profile for isomeric purity; acid or amine value; and any metal/halide residues from synthesis.
Identity confirmation: IR (N–H, C–H), 1H/13C NMR, and mass spectrometry; sometimes acid value/amine value is provided for fatty amines.
Recommendation: If high-sensitivity applications (e.g., catalysis, surface functionalization) are planned, verify trace impurity limits on the item’s CoA and perform a brief quality check (e.g., thin-film IR, quick GC) upon receipt.
Reaction & Applications
Chemotype: long-chain, internal primary amine (R–CH(NH2)–R′) with a C13 saturated backbone. The nucleophilic –NH2 enables broad synthetic use.
Representative applications (literature/general):
Amide synthesis: coupling with carboxylic acids (EDC/HOBt, HATU, PyBOP) or with acid chlorides/anhydrides under base (e.g., Et3N, pyridine) to access hydrophobic amides used as surfactant fragments, lipid mimetics, or polymer compatibilizers.
Urea/thiourea formation: reaction with phosgene equivalents (triphosgene, CDI) or isothiocyanates to furnish ureas/thioureas that impart hydrophobicity and H‑bonding capacity in materials or ligands.
Alkylation to secondary/tertiary amines: SN2 with alkyl halides or sulfonates under base (e.g., K2CO3, Cs2CO3) in polar aprotics (DMF/DMSO/MeCN). Reductive amination with carbonyl partners (NaBH3CN, NaBH(OAc)3, or catalytic H2/Raney Ni) provides substituted amines with positional retention at C7.
Quaternization: reaction with alkyl halides to generate quaternary ammonium salts (phase-transfer catalysts, biocidal cationic surfactant precursors). Hydrophobic tail length (C13) tunes CMC and surface activity.
Carbonyl derivatives via oxidation: mild oxidants (e.g., TEMPO/NaOCl not applicable to amines) are unsuitable; however, conversion to amide followed by hydrolysis/oxidation enables functional handle interconversion.
Protective group chemistry: N‑Boc, N‑Cbz, or N‑Fmoc protection to mask basicity during multistep synthesis; deprotect under standard acidic (Boc) or hydrogenolytic (Cbz) conditions.
Practical tips:
Dry, oxygen‑limited conditions minimize discoloration and byproduct imines/amide formation. The item-specific argon charging facilitates this.
Convert to a crystalline salt (e.g., HCl) for easier handling, weighing, or chromatographic purification; regenerate free base with aqueous base and back-extraction into nonpolar solvent.
Reaction Conditions
General conditions from literature for long-chain primary amines (adapt as needed; not item-specific specifications):
Amide couplings:
With carboxylic acids: HATU (1.1–1.5 eq), DIPEA (2.0–3.0 eq), DMF or DCM, 0–25 °C to rt, 1–16 h. EDC·HCl (1.2–1.5 eq) + HOBt or Oxyma works in DCM/DMF/EtOAc; DIPEA or NMM as base.
With acid chlorides/anhydrides: 1.0–1.2 eq acylating agent, 2–3 eq base (Et3N, pyridine) in DCM/toluene, 0 °C to rt, 1–4 h.
Reductive amination:
Carbonyl (1.0 eq), amine (1.2–2.0 eq), AcOH (0.5–1.0 eq) in 2‑MeTHF/EtOAc or MeCN; NaBH(OAc)3 (1.5–2.5 eq) at rt, 2–18 h. Alternatively, H2 (1–5 bar), Pd/C (5–10 wt%), EtOH or toluene, 25–60 °C, 2–8 h.
N‑Alkylation (SN2):
Alkyl halide (1.0–1.5 eq), base (K2CO3 or Cs2CO3, 2–3 eq), MeCN/DMF, 50–80 °C, 4–24 h. Monitor for dialkylation; mitigate by Boc-protecting the amine or using excess amine.
Sulfonamide formation:
TsCl (1.1–1.5 eq), pyridine or Et3N, DCM or MeCN, 0 °C to rt, 2–6 h; catalytic DMAP can accelerate.
Carbamate/urea:
CDI (1.1–2.0 eq) in THF/2‑MeTHF, rt to 50 °C, 2–16 h; or triphosgene (0.33 eq) under controlled addition with base.
Salt formation/crystallization:
Dissolve amine in EtOAc/MTBE, bubble dry HCl or add HCl in dioxane to precipitate ammonium chloride salt; 0–5 °C to improve crystallinity.
Typical workup considerations:
Partition between organic solvent and dilute acid/base to toggle between free base and ammonium salt for efficient purification.
Dry organic phases thoroughly (MgSO4/Na2SO4); concentrate under reduced pressure below 40–50 °C to mitigate loss or discoloration.
Yields: Commonly high (70–95%) for clean acylations and reductive aminations with long-chain amines, contingent on reagent quality and stoichiometry.
Safety & Handling
Item-specific hazard classification: Not specified for this item; refer to SDS.
General safety profile for aliphatic primary amines (literature/typical):
GHS considerations: many long-chain primary amines are classified as skin and eye irritants; some may be corrosive and hazardous to aquatic life. Always consult the item-specific SDS for authoritative classification, pictograms, and H/P statements.
Volatility/odor: amines have characteristic strong odors; minimize inhalation exposure by working in a fume hood.
Incompatibilities: strong oxidizing agents, acid chlorides/anhydrides, isocyanates (vigorous reactions); strong acids will form ammonium salts (exothermic, heat release). Avoid copper and other metals that can catalyze discoloration/oxidation.
Peroxide formation: not a peroxide-forming class; however, amines can oxidize in air/light to form imines, nitroso derivatives, or amides—store under inert gas as specified for this item.
Personal protective equipment (typical): lab coat, nitrile gloves, splash goggles; consider face shield for bulk handling. Use in a chemical fume hood.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: combustible organic liquid; use CO2, dry chemical, or foam. Amines may produce toxic nitrogen oxides upon combustion.
Always follow institutional protocols and the item-specific SDS.
Solvent Selection
Applicability: Tridecan-7-amine is a hydrophobic, long-chain aliphatic primary amine; it is not used as a solvent. This section focuses on choosing solvents to dissolve and manipulate it as a reagent.
Limited solubility in alcohols and acetonitrile may occur at room temperature; solubility increases with mild heating.
Sparingly soluble in water as the free base; fully water-soluble upon protonation (e.g., as the hydrochloride salt).
Selection guidance:
For nucleophilic substitutions, reductive amination, and base-mediated acylations, use anhydrous ethers (THF, CPME) or aprotics (toluene, xylene) to limit competing protonation.
For amide couplings using carbodiimide or uronium reagents, DMF, DCM, or EtOAc are common; if avoiding dipolar aprotics, CPME/2-MeTHF with catalytic base often work.
For salt formation/purification, dissolve the amine in a water-immiscible organic phase (EtOAc, DCM), then extract into dilute HCl; back-neutralize as needed.
Brief comparison (general):
2-MeTHF/CPME vs THF/Et2O: greener, higher boiling, and better phase separation; similar solubility for C13 amines.
Toluene vs hexanes: toluene dissolves the amine more effectively and tolerates higher temperatures for acylations or hydrogenations.
Storage & Reconstitution
Item-specific storage and shipping:
Storage Conditions: Protected from light; Room temperature; Argon charged (as provided). Keep container tightly closed to maintain inert atmosphere and limit CO2 uptake/oxidation.
Shipped In: Normal.
General handling guidance (for aliphatic amines):
Store in amber or foil-protected containers with PTFE-lined caps. If repeated access is expected, consider using inert gas blankets (argon or nitrogen) after each use.
Moisture/air sensitivity: While not highly air-sensitive, long-chain amines can discolor on exposure to air/light and absorb CO2 to form ammonium carbamates; the provided argon charging helps mitigate this.
If material partially solidifies in a cold room or during winter shipping, warm gently to ambient (or to ~30–35 °C in a water bath) and mix thoroughly before use.
Reconstitution: Supplied neat. No reconstitution required. For solution preparation, common anhydrous solvents include toluene, 2‑MeTHF, CPME, THF, EtOAc, DCM, or hexanes. Prepare stock solutions under inert gas if prolonged storage is planned.
Freeze–thaw: Not typically applicable. Avoid repeated heating/cooling cycles that may induce oxidation; aliquot if needed for long-term studies.
Always refer to the product’s CoA and SDS for definitive storage stability, shelf life, and compatibility information. Research use only.
Structure & Identity
Item-specific identifiers (from Product Data):
SKU: T405050
Product Name: Tridecan-7-amine
CAS: 22513-16-2
PubChem CID: 574991
InChIKey: 94806 (as provided)
Storage note (item-specific): Protected from light; Room temperature; Argon charged.
Literature/computed structural information (general, not item-specific):
Molecular formula (for 7-aminotridecane): C13H29N (literature/computed)
SMILES (one possible representation): CCCCCC(N)CCCCCC (literature/computed)
Functional group(s): primary aliphatic amine attached to an internal (secondary) carbon within a C13 linear alkyl chain.
Structural description (2D): a straight, saturated 13‑carbon chain with an –NH2 substituent at C7 (the chain center), rendering the carbon bearing the amino group secondary; no rings, no unsaturation, no heteroatoms other than nitrogen; achiral in its free base form.
Notes:
Where conflicts exist, rely on the Certificate of Analysis (CoA) and Specification Sheet for definitive identity parameters and exact notations for this catalog item.
Synthetic Utility
Functional handles and logic:
Primary amine (internal): strong nucleophile/base; enables acylation, alkylation, sulfonylation, carbamate/urea formation. Internal placement provides a C6–NH2–C6 motif influencing derived molecule symmetry and material properties.
Amide formation: with acids (EDC/HOBt, HATU) or acid chlorides (Et3N, pyridine) in DCM/DMF/EtOAc/2‑MeTHF.
Reductive amination: condensation with ketones/aldehydes followed by NaBH(OAc)3 or catalytic H2 (Pd/C, Raney Ni) to give secondary amines; subsequent iteration affords tertiary amines.
N‑Alkylation: SN2 with alkyl halides/tosylates (K2CO3/Cs2CO3, DMF/MeCN). Control over over‑alkylation via protecting groups (Boc) or stoichiometry.
Sulfonamide formation: with sulfonyl chlorides (e.g., TsCl, MsCl) in pyridine or with base; useful for directing groups or as stable protecting derivatives.
Carbamate/urea: CDI or triphosgene to make symmetrical/unsymmetrical ureas; chloroformates to make carbamates (removable under acid/base or hydrogenolysis depending on group).
Surface immobilization: coupling to activated carboxyl surfaces (e.g., EDC/NHS-activated polymers, nanoparticles) to present a hydrophobic tail with a central junction.
Protecting group strategy:
Boc protection simplifies selective N‑functionalization; removal with TFA/DCM or HCl/dioxane. Cbz offers hydrogenolytic deprotection when acid-labile groups are present.
Purification tips:
Form acid salts (HCl, p‑TSA) to induce crystallinity and enable trituration; regenerate free base with NaHCO3/Na2CO3 and extract into nonpolar solvents.
Target Specificity
Not applicable. This product is a small-molecule aliphatic amine, not an antibody, enzyme, or affinity reagent. No antigen/epitope or species reactivity claims apply. Refer to the Reaction & Applications and Synthetic Utility sections for relevant use cases.
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