6-(Methylamino)hexan-1-ol - ≥95% , CAS No.50347-17-6

CAS: 50347-17-6 Cat. No.: M1067868 Formula: C₇H₁₇NO Molecular Weight: 131.22 EC Number: 890-456-4 PubChem CID: 10942457

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CNCCCCCCO
• IUPAC Name: 6-(methylamino)hexan-1-ol
• InChIKey: RURWAYHDLRPVAE-UHFFFAOYSA-N
• INCHI: 1S/C7H17NO/c1-8-6-4-2-3-5-7-9/h8-9H,2-7H2,1H3
• Isomeric SMILES: CNCCCCCCO
• PubChem CID: 10942457
• Molecular Weight: 131.22

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Not available
• Direct Parent: Alkanolamines
• Alternative Parents: Dialkylamines Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Secondary amine - Secondary aliphatic amine - Alkanolamine - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as alkanolamines. These are organic compounds that carry a hydroxy and an amino functional groups on an alkane backbone.
• 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

Chemical and Physical Properties

• Molecular Weight: 131.220 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 131.131 Da
• Monoisotopic Mass: 131.131 Da
• Topological Polar Surface Area: 32.299 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 48.200
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• 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

Not applicable as a tested bioassay reagent. No vendor-validated protocols (e.g., WB, IHC, IF, FC) or dilutions are associated with this small-molecule building block.

General usage notes (context)

• For coupling to activated esters (e.g., NHS esters): dissolve 6-(methylamino)hexan-1-ol in aqueous buffer (pH 8.5, 50–100 mM bicarbonate or borate) with co-solvent (10–30% DMF) to 10–50 mM; add 1.1–1.5 eq activated ester; react 1–2 h at rt. Purify by chromatography or preparative HPLC. Adjust conditions to your system.
• For O‑activation (tosylation): dry DCM, 0 °C; add TsCl (1.2 eq) and Et3N (2 eq) with catalytic DMAP; warm to rt and stir 2–6 h; quench with aqueous NaHCO3; extract and purify. Protect the amine if selectivity issues arise.

These are illustrative, literature-style procedures and are not item-specific validated protocols.

Biological Roles

This catalog item is provided for research use only. No clinical or in vivo claims are made.

General biochemical context for aliphatic amino alcohols (literature; not product-specific)

• Motif prevalence: amino alcohol units occur widely in biomolecules (e.g., sphingolipids, certain natural products) where juxtaposed hydrogen-bond donor/acceptor groups modulate binding and solubility.
• Ionization behavior: secondary amines are protonated near neutral pH (conjugate acid pKa typically ~10–11), enhancing aqueous solubility; the alcohol group remains largely unionized, contributing to amphiphilicity.
• Interactions: amino alcohols can engage in salt-bridge and H‑bond networks with proteins and nucleic acids; in membranes, longer alkyl chains increase hydrophobic partitioning while the polar headgroup maintains interfacial anchoring.
• Chemical biology utility: ω-amino-ω′-hydroxy chains serve as spacers/linkers for probe construction, surface immobilization, and bioconjugation (e.g., forming amide/carbamate linkages to biomolecules or resins).

Practical notes

• For bioconjugation, control protonation state (adjust pH to 8–9) to favor nucleophilicity of the amine during coupling (e.g., NHS ester chemistry). Protect the alcohol if selective N‑modification is required.
• Salt forms: protonated salts (e.g., HCl) can facilitate handling and reduce volatility; freebase is typically required for nucleophilic substitution or reductive amination steps.

Buffer Applications

Not a dedicated buffering agent. Secondary aliphatic amines exhibit conjugate-acid pKa typically in the ~10–11 range (literature), which is outside common physiological buffering windows.

Guidance (general)

• While the protonated amine can contribute to alkalinity near pH ≥9, amino alcohols like 6-(methylamino)hexan-1-ol are not used as primary buffers due to limited buffering capacity and interference in biochemical assays.
• If present in assay media (e.g., as a linker or additive), maintain ionic strength and buffering with standard systems (e.g., Tris, HEPES, PBS). Adjust pH to keep the amine in the desired ionization state for reactivity while relying on an established buffer for pH control.

Recommendation

• Use established buffers (Tris pKa 8.1, HEPES pKa 7.5, MOPS pKa 7.2; literature) for pH maintenance. Employ this compound only as a reactant or spacer, not as a buffer component.

Green Alternatives

Context: This product is a functionalized building block rather than a commodity solvent. “Greener” considerations therefore focus on solvent choice, protecting-group economy, and safer reagents in transformations involving 6-(methylamino)hexan-1-ol.

Opportunities for greener practice (general guidance)

• Solvent selection: prioritize low-toxicity, bio-derived, or high‑boiling recyclable solvents (e.g., 2-MeTHF, CPME, propylene carbonate) when compatible, instead of chlorinated solvents. Water/ethanol mixtures often support imine chemistry and acylations with suitable coupling reagents.
• Coupling chemistry: EDC·HCl with catalytic DMAP in aqueous/ethanol media can replace carbodiimides that generate problematic ureas; avoid HOBt/HOAt for safety. Enzymatic esterifications (lipases) in green solvents may form O-derivatives under mild conditions.
• Protection-minimization: exploit intrinsic chemoselectivity (e.g., faster N‑acylation) to avoid sequential protection/deprotection steps, reducing reagent and solvent use.
• Energy efficiency: many transformations proceed at ambient temperature with appropriate catalysts (e.g., DMAP for acyl transfer; phase-transfer catalysis for substitutions), cutting heating/cooling demands.

Illustrative comparison (general)

• Chlorinated solvent (DCM) for acylation: excellent selectivity but hazardous and waste-intensive.
• Alternative: 2-MeTHF or ethyl acetate with catalytic DMAP and base can deliver comparable conversions for N‑acylation while improving environmental profile (literature reports).

Trade-offs

• Highly polar substrates like amino alcohols may require polar aprotics (DMF/DMSO). Where used, implement solvent recovery and minimize volumes to mitigate EHS impacts.

Pharmaceutical Uses

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

General formulation/manufacturing context (literature; not product-specific)

• Amino alcohols are common motifs in drug-like molecules and can serve as intermediates to amides, carbamates, and quaternary ammonium salts. 6-(Methylamino)hexan-1-ol can function as a synthetic intermediate to generate cationic or amphiphilic entities.
• Salt formation: secondary amines readily form stable mineral acid salts (e.g., HCl), which can improve crystallinity and handling during process development.
• Impurity control: due to high polarity and hydrogen-bonding, residual amino alcohols can be challenging to purge; process crystallization or ion-exchange can aid removal.
• Derivatization strategies: converting the alcohol to carbonate/ester or the amine to an amide can tune lipophilicity and solid-state properties for downstream intermediates.

Compliance note

• Any use in human or veterinary products requires appropriate regulatory assessment and qualification. This listing provides no claims regarding GMP status, residual solvent limits, or compendial alignment. Consult your QA/QC and regulatory teams accordingly.

Physical Properties

Item-specific specs

• Not specified for this item; refer to CoA/Spec Sheet for any definitive physical constants (bp, mp, density, refractive index, water content, UV cutoff, metal limits, etc.).

General/literature characteristics of 6-(methylamino)hexan-1-ol (for context only)

• Physical state: typically a low-melting, viscous liquid or low-melting solid depending on purity and salt form (freebase is generally a hygroscopic liquid) (literature)
• Polarity: bifunctional, strongly hydrogen-bonding; both H-bond donor and acceptor (alcohol and secondary amine)
• Solubility: expected to be miscible or highly soluble in polar protic solvents (water, methanol, ethanol) and many polar aprotic solvents (DMF, DMSO); limited solubility in nonpolar hydrocarbons (literature, qualitative)
• Basicity: secondary aliphatic amine with conjugate acid pKa typically ~10–11; hydroxyl pKa ~16 (alcohol) (literature, typical ranges for secondary amines/aliphatic alcohols)
• Volatility: low relative volatility vs C6 alcohols due to strong intermolecular H-bonding; tends to have high bp and low vapor pressure (literature, qualitative)
• Hygroscopicity: amino alcohols often show moisture uptake and may form viscous films (literature, qualitative)

Practical implications

• Highly polar; can complicate GC without derivatization (silylation/acylation). LC methods generally preferred.
• Strong adsorption on silica may occur; add base modifier (e.g., 0.1% Et3N) for normal-phase chromatography (general guidance).

Always verify measurable properties for this specific lot on the CoA.

Quality & Grades

Item-specific quality information

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

Guidance on typical grades for small-molecule reagents (general)

• Research grade: suitable for most synthetic/biochemical workflows; may include low-level volatile/non-volatile impurities.
• High-purity or >98% grade: facilitates analytical use and reactions sensitive to amine/alcohol impurities; reduces background in derivatizations and polymerizations.
• Salt vs freebase: Amino alcohols may be offered as freebase or as salts (e.g., HCl). Salt forms can enhance handling (solid, reduced volatility) and stability but require basification for freebase chemistry. The form for this item is not specified.
• Stabilizers: None stated for this item. If a stabilizer were present, it could impact catalytic or analytical applications; always check CoA.

Quality control considerations (general)

• Identity confirmation: 1H/13C NMR (bifunctional pattern), IR (broad OH/NH bands), HRMS.
• Purity profiling: GC or LC with base-modified mobile phase; derivatization (e.g., acylation/silylation) can improve chromatographic behavior.
• Residual solvents, water content, and titratable amine: important for stoichiometric reactions; Not specified for this item—consult CoA.

Reaction & Applications

Chemotype: bifunctional aliphatic amino alcohol (secondary amine + primary alcohol). This makes it a versatile building block and linker.

Representative applications (literature/general)

• Linker for conjugation: the ω-amino and ω-hydroxyl termini enable orthogonal derivatization to install one group at nitrogen (e.g., acyl, Boc, sulfonyl) and another at oxygen (e.g., ester, carbonate), generating amphiphiles or surface modifiers.
• Amide synthesis: selective acylation of the amine with acid chlorides/anhydrides or coupling agents (EDC/HOBt, HATU) to give N-acyl derivatives; subsequent O-functionalization expands diversity.
• Carbamate/urethane formation: reaction with chloroformates (e.g., Boc2O or p-nitrophenyl chloroformate) to form N- or O‑carbamates; useful for protecting-group strategies or polymer precursors.
• Tosylation/mesylation of the alcohol: formation of OTs/OMs provides a leaving group for intramolecular cyclizations (e.g., morpholinium-type derivatives after N-alkylation) or for SN2 substitution to introduce heteroatoms.
• Reductive amination: the secondary amine can be further alkylated via imine formation with aldehydes/ketones followed by reduction (NaBH3CN, BH3·THF), enabling tailored tertiary amines.
• Quaternization: alkyl halides can quaternize the amine to yield ammonium salts with surfactant-like properties (longer chains enhance CMC effects).
• Metal chelation/ligands: amino alcohols coordinate metals; derivatized motifs serve as chiral/achiral ligands in catalysis (this substrate is achiral unless further modified).

Practical tips

• Chemoselectivity: amine acylation is faster than alcohol acylation under many conditions; use base and low temperature to favor N-acylation. For O-selectivity, protect the amine or employ catalysts (DMAP) with hindered/activated acyl donors.
• Dry conditions: for acylations and carbamoylations, rigorously dry solvents and use molecular sieves to suppress side hydrolysis.

Reaction Conditions

General literature conditions for typical transformations of aliphatic amino alcohols (guidance only; optimize per substrate):

• N‑Acylation (selective):

  • Reagents: acid chloride or anhydride; base (DIPEA, Et3N)
  • Solvent: DCM, THF, or MeCN (anhydrous)
  • Temperature/time: 0–25 °C, 0.5–4 h
  • Notes: amine acylation generally outpaces alcohol acylation; add acylating agent slowly at 0 °C to maximize N‑selectivity.

• O‑Tosylation (alcohol activation):

  • Reagents: TsCl (1.1–1.5 eq), base (pyridine or Et3N), catalytic DMAP
  • Solvent: DCM or MeCN
  • Temperature/time: 0 °C → rt, 2–12 h
  • Notes: protect amine (e.g., Boc) if N‑tosylation competes.

• Reductive amination to tertiary amine:

  • Reagents: aldehyde (1.0–1.2 eq), NaBH3CN or NaBH(OAc)3
  • Solvent: MeOH, EtOH, or DCE/AcOH; pH ~6–7 (acetic acid buffer)
  • Temperature/time: rt, 2–16 h
  • Notes: monitor by LC; quench carefully; avoid strong acid to prevent cyanide liberation with NaBH3CN.

• Carbamate (urethane) formation at N:

  • Reagents: Boc2O (1.1 eq) or chloroformate; base (NaHCO3 or DIPEA)
  • Solvent: DCM, THF, or water/THF biphasic
  • Temperature/time: 0–25 °C, 1–3 h

• Mesylation/halogenation of alcohol:

  • MsCl/Et3N in DCM, 0–25 °C; or PBr3 (alcohol → bromide) in ether at 0–5 °C (caution with amine—protect if needed).

Purification tips

• Strong silica interactions; add 0.1–1% Et3N to eluent. Alternatively, convert to HCl salt for trituration/crystallization, then basify to regenerate freebase.

Safety & Handling

GHS information for this catalog item

• Signal word, H-statements, pictograms, and classification: Not specified for this item; refer to SDS for authoritative information.

General safety profile for aliphatic secondary amine alcohols (context only; not product-specific)

• Hazards: can be irritating to skin, eyes, and respiratory tract; secondary amines may form nitrosamines upon contact with nitrosating agents under acidic conditions; amino alcohols can be corrosive at high concentrations.
• Incompatibilities: strong oxidizers; acylating/alkylating agents (uncontrolled reaction); nitrites/nitrosating agents; acid chlorides/anhydrides (vigorous acylation); CO2 can form carbamates with amines on prolonged air exposure.
• PPE: chemical-resistant gloves (e.g., nitrile), lab coat, safety glasses/goggles; use in fume hood to minimize vapor/aerosol exposure.
• First aid (overview; follow SDS):
  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin contact: wash with soap/water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: amino alcohols are combustible organics; use CO2, dry chemical, or foam; water spray for cooling containers.
• Spill response: absorb with inert material; avoid contact with acids/nitrosating agents; ventilate area.

Always consult the product SDS for definitive hazard classification, exposure limits, and emergency procedures.

Solvent Selection

Applicability

• This product is a bifunctional reagent, not primarily a solvent. However, appropriate reaction/handling solvents are crucial due to its polarity and hydrogen-bonding.

Solubility/miscibility profile (general, literature)

• Highly soluble in water, alcohols (MeOH, EtOH, i-PrOH), and polar aprotic media (DMF, DMSO, NMP, acetonitrile). Limited solubility in nonpolar hydrocarbons (hexanes, toluene) unless protonated/salt forms are avoided.

Selection guidance

• Nucleophilic reactions or acylations: use dry polar aprotics (DCM, MeCN, THF, DMF) with base to control protonation of the amine.
• Reductive amination or N-alkylation: MeOH/EtOH or MeCN commonly used; water co-solvent can help for imine formation with subsequent reduction (NaBH3CN, borohydrides).
• Protection chemistry (Boc, Cbz): DCM, THF, or MeCN with base (e.g., DIPEA). Keep water low to avoid carbonate hydrolysis.
• O-functionalization (tosylation/mesylation): DCM, MeCN, or pyridine; maintain low temperature for selectivity.

Comparison (general)

• Versus shorter amino alcohols (e.g., 3-aminopropanol): longer chain lowers basicity slightly via inductive effects and improves hydrophobic interactions in extractions.
• Versus diamines: amino alcohols are less basic and more hydrophilic, often simplifying workups.

Always validate solvent choice experimentally for your substrate set.

Storage & Reconstitution

Item-specific guidance

• Storage Conditions: Room temperature (as provided in Product Data).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Form and reconstitution: Not specified for this item; refer to CoA/Spec Sheet.

General best practices for amino alcohols (context)

• Keep container tightly closed under inert headspace if possible to minimize CO2 uptake (carbamate formation) and moisture ingress.
• If offered as a freebase liquid: store in amber glass to limit light exposure; use dry septa if frequent access is required; consider refrigeration (2–8 °C) for long-term stability if compatible with item guidance.
• If offered as a crystalline salt (e.g., HCl): store desiccated to avoid caking; freebase can be regenerated by basification and extraction.
• Stability: avoid prolonged contact with strong oxidizers and nitrosating conditions. For sensitive transformations, freshly distill or pass through a short plug of basic alumina to remove adventitious acids.

Before use

• Allow to reach ambient temperature; if solidified or viscous, gently warm and vortex/sonicate to homogenize. Verify concentration by weight or titration if using as a stoichiometric base/nucleophile.

For precise storage limits, retest periods, and container materials, consult the product’s CoA and SDS.

Structure & Identity

Brief description: 6-(Methylamino)hexan-1-ol is a bifunctional aliphatic amino alcohol bearing a terminal primary alcohol and a secondary amine (N-methyl) at the ω-position.

• Item-specific identifiers (from Product Data)
  • SKU: M1067868
  • Product Name: 6-(Methylamino)hexan-1-ol
  • CAS: 50347-17-6
  • PubChem CID: 10942457
  • InChIKey: 326532 (as provided; note this is not a standard-length InChIKey)
  • Storage: Room temperature
• Not specified for this item; refer to CoA/Spec Sheet
  • Grade/Purity, Appearance, SMILES, Molecular Formula, Molecular Weight
• Literature/computed identifiers and structural description (for general reference; not item-specific specifications)
  • Typical molecular formula (literature): C7H17NO
  • Typical molecular weight (literature): ~131.22 g/mol
  • Example SMILES (literature): CNCCCCCCO (depicts HO–(CH2)6–NH–CH3)
  • Functional groups: one terminal primary alcohol (–CH2OH) and one secondary amine (–NH–CH3) separated by a six‑carbon polymethylene spacer
  • Structural features (2D description): a linear C6 chain with –OH at C1 and –NH–CH3 at C6; no rings, no stereocenters, fully saturated aliphatic backbone

Notes

• Literature data are provided for context only and may not represent the exact specification of this catalog item. Consult the CoA/SDS for definitive identity and quality attributes.

Synthetic Utility

Functional group handles and reactivity

• Secondary amine (N–Me): nucleophilic; amenable to acylation, sulfonylation, alkylation (to tertiary amines), and quaternization. Forms imines/enamines under dehydrating conditions with carbonyls (more commonly for primary amines; secondary amines favor iminium formation for reductive amination).
• Primary alcohol: oxidizable (to aldehyde/acid), activatable to sulfonates (OTs/OMs), carbonates, or halides for SN2; can undergo esterification and carbonate/urethane formation.

Strategic uses (literature)

• Orthogonal protection: protect N (Boc, Cbz) to selectively derivatize O (e.g., tosylate for chain extension or intramolecular cyclization). Alternatively, protect O (TBDMS) to functionalize N.
• Spacer/linker chemistry: the C6 spacer provides conformational flexibility and distance between functional nodes—useful in attaching polar heads to hydrophobic tails to generate amphiphiles or in resin/solid-support tethering.
• Cyclizations: after O‑activation to OTs and intramolecular SN2 onto a tertiary amine precursor, one can access morpholine-like or ammonium macrocycles (chain length governs ring size/yield).
• Reductive amination: convert to tertiary amines by condensing with aldehydes (R–CHO) followed by reduction (NaBH3CN or NaBH(OAc)3 in MeOH/AcOH).
• N‑Oxidation and subsequent rearrangements: tertiary derivatives may be oxidized (mCPBA) and engaged in Polonovski-type chemistry (where applicable).

Handling for synthesis

• Keep moisture low for coupling/activation steps; add base (DIPEA, triethylamine) to maintain amine nucleophilicity. For chromatographic purification, add basic modifiers to prevent streaking on silica.

Target Specificity

Not applicable. This product is a small-molecule amino alcohol, not an antibody, enzyme, or targeted biological reagent.

• No antigen/epitope, clone, isotype, or species reactivity data apply.
• For biochemical conjugations, “specificity” arises from chosen coupling chemistries (e.g., NHS ester to lysine residues), not from intrinsic molecular recognition by this compound.