1-Heptanol-d , CAS No.1219804-99-5

CAS: 1219804-99-5 Cat. No.: H1451093 Formula: C₇H₉D₇O Peso molecolare: 123.24

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

1-Heptanol-d 7 is the deuterium labeled 1-Heptanol.

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

123.24

Application Protocols

No antibody/assay kit protocols apply to this small‑molecule reagent.

General research usage notes:

• NMR: Use as a deuterated additive/solvent to suppress the hydroxyl 1H resonance and/or to probe exchange via 2H NMR. Dry thoroughly to maintain OD enrichment; acquire spectra promptly after sample prep if exposed to moisture.
• IR/Raman: Track O–D stretching band to study hydrogen‑bonding; prepare samples in dry cells to avoid back‑exchange.
• Partitioning/membrane studies: Prepare stock solutions in suitable organic solvents; titrate into aqueous or bilayer systems at controlled temperatures, monitoring turbidity and phase behavior.

For detailed, application‑specific procedures, consult primary literature and adjust conditions to your experimental system. This product is provided for research use only.

Biological Roles

General biochemistry perspective (literature; not item-specific):

• Medium‑chain alcohols like 1‑heptanol are amphiphiles that partition into lipid bilayers, altering membrane fluidity and phase behavior. This can modulate protein function indirectly by changing bilayer physical properties.
• 1‑Heptanol is reported in electrophysiology as a reversible gap‑junction uncoupler, attributed to its effects on connexin‑mediated intercellular communication through membrane perturbation. These effects are widely used as tools in basic research but are not therapeutic claims.
• In enzyme systems, higher alcohols can act as competitive substrates or inhibitors for alcohol dehydrogenases to varying degrees, though activity declines with chain length due to solubility and steric factors.
• Isotopic note: Substitution of the hydroxyl hydrogen by deuterium minimally affects partitioning but enables spectroscopic discrimination (e.g., IR O–D band) and reduces 1H background in NMR of complex biological mixtures.
• Toxicology context: Cytotoxicity tends to increase with chain length among alkanols; 1‑heptanol exhibits stronger membrane‑perturbing effects than short‑chain alcohols, which should be considered when designing in vitro assays.

All uses are for research purposes only. For cellular or biochemical experiments, verify solvent controls and maintain final concentrations below levels known to compromise membrane integrity or enzyme function.

Buffer Applications

This product is a hydrophobic primary alcohol, not a buffering agent. It does not form defined conjugate acid/base pairs suitable for maintaining pH in aqueous systems.

Practical notes for aqueous work:

• Limited water solubility (~3–4 g/L, literature) means it is typically used as a co‑solvent or additive rather than a buffer component.
• If OD enrichment is important, avoid aqueous buffers altogether because the O–D will exchange rapidly with water, eliminating isotopic labeling at the hydroxyl.

For pH control, use established buffer systems (e.g., phosphate, HEPES, Tris), and introduce 1‑heptanol‑d as a separate co‑solvent phase or in minimal volumes as required by the experimental design.

Green Alternatives

Perspective: 1‑Heptanol (and its OD isotopologue) is a medium‑boiling, combustible, VOC‑class solvent with moderate toxicity. As a primary alcohol from petro‑ or bio‑based fatty alcohol streams, it can sometimes be sourced renewably. Greener choices depend on the task.

Comparison (literature-based, general):

• 1‑Heptanol vs 2‑MeTHF/CPME
  • Advantages of 1‑heptanol: Protic H‑bond donor; good for esterifications, phase‑transfer scenarios, and membrane‑mimetic studies; higher boiling point for elevated‑temperature reactions.
  • Tradeoffs: Lower biodegradability data availability compared to bio‑solvents; slower drying; partial water miscibility can complicate workups.
• 1‑Heptanol vs ethanol/i‑PrOH
  • Advantages: Lower volatility and higher hydrophobicity, enabling unique solvation of lipophiles and reduced flammability risk at room temperature.
  • Tradeoffs: Higher toxicity than ethanol; poorer green‑score in many solvent guides; slower mass transfer.

Green practice recommendations:

• Source bio‑based grade when available (fatty alcohol route) to lower carbon intensity.
• Recycle via fractional distillation; the high boiling point facilitates recovery.
• Minimize air emissions; use closed transfers and cold traps when heated.
• For OD‑labeled material: because isotopic synthesis has a higher footprint, plan experiments to minimize waste and recover/repurpose material where feasible.

If a greener protic solvent suffices analytically, consider deuterated ethanol‑d (if properties allow) or deuterated 2‑propanol‑d, recognizing their higher volatility and different hydrogen‑bonding profiles.

Pharmaceutical Uses

No pharmacopoeial grade or excipient designation is provided for this item. Deuterated 1‑heptanol (OD) is not typically used as a formulated excipient.

General formulation/processing context (literature):

• Medium‑chain alcohols are sometimes explored as penetration enhancers in topical formulations and as co‑solvents for poorly soluble actives. However, routine pharmaceutical excipient use is far more common with shorter alcohols (ethanol, isopropanol) or specific fatty alcohols (cetyl/stearyl) with established compendial monographs.
• For process chemistry, 1‑heptanol may serve as a reaction solvent, an esterification alcohol to produce heptyl esters (as intermediates), or as a phase modifier in extractions.
• Isotopic (deuterated) variants are generally reserved for analytical development (e.g., mechanistic studies, tracer work), not for production formulations.

If excipient use is contemplated in research settings, confirm toxicological acceptability, residual limits, and extractables/leachables compatibility. For regulated applications, only use compendial grades with appropriate documentation; this product is provided for research use only.

Physical Properties

Item-specific specifications (this lot):

• Boiling point, melting point, density, refractive index, water content, isotopic enrichment: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general values (protiated 1‑heptanol unless noted; deuteration at OH minimally perturbs bulk properties):

• Typical boiling point: ~176–177 °C at 1 atm (literature).
• Melting point: approximately −34 °C (literature).
• Density: ~0.82 g/mL at 20 °C (literature, neat 1‑heptanol).
• Refractive index (nD20): ~1.429–1.430 (literature).
• Vapor pressure: low; ~0.2–0.3 mmHg at 25 °C (literature, order of magnitude).
• Water solubility: low; ~3–4 g/L at 20–25 °C (literature), forming biphasic mixtures above solubility limit.
• Partition coefficient (logP): ~2.6–2.7 (literature, 1‑heptanol), consistent with amphiphilic/medium hydrophobicity.
• pKa (of conjugate acid ROH2+): ~−2 (literature); neutral alcohol is very weak acid (pKa ~16–17 in DMSO, literature). O–D exchangeable with H2O/acid/base.
• Dielectric constant (ε, 20–25 °C): ~12–13 (literature), intermediate-polarity protic solvent.

Notes for deuterated material:

• The O–D stretching frequency shifts down relative to O–H (IR), aiding spectral deconvolution.
• Isotopic substitution may change MW by +1 and slightly shift NMR lines (e.g., suppress 1H signal at the hydroxyl). Physical constants are otherwise very similar to the protiated analogue.

Quality and Grades

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

Context for deuterated small molecules:

• Isotopic enrichment: For research that depends on low proton background (e.g., NMR lock/SHIM considerations, neutron scattering contrast), the deuterium incorporation at the hydroxyl should be verified. The CoA typically reports %D at the OH position. Because –OD is exchangeable, enrichment can diminish with exposure to moisture, acids, or protic solvents.
• Typical quality metrics reported (check this item’s CoA):
  • Isotopic enrichment at the hydroxyl (%D).
  • Residual protiated alcohol content (1‑heptanol).
  • Residual solvents or stabilizers (if any) and water content (Karl Fischer).
  • GC purity area % and identity confirmation (1H/13C NMR; sometimes 2H NMR, FT‑IR O–D band).

Grade implications (general):

• “Isotopic” or “deuterated” research grade generally prioritizes isotopic labeling and chemical purity; UV cutoff and trace metals are typically not key specifications unless for spectroscopic or catalytic studies.
• If HPLC‑grade or LC‑MS‑grade is offered (not specified here), that would signify very low nonvolatile residue and low background suitable for trace analysis.

Recommendations:

• On receipt, verify isotopic enrichment by quick 1H NMR (suppressed/absent OH signal) or by 2H NMR/IR (O–D stretch). If enrichment is critical, minimize contact with water and store tightly sealed at −20 °C as directed.

Reaction and Applications

Research uses specific to 1‑Heptanol‑d (isotopic):

• Spectroscopy and mechanistic probes:
  • O–D stretch (IR) provides a clean, shifted band relative to O–H, enabling hydrogen‑bonding strength studies and kinetic isotope effect (KIE) evaluation at the hydroxyl.
  • 2H NMR tracer for monitoring exchange at the hydroxyl and for reducing 1H background from labile protons in complex spectra.
• Partitioning/membrane studies: The C7 chain length sits between widely used 1‑hexanol and 1‑octanol; the OD label facilitates neutron‑scattering contrast variation and reduces 1H incoherent background.

General synthetic/reactive applications (apply equally to protiated analogue):

• Nucleophilic substitution after activation:
  • Convert to 1‑heptyl sulfonates (e.g., tosylate/mesylate) for SN2 with halides, azide, thiolates (heptyl derivatives).
  • Halogenation (PBr3, SOCl2) to 1‑bromoheptane/1‑chloroheptane as versatile alkylation agents.
• Oxidation: PCC, TEMPO/bleach, or Swern to heptanal; further oxidation (Jones/Pinnick or TEMPO/oxone) to heptanoic acid.
• Esterification/transesterification: Fisher esterification or DCC/EDC coupling to make heptyl esters (useful as hydrophobic tails, fragrance/monomer precursors).
• Dehydration: Acid‑catalyzed to internal heptenes; subsequent hydrofunctionalization (e.g., epoxidation, hydroboration).

Isotope-specific caution:

• The –OD deuteron is exchangeable and will be lost under most acidic/basic or aqueous conditions. For permanent deuterium incorporation in the carbon skeleton, use C‑deuterated analogues instead of –OD‑only labeling.

Reaction Conditions

General conditions (literature guidance for 1‑heptanol transformations; adjust for scale and substrate sensitivity):

• Tosylation/mesylation (to activate as leaving group):
  • Reagents: TsCl (1.1–1.5 eq) or MsCl (1.1–1.5 eq), base (pyridine, Et3N, or DMAP catalytic), 0–25 °C, 1–3 h (TsCl) or shorter for MsCl. Typical isolated yields: 80–95%.
• Halogenation to 1‑bromoheptane/1‑chloroheptane:
  • PBr3 (0.33–0.5 eq) in dry ether/THF, 0 °C → rt, 1–2 h; or SOCl2 with catalytic DMF in DCM, 0 °C → reflux. Typical yields: 70–90%.
• Oxidation to heptanal:
  • Swern (oxalyl chloride/DMSO, −78 °C → 0 °C; Et3N quench) or Dess–Martin in DCM at rt; 80–95% typical.
  • TEMPO/bleach (NaOCl, pH ~9) in biphasic CH2Cl2/H2O with KBr; 80–90%.
• Oxidation to heptanoic acid:
  • Jones (CrO3/H2SO4, acetone, 0 °C → rt) or TEMPO/NaClO2/acetamide (Pinnick) from the aldehyde; 70–90%.
• Fischer esterification (to heptyl esters):
  • Carboxylic acid (1–2 eq), catalytic H2SO4 or p‑TsOH, reflux in toluene or neat with Dean–Stark; hours to overnight; 60–95% depending on volatility.
• Dehydration:
  • H2SO4 or POCl3/pyridine; 0 °C → reflux; gives heptenes (mixtures). Subsequent hydroboration–oxidation (BH3·THF then H2O2/NaOH) affords anti‑Markovnikov alcohols.

Solvent/handling notes for the deuterated OD variant:

• Use anhydrous conditions to preserve OD labeling during manipulations (dry glassware, inert atmosphere). Avoid protic or strongly acidic/basic media if the OD label must be retained for analysis.
• Drying prior to use: 3 Å molecular sieves or distillation under reduced pressure; verify dryness by Karl Fischer where relevant.

Safety and Handling

Authoritative guidance: Always consult the product’s SDS for definitive hazard classification, first‑aid, and regulatory information.

Item-specific GHS details from Product Data: Not specified for this item; refer to SDS.

General safety profile for medium‑chain primary alcohols (literature/analog information for 1‑heptanol):

• Likely hazards: Combustible liquid; causes skin and eye irritation; harmful if swallowed or inhaled at high concentrations. Avoid vapor/aerosol generation and prolonged skin contact.
• Typical precautionary measures:
  • Engineering controls: Use in a chemical fume hood with adequate ventilation.
  • PPE: Lab coat, safety glasses or face shield, and chemical‑resistant gloves (e.g., nitrile). Consider double‑gloving for extended contact.
  • Hygiene: Remove contaminated clothing, wash skin thoroughly after handling.
• Incompatibilities: Strong oxidizers (may form exothermic reactions); strong acids/bases can promote dehydration or rapid H/D exchange at the hydroxyl. Reactive acid halides/anhydrides form esters vigorously.
• Fire safety: Keep away from ignition sources and hot surfaces. Use CO2, dry chemical, or alcohol‑resistant foam to extinguish. Vapors may travel to a source of ignition.
• Spill response: Absorb with inert material (vermiculite, sand), contain, and dispose per local regulations. Prevent release to drains.
• First aid (general):
  • Skin/eye contact: Rinse with water for at least 15 minutes; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting unless instructed by medical personnel; seek medical attention.
• Isotope-specific note: The O–D proton is exchangeable; avoid aqueous handling if maintaining deuterium enrichment is necessary.

Solvent Selection

Use profile: 1‑Heptanol‑d is an amphiphilic, medium‑polarity, protic solvent/additive with a long aliphatic chain. The OD label makes it attractive when reducing 1H background or tracing exchange processes.

• Polarity/proticity (literature, 1‑heptanol):
  • Protic, hydrogen‑bond donor and acceptor; dielectric constant ~12–13.
  • Moderately polar head with significant hydrophobic tail; promotes microheterogeneous environments.
• Miscibility:
  • Partially miscible with water (low solubility ~3–4 g/L at 20–25 °C, literature); fully miscible with many organics (toluene, ethers, esters, chlorinated solvents) and with other alcohols.
• When to choose 1‑heptanol‑d:
  • As a deuterated co‑solvent/additive for NMR experiments where suppression of the OH proton signal is desired while maintaining hydrophobic/alcoholic properties.
  • To probe hydrogen‑bonding and H/D exchange kinetics at the hydroxyl via IR/Raman (O–D band separation) or 2H NMR.
  • In partitioning or membrane‑interaction studies where chain length matters but 1H background from the OH should be minimized.
• Alternatives and comparisons:
  • 1‑Octanol (more hydrophobic, higher logP) vs 1‑hexanol (more miscible with water); 2‑propanol (more polar/protic but much more volatile); tert‑butanol (hindered, different H‑bond profile). Deuterated analogues of these may be preferred depending on analytical constraints.
• Practical notes:
  • Dry before use if water‑sensitive or if maintaining OD enrichment is critical (molecular sieves; avoid acidic sieves which accelerate H/D exchange).
  • Consider inert‑gas blanket to limit atmospheric moisture uptake.

Storage and Reconstitution

• Storage conditions (item-specific): Store at −20 °C. Keep container tightly closed.
• Shipping: Shipped in ice chest with ice pads to limit thermal exposure.
• Handling to preserve OD labeling:
  • Open only in a low‑humidity environment; backfill headspace with inert gas (N2/Ar) after use.
  • Minimize exposure to water, acids, and bases to avoid rapid H/D back‑exchange at the hydroxyl.
• Container/materials: Store in compatible glass with PTFE‑lined cap to reduce permeation; avoid reactive metals and acid chlorides/anhydrides nearby.
• Stability: Primary alcohols are generally stable at −20 °C away from light/air. The OD isotopic label is chemically labile to exchange but the molecule itself is not especially air‑sensitive. No polymerization/peroxide issues are typical for saturated alcohols.
• Reconstitution/Preparation:
  • If solidification occurs at low temperature, warm gradually to ambient in a sealed container before opening to prevent moisture ingress, then mix thoroughly.
  • For anhydrous use, dry over activated 3 Å molecular sieves or distill under reduced pressure; verify dryness by KF if critical.
• Freeze–thaw: Repeated freeze–thaw is acceptable for neat liquids, but limit unnecessary cycles to reduce headspace exchange and moisture uptake. Aliquot under inert atmosphere for critical isotopic applications.
• Research Use Note: For research use only.

Structure and Identity

Brief description: 1‑Heptanol‑d is the deuterium-labeled analogue of the straight-chain primary alcohol 1‑heptanol in which the hydroxyl proton is replaced by deuterium (O–D). Useful as an isotopic tracer and NMR/neutron-scattering compatible solvent/additive.

• Product name: 1-Heptanol-d (isotopologue with O–D)
• CAS: 1219804-99-5
• SKU: H1451093
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Note: for the OD isotopologue the formal formula is commonly written C7H15DO.)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature estimate: ~117.21 g/mol for the OD isotopologue vs 116.20 g/mol for protiated 1‑heptanol.)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet. (Typical non-isotopic 1‑heptanol SMILES: CCCCCCCO; OD isotopologues may be encoded with [2H] on O–D.)
• Structural features (descriptive):
  • Linear C7 aliphatic chain (n‑heptyl) terminated by a primary alcohol functional group.
  • One exchangeable deuterium at the hydroxyl (O–D). No stereocenters; achiral, acyclic, saturated hydrocarbon backbone.
  • Functional group: primary alcohol (–CH2–OH in protiated form; –CH2–OD here). Capable of hydrogen bonding (donor and acceptor), with amphiphilic character (polar head, hydrophobic tail).
• 2D structure (in words): A seven‑carbon unbranched chain with the hydroxyl group at carbon-1; the terminal –OD group attached to a methylene (–CH2–) at one end and a –(CH2)5–CH3 chain extending from the other end.

Synthetic Utility

Functional group: primary alcohol at C‑1 of a linear C7 chain. Key reactivity modes (literature/general):

• Activation to leaving groups:
  • Sulfonate esters (e.g., heptyl tosylate/mesylate) enable SN2 substitution to access 1‑heptyl amines, thioethers, azides (→ amines), nitriles (→ acids/amines), and halides.
  • Halogenation with PBr3, PCl3, SOCl2 (with pyridine/DMF catalysts as needed) to 1‑bromo/1‑chloroheptane—useful alkylating agents and coupling partners.
• Oxidation state manipulation:
  • PCC, Swern, or Dess–Martin to heptanal; TEMPO/bleach or Pinnick to heptanoic acid. Subsequent derivatizations (e.g., amidation, esterification) extend utility.
• Esterification:
  • Fischer conditions (catalytic acid, Dean–Stark) or DCC/EDC for sensitive substrates to give heptyl esters (hydrophobic protecting/solubilizing groups).
• Dehydration/elimination:
  • Acid‑catalyzed dehydration to heptenes; hydroboration–oxidation, epoxidation, or halofunctionalization expands access to regio‑/stereodefined derivatives.
• Ether formation (Williamson):
  • Generate heptyloxide under basic conditions (NaH/Na/K) then alkylate; or use heptyl sulfonate/halide with alcoholates/phenolates.

Isotope-specific considerations:

• The –OD deuteron is labile; under most reaction conditions (especially acidic/basic or in protic media), it exchanges with protium and will not be retained in products. For carbon‑skeletal deuteration, choose C‑deuterated heptanols or downstream labeling strategies.

Target Specificity

Not applicable. This product is a small‑molecule chemical reagent (deuterated primary alcohol) and does not possess antibody/oligonucleotide target specificity, clone identity, isotype, or species reactivity.