3,7-dimethyloctanal - Reagent grade

Cat. No.: D483461

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

Reagent grade

Storage

Room temperature

Note

Reagent Grade

Application Protocols

• Not applicable as a validated bioassay reagent.
• No tested applications (e.g., WB, IHC, IF, FC) or recommended dilutions are provided for this small-molecule aldehyde. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

• Applicability
  • 3,7-dimethyloctanal is a small organic aldehyde used in chemical research and fragrance chemistry. It is not a biomolecule per se; the following notes provide general biochemical context and do not imply biological/clinical use.
• General biochemical context (literature/general)
  • Aldehydes are reactive intermediates in metabolism (e.g., lipid peroxidation products), but 3,7-dimethyloctanal itself is typically encountered as a synthetic or fragrance-related compound rather than an endogenous metabolite.
  • As a saturated analogue of citronellal (a monoterpene aldehyde found in essential oils), it can interact with odorant receptors, serving as an odorant in sensory studies; such interactions are generally reversible and noncovalent.
  • In biological matrices, aldehydes can form Schiff bases with primary amines (e.g., lysine residues) and hydrate in aqueous environments; these reactions underpin common derivatization strategies in analytical biochemistry (DNPH assays, oxime formation).
• Laboratory handling in bio-related experiments
  • Poor water solubility necessitates co-solvents (EtOH, DMSO, or surfactants) at low percentages to avoid perturbing biological systems.
  • Reactive carbonyl can lead to nonspecific modification of proteins or amines; include appropriate controls and quench strategies (e.g., excess glycine) when exposure to biomolecules is unintended.
• Note: No medical or therapeutic claims are made. For research use only (per Product Data).

Buffer Applications

• Not typically applicable.
• Rationale: 3,7-dimethyloctanal is a hydrophobic aldehyde reagent, not a buffering agent. It does not provide acid/base conjugate pairs necessary for pH control in aqueous systems.
• Practical note: If used in biochemical assays, dissolve in a compatible co-solvent (e.g., ethanol or DMSO) and add to pre-made buffers at low percentages to maintain buffer integrity.

Green Alternatives

• Context
  • As a substrate, 3,7-dimethyloctanal itself is not readily substitutable when its specific structure is required. Greener choices focus on solvent selection, reagent choice, and sourcing.
• Greener sourcing (literature/general)
  • Bio-based feedstocks: This aldehyde can be prepared by hydrogenation of naturally derived citronellal (from citronella or lemongrass oils), supporting renewable content in synthesis campaigns.
• Greener media and reagents (general)
  • Prefer 2-MeTHF or CPME over THF/Et2O for organometallic additions when compatible; they offer improved safety (higher bp/flash point, lower peroxide rate) and can be sourced from biomass.
  • Use ethanol or water/ethanol mixtures for reductive amination; employ solid acid catalysts for acetalization to reduce mineral acid waste.
  • Catalytic oxidations: TEMPO/bleach in biphasic systems or O2 with nitroxyl catalysts as alternatives to chromium(VI) reagents.
• Illustrative comparison (general; not product specification) | Aspect | Conventional | Greener option | Trade-offs | | --- | --- | --- | --- | | Ether solvent for Grignard | THF/Et2O | 2-MeTHF/CPME | Different coordination/solubility; reoptimize conditions | | Oxidation to acid | Jones/PCC | TEMPO/NaClO or O2/nitroxyl | Selectivity control needed; halide management | | Reductive amination | NaBH3CN (MeOH) | H2/Pd in EtOH or formate reduction | Equipment/catalyst handling; hydrogen safety |
• Waste minimization
  • Distill/recover high-boiling solvents (toluene, 2-MeTHF); apply in-line drying and micro-scale flow to reduce solvent usage.

Pharmaceutical Uses

• Scope and limitations
  • This product is for research use only (per Product Data). No medical or clinical uses are claimed.
• Formulation-related roles (literature/general)
  • As an aroma ingredient, 3,7-dimethyloctanal (dihydrocitronellal) may be encountered as a fragrance/flavor component in non-sterile consumer products and could be used as a sensory excipient in topical or oral-care formulations under appropriate regulatory frameworks. Such uses require compliance with applicable standards (e.g., IFRA, FEMA/GRAS when relevant) and are outside the scope of this listing.
• Manufacturing/analytical relevance
  • Useful as a carbonyl standard for method development (GC, HPLC after derivatization) and as a synthetic intermediate en route to excipients (e.g., surfactants, emulsifiers) in a GMP environment, subject to quality system controls.
• Pharmacopeial status
  • No specific pharmacopeial monograph identified for 3,7-dimethyloctanal (literature/general). For any regulated use, specification setting and validation are required.

Physical Properties

• Item-specific (from Product Data)
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/typical properties for 3,7-dimethyloctanal (reference only; not product specification)
  • State/odor: Colorless to pale liquid; characteristic citrus/green odor (fragrance chemical) (literature/general).
  • Boiling point: ~205–210 °C at 101 kPa (literature)
  • Melting point: typically below 0 °C (remains liquid at room temperature) (literature)
  • Density: ~0.83–0.85 g/mL at 20–25 °C (literature)
  • Refractive index (nD20): ~1.440–1.450 (literature)
  • Vapor pressure: low at 25 °C (on the order of 0.01–0.1 kPa) (literature)
  • Water solubility: very low (<1 g/L); practically insoluble (literature)
  • Solubility: miscible with common organic solvents (alcohols, ethers, esters, hydrocarbons) (literature)
  • LogP (octanol/water): ~3.3–3.8 (estimated/literature)
  • pKa: not applicable (no ionizable protic functionality; aldehydic acidity negligible) (general)
• Notes
  • Values above are for general guidance only and may vary by source. For lot-specific specifications (e.g., density range, refractive index), consult the CoA/Spec Sheet.

Quality and Grades

• Item-specific (from Product Data)
  • Grade: Reagent Grade
• What Reagent Grade signifies (general)
  • Reagent Grade typically indicates suitability for general laboratory synthesis and analytical sample preparation where ultra-trace impurities and low-UV background are not critical. It is appropriate for routine organic synthesis, derivatizations, and method development.
• Implications for this item
  • For carbonyl chemistry (e.g., Grignard additions, imine formation), trace water and acids/bases can affect outcomes. While Reagent Grade is generally acceptable, users performing moisture-sensitive or spectroscopically demanding work (e.g., kinetic studies by UV) may wish to further dry/purify (e.g., molecular sieves, distillation) and verify purity by GC or NMR.
  • Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. If stabilizers are absent, aldehydes can slowly oxidize—consider inert-atmosphere storage once opened.
• Documentation
  • For exact impurity limits (water, residual solvents, metal content, UV cutoffs), refer to the CoA/Spec Sheet for this SKU (Not specified for this item).

Reaction and Applications

• Role: Branched aliphatic aldehyde useful in fragrance chemistry and as a building block in organic synthesis (literature/general). Research use only (per Product Data).
• Representative transformations (literature/general)
  • Nucleophilic carbonyl addition: Grignard/organolithium reagents afford tertiary/secondary alcohols; stereochemical outcomes governed by substrate approach to the prochiral carbonyl.
  • Reductive amination: With primary/secondary amines and reducing agents (e.g., NaBH3CN, H2/Pd), gives 3,7-dimethyloctylamines (odorant intermediates, surfactant precursors).
  • Oxime/hydrazone formation: Useful for derivatization and purification; facilitates analytical confirmation.
  • Acetalization: Protection as dimethyl/diethyl acetal using alcohols and acid catalysts (e.g., p-TsOH) enables downstream chemistry without carbonyl reactivity.
  • Oxidation: To 3,7-dimethyloctanoic acid via Pinnick oxidation (NaClO2) or TEMPO-mediated systems; to aldehyde hydrates in aqueous media.
  • Reduction: To 3,7-dimethyloctanol with NaBH4 (via acetal/hydride pathways) or catalytic hydrogenation.
  • Wittig/Horner–Wadsworth–Emmons: Installation of terminal or internal alkenes for access to citronellal analogues and terpene derivatives.
• Practical tips (general)
  • Minimize self-aldol: Run reactions at low temperature, under inert gas, and consider use of amine salts or preformed enamines for cross-aldol selectivity.
  • Drying: For water-sensitive reactions, pre-dry by passing through basic alumina or stirring over 3 Å molecular sieves; distillation under reduced pressure can improve color and remove peroxides (not typical) and low boilers.
  • Analysis: Monitor by GC-FID or GC-MS; aldehydes respond well to DNPH derivatization for HPLC/UV detection.

Reaction Conditions

• General conditions (literature guidance; not product specifications)
  • Grignard addition: RMgX (1.1–1.5 equiv) in dry Et2O or THF, 0 °C to rt, 1–4 h; quench with NH4Cl. Typical isolated yields 70–90% for secondary alcohols with simple alkyl/aryl reagents.
  • Organolithium addition: RLi (1.1 equiv) in THF at −78 to 0 °C, 0.5–2 h; careful temperature control to suppress over-reduction.
  • Reductive amination: Amine (1.1–1.5 equiv), AcOH (0.2–0.5 equiv), NaBH3CN or NaBH(OAc)3 in MeOH/CH2Cl2 or MeCN, 0 °C to rt, 2–16 h; or H2 (1–5 bar), Pd/C in EtOH, rt–50 °C. Typical yields 60–90% depending on amine sterics.
  • Oxime formation: NH2OH·HCl (1.2 equiv), pyridine or NaOAc in EtOH/H2O, rt–60 °C, 1–4 h; near-quantitative conversion by TLC/GC.
  • Acetalization: ROH (excess), catalytic p-TsOH or Amberlyst-15, Dean–Stark in toluene or under molecular sieves, 40–110 °C, 2–6 h.
  • Oxidation to acid: TEMPO (1–5 mol%), NaClO (1.1–1.5 equiv as active chlorine) in MeCN/H2O with buffer (pH ~8–9), 0–25 °C; or Pinnick oxidation (NaClO2/NaH2PO4, t-BuOH/H2O), 0–25 °C.
• Analytical/monitoring
  • GC-FID/GC-MS suitable due to volatility; derivatize to oxime for HPLC-UV. IR: strong C=O ~1725 cm−1; 1H NMR: aldehyde proton ~9.5–10 ppm (literature/general).
• Workup tips
  • Quench nucleophilic additions at low temperature; wash with bicarbonate to remove acids; bisulfite adduct formation can be used for purification/temporary protection but may be reversible slowly for branched aldehydes.

Safety and Handling

• Item-specific hazard information (from Product Data)
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.
• General safety profile for aliphatic aldehydes (literature/general; not product specification)
  • Hazards: Can be irritating to skin, eyes, and respiratory tract; may cause sensitization in susceptible individuals; harmful if swallowed in large quantities.
  • Flammability: Combustible liquid; keep away from ignition sources. Flash point for similar C10 aldehydes is often in the 70–95 °C range (literature).
• Handling recommendations
  • PPE: Wear lab coat, nitrile gloves, chemical splash goggles. Use in a fume hood to minimize inhalation of vapors.
  • Incompatibilities: Avoid strong oxidizers (risk of exothermic reaction), strong bases (aldol condensation/polymerization), strong reducing agents, and nucleophiles that may add to the carbonyl.
  • Special risks: Aldehydes can undergo air oxidation to acids; minimize air exposure. Peroxide formation is not a typical concern for aldehydes (contrast with ethers).
• First-aid overview (general)
  • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
  • Skin/eye contact: Rinse thoroughly with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Always consult the SDS for authoritative, product-specific safety information.

Solvent Selection

• Applicability
  • 3,7-dimethyloctanal is a hydrophobic, moderately high-boiling aliphatic aldehyde. It is used as a reagent/substrate rather than as a bulk solvent. Solvent selection here refers to choosing media for reactions or handling involving this aldehyde.
• Solubility/miscibility profile (literature/general)
  • Highly soluble in nonpolar and moderately polar organic solvents: hexanes/heptane, toluene, diethyl ether, MTBE, THF, DCM, ethyl acetate, lower alcohols.
  • Practically insoluble in water.
• Polarity and dielectric considerations (general)
  • Low polarity substrate; best handled in low- to medium-polarity solvents. For nucleophilic additions (e.g., Grignard), ethereal solvents (Et2O, THF) are typical. For condensations (oxime/hydrazone, imines), alcohols, toluene, or acetonitrile with acid catalysis may be used.
• Selection guidance by use-case
  • Carbonyl additions (Grignard/organolithium): dry Et2O or THF; maintain anhydrous, inert conditions.
  • Reductive amination: alcohols (MeOH/EtOH/iPrOH) or aprotic polar solvents (MeCN), with hydrogenation catalysts or borohydride/cyanoborohydride systems.
  • Oxidation to acid: biphasic aqueous-organic (e.g., AcOEt/NaClO2 buffer) or acetonitrile for TEMPO/bleach; control over-oxidation.
  • Aldol condensations: nonprotic solvents (THF, toluene) with base; suppress self-condensation by slow addition and low temperature.
• Quick comparison (general)
  • Hexanes: maximal hydrophobicity, easy workup; limited reagent solubility for polar catalysts.
  • Toluene: higher bp, good for thermal condensations.
  • THF/Et2O: ideal for organometallic additions; moisture sensitive.
  • Ethanol/MeOH: convenient for reductive amination; may participate in acetal/hemiacetal equilibria.

Storage and Reconstitution

• Item-specific (from Product Data)
  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• General guidance for aldehyde storage (literature/general)
  • Container: Store tightly sealed in amber glass to minimize light exposure; purge headspace with inert gas (N2 or Ar) after opening to limit oxidation to the corresponding acid.
  • Atmosphere: Keep under dry, inert atmosphere; avoid prolonged exposure to air and moisture which can lead to hydrate formation or aldol-type side reactions.
  • Temperature: Ambient storage is typically acceptable; refrigeration (2–8 °C) can further slow degradation for long-term keeping if material remains liquid and does not crystallize.
  • Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If no stabilizer is present, consider smaller containers to reduce repeated air exposure.
• Reconstitution/handling
  • The product is expected to be supplied neat (no reconstitution required). If preparing stock solutions, use dry, oxygen-poor solvents (e.g., anhydrous toluene, THF, or ethanol), label with preparation date, and store under inert gas at 2–8 °C when feasible.
• Shelf-life
  • For any lot-specific retest or expiry dating, consult the product label or CoA; not specified for this item.
• Research Use Note: For research use only (per Product Data).

Structure and Identity

• Item-specific (from Product Data)
  • SKU: D483461
  • Product name: 3,7-dimethyloctanal
  • Grade/Purity: Reagent Grade
  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/typical identity information (for reference only; not product specification)
  • Synonym: dihydrocitronellal (saturated analogue of citronellal)
  • Molecular formula: C10H20O (literature)
  • Molecular weight: 156.27 g/mol (literature)
  • Structural features: A linear, branched aliphatic aldehyde (C8 main chain with terminal –CHO; methyl substituents at C3 and C7). Functional group: terminal aldehyde; no stereocenters in the saturated aldehyde backbone as drawn, but chiral centers can arise depending on substitution pattern around C3 and C7 (literature/general).
  • 2D description in words: A terminal aldehyde carbonyl (–CHO) attached to a saturated, mostly linear C8 chain bearing a methyl branch at the third carbon from the aldehyde and another methyl branch near the distal end (at C7), yielding a branched decyl framework with one carbonyl oxygen (literature/general).

Synthetic Utility

• Functional group leverage
  • Terminal aldehyde enables diverse transformations: additions (M/M′), condensations, oxidations, reductions, and olefination (literature/general).
• Retrosynthetic value
  • Serves as a masked one-carbon electrophile to elaborate the C1 terminus of branched aliphatic frameworks. Wittig/HWE reactions convert it to alkenes that map back onto monoterpene scaffolds (e.g., citronellal/geraniol families after further steps).
• Building block applications (literature/general)
  • Access to 3,7-dimethyloctyl derivatives: alcohols (NaBH4), acids (Pinnick/TEMPO), amines (reductive amination), imines/enamines (for C–C bond formation via Mannich-type reactions).
  • Stereocontrol: Though the aldehyde center is prochiral, additions create new stereocenters. Chiral catalysts or auxiliaries (e.g., CBS reduction variants for related ketones, or chiral amines in imine formation) can be applied when enantioselectivity is required in downstream products.
• Protecting group strategies
  • Convert to acetals with diols (e.g., ethylene glycol) to mask reactivity during base-mediated steps; deprotect under mild aqueous acid.
• Process considerations
  • Branched chain reduces volatility vs linear C8 aldehydes, aiding handling and distillation. Control self-condensation by temperature management and slow feed in basic media.

Target Specificity

• Not applicable.
• This product is a small-molecule aldehyde reagent, not a biological targeting agent (e.g., antibody, ligand with defined target specificity). No antigen/epitope, species reactivity, clone, or isotype data are relevant.