(4-Hexylphenyl)hydrazine , CAS No.87065-18-7

CAS: 87065-18-7 Cat. No.: H1364030 Formula: C₁₂H₂₀N₂ Peso molecolare: 192.3

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CCCCCCC1=CC=C(C=C1)NN
• IUPAC Name: (4-hexylphenyl)hydrazine
• InChIKey: HKEKJKIKMWCCDN-UHFFFAOYSA-N
• INCHI: 1S/C12H20N2/c1-2-3-4-5-6-11-7-9-12(14-13)10-8-11/h7-10,14H,2-6,13H2,1H3
• Peso molecolare: 192.3

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Phenylhydrazines

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Phenylhydrazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylhydrazines
• Alternative Parents: Organopnictogen compounds Hydrocarbon derivatives Hydrazines and derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenylhydrazine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Hydrazine derivative - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenylhydrazines. These are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 192.300 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 192.163 Da
• Monoisotopic Mass: 192.163 Da
• Topological Polar Surface Area: 38.100 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 128.000
• 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.

• No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, see the sections on Reaction Conditions and Application notes under Reaction & Applications.

Biological Roles

Applicability

• This product is a synthetic arylhydrazine. It is not known as a natural metabolite or cofactor.

General biochemical context (literature; not medical/clinical)

• Reactivity toward carbonyls: Hydrazines can form covalent adducts (hydrazones) with aldehyde/ketone groups present in biomolecules or model substrates. This chemistry underlies certain analytical derivatizations (e.g., labeling of carbonyl-containing metabolites) but also contributes to cellular toxicity in biological systems.
• Redox behavior: Hydrazines can participate in redox processes, generating nitrogen-containing radicals or diimide under oxidative conditions, which can perturb cellular redox balance in model studies.
• Structure–property note: The para-hexyl substituent increases hydrophobicity relative to phenylhydrazine, which may alter membrane partitioning and nonspecific binding in biochemical experiments.

Research-use only

• As indicated by the product data, this material is for research use only. Any exploration of biochemical interactions should be confined to in vitro or ex vivo chemical biology assays with appropriate containment and approvals. No clinical or diagnostic use is intended or implied.

Buffer Applications

Not typically applicable.

• (4-Hexylphenyl)hydrazine is a reactive organic building block, not a buffering agent. It does not constitute a defined conjugate acid/base pair suitable for preparing laboratory buffer systems.
• For practical use, refer instead to the sections on Reaction & Applications, Synthetic Utility, and Reaction Conditions for guidance on employing this reagent in organic media.

Green Alternatives

Greenness considerations (general)

• Hazard: Arylhydrazines are associated with toxicity and potential mutagenicity; handling risks are nontrivial. Process design should minimize operator exposure and waste.
• Solvent selection: Favor greener solvents (EtOAc, 2-MeTHF, CPME, bio-ethanol) where compatible with kinetics and selectivity.

Alternatives and trade-offs (literature/general)

• For carbonyl derivatization: Hydroxylamine or O-alkylhydroxylamines can replace hydrazines to make oximes; these are often less hazardous but alter downstream chemistry (e.g., Beckmann vs Wolff–Kishner pathways).
• For indole synthesis: Alternatives to Fischer indole (e.g., Bartoli, Larock, or metal-catalyzed annulations from anilines/alkynes) can avoid hydrazines but may require sensitive catalysts or harsher reagents.
• For azo colorants: Diazonium chemistry from anilines (via NaNO2/HCl) can be employed instead of arylhydrazines; however, diazonium salts pose their own safety concerns (thermal instability).

Compact comparison (qualitative)

• (4-Hexylphenyl)hydrazine: Strong carbonyl reactivity; direct route to 4-hexylindoles; toxicity and oxidation hazards; good nonpolar solubility.
• Hydroxylamine derivatives: Lower toxicity profile; different downstream transformations; sometimes lower reactivity toward hindered ketones.
• Aniline/diazonium routes: Avoid hydrazine handling; require low-temperature nitrosation and careful control of energetic intermediates.

Process tips

• Implement in-line or telescoped operations to limit isolation of hydrazine intermediates.
• Use closed systems, minimal headspace oxygen, and solvent recycling to reduce emissions and waste.

Pharmaceutical Uses

Context (no therapeutic claims)

• Arylhydrazines are not used as pharmaceutical excipients due to reactivity and toxicity concerns. However, they can serve as synthetic intermediates in process chemistry.

Potential roles (process development; literature/general)

• Intermediate to heterocycles: Via Fischer indole synthesis, (4-hexylphenyl)hydrazine can provide 4-hexylindole frameworks, which are common motifs in medicinal chemistry libraries and agrochemical leads.
• Carbonyl derivatization: Hydrazone formation can aid in purification or characterization of API intermediates bearing carbonyl groups.

Regulatory note

• There is no pharmacopeial monograph known for this specific compound. Any use in GMP environments would require full internal specifications, impurity profiling (including azo/azoxy species), and robust safety controls.

Reminder

• Research use only, as stated in the product data. No clinical or diagnostic application is implied.

Physical Properties

Item-specific specifications

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

Literature/computed (for context; not item-specific specs)

• Empirical formula (derived from structure): C12H20N2.
• Formula weight: ~192.31 g/mol (calculated from atomic weights).
• Acid–base behavior: Primary arylhydrazines are weak bases; pKa of the conjugate acid typically ~5–6 (literature, phenylhydrazine analogs). Electron-donating para-alkyl groups can slightly increase basicity.
• Polarity/solubility (qualitative): Amphiphilic. The hydrazino group imparts polarity and H-bonding; the n-hexyl chain imparts hydrophobicity. Expect good solubility in many organic solvents (alcohols, ethers, chlorinated, aromatics) and limited solubility in water (literature trend for para-alkyl arylhydrazines).
• Volatility: Low; arylhydrazines are typically low-volatility liquids/low-melting solids; thermal sensitivity possible (literature).

Do not treat these literature/computed values as specifications. For exact item properties (bp, mp, density, refractive index, water/peroxide/metal limits, UV cutoff), refer to the product’s CoA/Spec Sheet.

Quality and Grades

Item-specific information

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

Context and guidance (general)

• Hydrazines are air- and light-sensitive to varying degrees. Where applicable, suppliers may control dissolved oxygen and headspace or include antioxidants; any such measures will appear on the CoA/Spec Sheet if used.
• If an “AR,” “Reagent,” or “Synthesis” grade is indicated on the CoA, typical expectations are:
  • AR/Reagent: Suitable for most research syntheses; standard impurity controls.
  • High-purity/assay grades: Tighter controls on related aryl species (azo/azoxy), water, and residual solvents—important for moisture- or oxidation-sensitive reactions (e.g., diazotizations, Fischer indoles).
• For chromatography-critical uses (monitoring low-level byproducts), low UV-background solvent residues and minimal chromophoric impurities are preferred. Request UV cutoffs and trace impurity data as needed.

Recommendation

• Verify assay, identity (NMR/GC–MS/HPLC), and impurity profile (azo/azoxy content, water) on the CoA prior to use in sensitive transformations.

Reaction and Applications

Core reactivities of (4-hexylphenyl)hydrazine (literature/general)

• Hydrazone formation: Reacts with aldehydes and ketones to form hydrazones; useful for carbonyl protection, purification (crystalline derivatives), or as intermediates for further transformations (e.g., Wolff–Kishner-type reductions via diimide generation from appropriate systems).
• Fischer indole synthesis: Condenses with carbonyl compounds under acidic conditions to give 4-hexyl-substituted indoles—valuable motifs in materials, ligands, and bioactive scaffolds. Para-alkyl substituents often enhance solubility and influence regiochemistry in subsequent functionalizations.
• Diazotization/azo chemistry: Under nitrosating conditions at low temperature, arylhydrazines can form diazonium-like species or diazo intermediates that undergo azo coupling with activated aromatics to yield para-hexyl-azo dyes/pigments.
• Reductive transformations: Acts as a reducing agent in certain metal-catalyzed protocols; can form diimide in situ under oxidative conditions for selective alkene reductions (method dependent).

Practical tips

• Oxygen control: Minimize exposure to air/light to limit oxidative formation of azo/azoxy byproducts; degas solvents where feasible.
• Acid sensitivity: Strong acids promote Fischer indolization; if undesired, maintain neutral to mildly basic conditions during handling/derivatizations.
• Water removal: For hydrazone formation, drive equilibrium by azeotropic water removal (Dean–Stark in toluene/xylene) or molecular sieves in aprotic solvents.
• Stoichiometry: Use slight excess of hydrazine reagent to push condensation; remove excess by aqueous acid extraction if compatible.

Applications (manufacturer field was blank)

• Suitable as a building block for para-hexyl arylindoles, hydrazone derivatives for analytical characterization, and tailored azo materials with enhanced hydrophobicity.

Reaction Conditions

General literature guidance (not item-specific specifications)

• Hydrazone formation:
  • Conditions: Carbonyl (1.0 eq), (4-hexylphenyl)hydrazine (1.1–1.5 eq), catalytic acetic acid or p-toluenesulfonic acid.
  • Solvents: EtOH, i-PrOH, THF, DCM, or toluene.
  • Temperature/time: 20–80 °C, 1–16 h depending on substrate; water removal (molecular sieves or Dean–Stark) improves conversion.
  • Workup: Quench with base if acid used; extract into organic; wash and dry; purify by chromatography on neutral alumina/silica.
• Fischer indole synthesis:
  • Conditions: Preformed hydrazone or in situ condensation with ketone/aldehyde; strong Brønsted acid (AcOH/HCl, polyphosphoric acid, or Lewis acid variants).
  • Solvents: AcOH, EtOH, DCE, or solvent-free in melt conditions for robust substrates.
  • Temperature/time: 80–140 °C, 2–12 h. Monitor by TLC/LC–MS.
  • Notes: Para-alkyl substitution generally tolerated; control acid strength to avoid over-oxidation.
• Diazotization/azo coupling:
  • Diazotization: 0–5 °C, NaNO2 in mineral acid (HCl/H2SO4) or nitrosyl reagents; maintain low temperature to control exotherm/NOx.
  • Coupling: Phenols/anilines in mildly basic aqueous/alcoholic media (pH 8–10) at 0–20 °C.
  • Safety: Vent properly; avoid accumulation of energetic intermediates; perform small-scale trials first.

Typical outcomes

• Hydrazones: Often 70–95% isolated yield for unhindered aldehydes; sterically hindered ketones lower.
• Fischer indolization: 40–85% depending on substrate and acid system.
• Azo coupling: Variable (30–80%) depending on coupling partner and conditions.

Always optimize on small scale and consult primary literature for your specific substrate class.

Safety and Handling

Item-specific hazard 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 arylhydrazines (literature; consult SDS for authoritative guidance)

• Hazards: Toxic if swallowed/inhaled; skin/eye irritant; may cause methemoglobinemia; suspected mutagenic potential. Combustible. Can undergo air-oxidation to azo/azoxy species; may darken on storage.
• PPE: Lab coat, nitrile gloves (change regularly), splash goggles. Use in a fume hood to control vapors and potential NOx during diazotization.
• Handling: Avoid heat, sparks, and open flame. Minimize exposure to air and light to reduce oxidation; keep containers tightly closed. Avoid contact with oxidizers and nitrosating agents except under controlled reaction conditions.
• Incompatibilities: Strong oxidizers; strong acids plus nitrite (uncontrolled diazotization with NOx evolution); strong electrophiles; copper and some metal salts may catalyze oxidation.
• First aid (overview): Inhalation—move to fresh air; Skin/Eye—rinse with water for 15 min; Ingestion—rinse mouth, do not induce vomiting. Seek medical attention in all exposure scenarios. Provide SDS to responders.
• Spill/Fire: Absorb small spills with inert material; avoid oxidizing absorbents. For fire, use dry chemical, CO2, or foam; water spray to cool containers. Combustion may produce NOx.

Always defer to the product-specific SDS for definitive hazard classifications and response procedures.

Solvent Selection

Applicability

• This product is a reactive arylhydrazine reagent rather than a solvent. Solvent selection considerations below are for using (4-hexylphenyl)hydrazine in synthesis.

Solubility and polarity (general trends)

• Mixed character: A hydrazino group (hydrogen bonding donor/acceptor) paired with a hydrophobic n-hexyl chain and aromatic ring.
• Expected solubility: Good in ethanol, isopropanol, methanol (caution: reactivity), THF, dioxane, ethyl acetate, dichloromethane, chloroform, toluene, and other aromatics. Limited in water.

Choosing solvents by application (literature guidance)

• Hydrazone formation with carbonyls: Alcohols (EtOH), aprotic ethers (THF), or chlorinated solvents (DCM) with catalytic acid; remove water to drive equilibrium (Dean–Stark in toluene for ketones/aldehydes with heating).
• Fischer indole synthesis: Protic acids in high-boiling solvents (AcOH, EtOH, EtOH/HCl, HOAc/MeSO3H) or polyphosphoric acid media; or Lewis acid in non-protic solvents for sensitive substrates.
• Diazotization/azo coupling: Aqueous-organic biphasic or alcoholic media at low temperature (0–5 °C) for diazotization; coupling often in mildly basic aqueous/alcoholic solutions.

Comparison pointers

• Versus phenylhydrazine: Increased lipophilicity improves solubility in nonpolar media and can benefit phase behavior in biphasic systems.
• Versus more polar arylhydrazines (e.g., p-aminophenylhydrazine): Lower water solubility reduces loss to aqueous phases but may require co-solvents for aqueous workups.

Storage and Reconstitution

Item-specific directions

• Storage Conditions: Room temperature (per Product Data).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for arylhydrazines (literature/best practice)

• Protection: Store tightly sealed under inert gas (nitrogen/argon) if possible, protected from light to limit oxidative discoloration and formation of azo/azoxy byproducts.
• Environment: Keep in a dry place; avoid humid air. Desiccant in the outer container can help maintain low moisture.
• Containers: Use amber glass with PTFE-lined caps. Avoid reactive metals.
• Stability: Hydrazines can slowly oxidize on standing; monitor by TLC/LC–MS. If discoloration occurs, consider purification or use freshly distilled/repurified material for sensitive reactions.
• Reconstitution: If supplied as a solid or viscous oil, dissolve in a dry, oxygen-free solvent (e.g., anhydrous EtOH, THF, DCM, or toluene) immediately before use. Degas via inert sparge if needed for oxidation-sensitive steps.

Note

• Follow the product label and SDS for any additional, item-specific storage and handling instructions. Research use only, as stated in the Product Data.

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: H1364030
• Product Name: (4-Hexylphenyl)hydrazine
• CAS: 87065-18-7
• InChIKey: 123689 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

General structural description (literature/computed)

• Core scaffold: A monosubstituted phenylhydrazine bearing a para n-hexyl substituent.
• Functional groups: Aromatic ring; an anilide-type hydrazino substituent (–NH–NH2) directly bound to the phenyl ring; linear n-hexyl chain at the para position relative to –NH–NH2.
• Molecular formula (derived from name; literature/computed): C12H20N2.
• Molecular weight (literature/computed): ~192.31 g/mol.
• 2D structure in words: A benzene ring substituted at C1 with a hydrazino group (–NH–NH2) and at C4 with a straight-chain hexyl group (–(CH2)5–CH3), giving a para relationship between the two substituents.

Notes

• The above formula/MW are provided as literature/computed values based on the chemical name; confirm against the product CoA for item-specific specifications.

Synthetic Utility

Key functionalities

• Arylhydrazine motif (–Ar–NH–NH2): Nucleophilic at terminal nitrogen; condenses with carbonyls; can be transformed under nitrosating/oxidative conditions.
• Para n-hexyl substituent: Electron-donating inductive effect; increases lipophilicity and can modulate electronic density on the ring, subtly affecting reaction rates and regioselectivity in electrophilic processes.

Typical transformations (literature)

• Hydrazone formation with aldehydes/ketones (mild acid catalysis). Hydrazones serve as handles for:
  • Fischer indolization to form 4-hexylindoles.
  • Reductive cleavage or Wolff–Kishner-type reductions (depending on substrate/system).
• Diazotization under NaNO2/HCl at 0–5 °C leading to azo coupling partners; useful for hydrophobic azo dyes/pigments.
• N–N functionalization: Acylation or sulfonylation at nitrogen to modulate stability/reactivity; N-protection can direct selectivity in subsequent steps.

Retrosynthetic value

• As a para-alkyl arylhydrazine, it enables direct mapping of the hexyl group into heteroaromatic products (indoles), streamlining routes to lipophilic scaffolds without late-stage alkylation.

Practical considerations

• Control oxidation: Use degassed solvents and minimal headspace oxygen; consider antioxidants or immediate consumption in telescoped sequences.
• Purification: Avoid strong acid silica; use neutral/alumina or buffered systems to limit decomposition and tailing of polar hydrazino species.

Target Specificity

Not applicable.

• This product is a small-molecule arylhydrazine and does not possess biological target specificity parameters such as antigen/epitope, species reactivity, clone, or isotype. No antibody- or probe-specific data are associated with this listing.