4-Fluorocyclohexanecarbaldehyde - ≥98% , CAS No.1554041-53-0

CAS: 1554041-53-0 Cat. No.: F978420 Summenformel: C₇H₁₁FO Molekulargewicht: 130.160 EG-Nummer: 824-850-4

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

• Kanonisches Lächeln: C1CC(CCC1C=O)F
• IUPAC Name: 4-fluorocyclohexane-1-carbaldehyde
• InChIKey: OQRSBWCLDGFKRY-UHFFFAOYSA-N
• INCHI: 1S/C7H11FO/c8-7-3-1-6(5-9)2-4-7/h5-7H,1-4H2
• Molekulargewicht: 130.160

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organohalogen compounds
    • Klasse Alkyl halides
      • Subclass Cyclohexyl halides

• Kingdom: Organic compounds
• Superclass: Organohalogen compounds
• Klasse: Alkyl halides
• Subclass: Cyclohexyl halides
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclohexyl halides
• Alternative Parents: Organofluorides Organic oxides Hydrocarbon derivatives Alkyl fluorides Aldehydes
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexyl halide - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organofluoride - Carbonyl group - Alkyl fluoride - Aldehyde - Aliphatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 130.160 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 130.079 Da
• Monoisotopic Mass: 130.079 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 95.100
• 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

• No validated bioassay protocols (WB, IHC, IF, FC) apply to this reagent. It is a synthetic intermediate for chemical transformations.
• Representative synthetic procedures are provided as general guidance under Reaction Conditions and Reaction & Applications. Always adapt conditions to your specific substrates and consult primary literature.
• Research Use: For research use only.

Biological Roles

• Applicability note: This product is a small-molecule synthetic building block. It is not a biological buffer, enzyme, protein, or metabolite standard in our catalog entry.
• General context (literature)
  • Fluorinated cycloalkyl motifs are widely used in medicinal chemistry to modulate lipophilicity, metabolic stability, and conformational preferences. The 4-fluorocyclohexyl group can influence pKa of neighboring functionalities and reduce oxidative metabolism on the ring.
  • Aldehyde functionality is typically masked (as imines/oximes/acetals) or converted (e.g., to amines/alcohols/acids) prior to biological testing; parent aldehydes may be reactive toward biomolecules and are seldom used directly in biological systems.
• No specific endogenous role is associated with 4-fluorocyclohexanecarbaldehyde. Any use should be confined to research and in vitro synthetic derivatization prior to bioevaluation.

Buffer Applications

• Not typically applicable. 4-Fluorocyclohexanecarbaldehyde is a reactive organic aldehyde used in chemical synthesis, not as a buffering agent or pH control reagent.
• For laboratory workflows involving this aldehyde, select an appropriate organic solvent system (see Solvent Selection) rather than aqueous buffer systems. If aqueous conditions are required (e.g., biphasic oxidations), use standard buffers only to control pH of the aqueous phase; the aldehyde itself does not contribute buffering capacity.

Green Alternatives

• Greener solvent choices (general guidance)
  • Replace chlorinated solvents (DCM, CHCl3) with 2-MeTHF, EtOAc, or CPME where feasible for reductive amination, imine formation, and Wittig/HWE reactions.
  • For organometallic additions, 2-MeTHF often substitutes for THF/Et2O with similar reactivity and better safety/renewability profile.
• Greener reducing systems for reductive amination
  • Swap NaBH3CN (cyanide-containing) for NaBH(OAc)3 in acetic acid media, or use catalytic hydrogenation (H2/Pd or transfer hydrogenation with HCO2NH4/Ir–Ru catalysts) to minimize hazardous waste.
• Oxidations
  • Use Pinnick oxidation (NaClO2 with H2O2 scavengers) in aqueous media instead of chromium(VI) reagents to reach the carboxylic acid.
• Workup/waste minimization
  • Favor liquid–liquid extractions with EtOAc/IPA–water pairs; recover and recycle solvents where possible.
  • Employ molecular sieves rather than azeotropic reflux for water removal when energy conservation is a priority.
• Quick comparison (illustrative)
  • THF vs 2-MeTHF: Similar polarity and organometallic compatibility; 2-MeTHF has higher boiling point and can be bio-based; phase separation aids workups.
  • DCM vs EtOAc: EtOAc is biodegradable and less toxic; may require temperature/stoichiometry adjustments to match reaction rates.
• Note: Verify reaction-specific performance when switching media; minor changes in solvation can affect selectivity with aldehydes.

Pharmaceutical Uses

• No medical or clinical claims. This product is offered strictly for research use.
• General formulation/manufacturing context (literature)
  • As a building block, 4-fluorocyclohexanecarbaldehyde can be transformed into amines, alcohols, acids, or heterocycles that serve as intermediates en route to APIs or tool compounds. The 4-fluorocyclohexyl motif is valued for modulating permeability and metabolic stability.
  • Direct use as an excipient is not typical for reactive aldehydes due to incompatibility with amines and other nucleophiles in formulations.
  • Regulatory status: No pharmacopeial monograph is expected for this specialized research intermediate. GMP sourcing would require separate qualification if intended for drug-substance manufacturing campaigns.

Physical Properties

• Item-specific (Product Data)
  • 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 (reference information; not item-specific specs)
  • Physical state: expected to be a colorless liquid at ambient temperature (by analogy to cyclohexanecarbaldehyde and halo-substituted analogs).
  • Boiling point: aldehydic cyclohexane derivatives typically boil in the ~170–210 °C range; 4-fluoro substitution modestly increases bp relative to cyclohexanecarbaldehyde (literature/analogy estimate).
  • Melting point: likely below room temperature (literature/analogy for related cyclohexyl aldehydes).
  • Density: aliphatic aldehydes ~0.90–1.05 g/mL at 20 °C; a single F may raise density slightly (literature/analogy).
  • Refractive index: aliphatic aldehydes commonly n20 D ~1.44–1.48 (literature/analogy).
  • Solubility: low in water; miscible with common organic solvents (Et2O, THF, DCM, toluene, MeCN, alcohols) (general chemical knowledge).
  • Partitioning: cLogP for cyclohexyl aldehydes typically ~1.8–2.5; a fluoro substituent often modestly increases lipophilicity (estimated/computed trend).
  • Functional reactivity: typical for non-enolizable aldehydes at the carbonyl carbon; the ring bears one F (inductive –I) which slightly increases electrophilicity (general chemical knowledge).
• Note: Values above are for context only; consult the item’s CoA/SDS for measured specifications and safe handling parameters.

Quality and Grades

• Item-specific (Product Data)
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Guidance on grades for this compound class (general)
  • Research or synthetic grade: Suitable for most organic synthesis (imine formation, Grignard additions, reductive amination). Verify carbonyl integrity (e.g., GC, NMR) prior to moisture/air-sensitive steps.
  • High-purity/low-water specifications (if offered): Beneficial for moisture-sensitive reactions (organometallic additions, Wittig/ HWE). Low UV-absorbing grades are generally unnecessary unless the aldehyde is used as a GC/HPLC analyte or for photophysical studies.
  • Stabilizers: Aliphatic aldehydes are typically shipped without stabilizers; some suppliers may add trace acid or antioxidant inhibitors. If present, stabilizers can influence base-catalyzed reactions (e.g., aldol). Always check the CoA for any inhibitor and remove if necessary (e.g., short-path distillation under reduced pressure).
  • Analytical QC suggestions (user-side):
    • Check for over-oxidation to the corresponding carboxylic acid by 1H NMR (acidic OH, aldehydic proton ~9–10 ppm) and GC.
    • Water content by Karl Fischer if the reaction is moisture-sensitive.
    • Peroxide testing is generally not relevant to aldehydes (more relevant to ethers).

Reaction and Applications

• Role: Fluorinated alicyclic aldehyde used as an electrophilic building block. The para (4-) fluoro substituent tunes electronics and lipophilicity without adding synthetic handles, making it attractive for SAR in medicinal and agrochemical discovery.
• Representative transformations (literature/general)
  • Reductive amination with primary/secondary amines → 4-fluorocyclohexylmethyl amines; reagents: NaBH(OAc)3, NaBH3CN, or catalytic hydrogenation of imines.
  • Nucleophilic additions: Grignard/organolithium to give secondary alcohols; cyanide to give cyanohydrins; bisulfite addition for purification handles.
  • Carbon–carbon bond formation: Wittig/HWE olefination to give 4-fluorocyclohexyl-substituted alkenes; Henry (nitroaldol) reactions with nitroalkanes; aldol reactions as electrophile.
  • Derivatizations: Oxime/hydrazone formation for characterization or as protected forms; acetalization (e.g., ethylene glycol) for protection; oxidation to carboxylic acid (e.g., Pinnick) or to 4-fluorocyclohexanecarboxylic acid derivatives.
  • Asymmetric variants: Enantioselective additions (e.g., organocatalytic proline-catalyzed aldol with ketones; chiral catalysts for transfer hydrogenation of imines derived from this aldehyde).
• Practical tips
  • Handle under inert atmosphere for moisture/air-sensitive steps; aldehydes can oxidize to acids during storage and workup.
  • Use molecular sieves (3Å/4Å) or Dean–Stark to drive imine/oxime formation.
  • For reductive amination, control pH (AcOH or TFA catalytic) to balance imine formation vs over-reduction.
  • The ring C–F bond is robust; nucleophilic displacement at sp3–C–F is unlikely under standard conditions, preserving the fluorine through multistep sequences.
  • Purification: Short-path distillation under reduced pressure or flash chromatography; bisulfite adduct crystallization can aid in impurity removal.

Reaction Conditions

• General guidance (literature; adjust per substrate and scale)
  • Reductive amination: Mix amine (1.1–1.5 eq) and aldehyde (1.0 eq) in DCM or MeOH with 3Å MS; add AcOH (0.2–0.5 eq) then NaBH(OAc)3 (1.5–2.5 eq) at 0–25 °C; stir 2–16 h. Typical isolated yields: 70–90% with clean substrates.
  • Imine formation: Toluene reflux with Dean–Stark or MeOH at rt with MS; catalytic p-TsOH (0.05–0.2 eq) can accelerate. Monitor by IR (C=N ~1660 cm−1) or 1H NMR.
  • Organometallic additions: Generate RMgX/RLi in Et2O/THF; add to a −78 to 0 °C solution of aldehyde under N2/Ar. Quench with saturated NH4Cl. Yields commonly 60–95% depending on nucleophile.
  • Wittig/HWE: For stabilized ylides, use THF or toluene, 0–25 °C; for non-stabilized ylides, DCM/THF at 0 °C to rt. Bases: NaHMDS, t-BuOK, or n-BuLi as appropriate. Typical E/Z selectivity per ylide type.
  • Oxidations to acid: Pinnick (NaClO2, NaH2PO4 buffer, 2-methyl-2-butene as scavenger) in t-BuOH/H2O/MeCN at 0–25 °C; high chemoselectivity, 70–95%.
  • Oxime/hydrazone: Hydroxylamine·HCl or hydrazine with pyridine or AcOH, EtOH/MeOH, rt–reflux; 1–6 h.
• Workup/purification
  • Standard aqueous workups; avoid prolonged basic washes that may induce aldol side reactions.
  • Purify by silica chromatography (eluent: hexanes/EtOAc) or short-path distillation under reduced pressure to minimize air exposure.

Safety and Handling

• Item-specific (Product Data)
  • GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
  • Storage: Room temperature (as provided).
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• General safety considerations for aliphatic aldehydes (literature/general guidance; defer to SDS)
  • Hazards: Many aldehydes are skin/eye irritants and may cause respiratory irritation or sensitization upon repeated exposure. Avoid inhalation of vapors and contact with skin/eyes.
  • PPE: Use chemical-resistant gloves (e.g., nitrile), safety goggles/face shield, lab coat; handle in a fume hood.
  • Incompatibilities: Strong oxidizers (risk of exothermic oxidation to acids), strong bases (aldol/self-condensation), strong nucleophiles (amines, hydrides, organometallics). Avoid prolonged exposure to air/moisture which can promote oxidation to carboxylic acid.
  • Reactivity notes: Carbonyl readily forms imines/oximes/hydrazones; undergoes nucleophilic additions (e.g., Grignard, organolithium); can be reduced to alcohols. The C–F bond is stable and not expected to participate in typical nucleophilic displacement.
  • First-aid overview: If on skin/eyes, rinse with water for ≥15 min; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always consult the SDS for authoritative instructions.
  • Fire: Combustible organic liquid; use CO2, dry chemical, or foam. Vapors may be irritating; fight fire with SCBA.
  • Spill response: Absorb with inert material, ventilate area, avoid ignition sources; dispose per regulations.

Solvent Selection

• Applicability note: This product is a reactive building block, not a bulk solvent. The following guidance addresses solvent choice when using this aldehyde in synthesis.
• General solvent compatibility (general chemistry knowledge)
  • Miscible with common organic solvents (Et2O, THF, DCM, toluene, MeCN, alcohols). Poor water solubility expected.
  • Polarity: Moderately polar functional group (aldehyde) on a largely aliphatic ring; behaves well in medium-polarity aprotic media.
• Typical solvent choices by transformation (literature/practice)
  • Reductive amination: DCM or MeOH/EtOH/iPrOH with NaBH(OAc)3; MeCN or 2-MeTHF also used.
  • Imine/oxime formation: Toluene, benzene (Dean–Stark), or MeOH/EtOH with molecular sieves.
  • Organometallic additions (Grignard, RLi): Anhydrous Et2O or THF under inert atmosphere.
  • Wittig/Horner–Wadsworth–Emmons: THF, toluene, or DCM depending on ylide/phosphonate base.
  • Oxidation to acid: MeCN–water or acetone–water with oxidants (e.g., NaClO2 systems); or non-aqueous protocols for anhydrous oxidants.
• Quick comparison (selection tips)
  • DCM: Excellent for reductive amination and extractions; replace with EtOAc/2-MeTHF where greener choices are preferred.
  • THF/Et2O: Preferred for organometallics; consider 2-MeTHF as a greener alternative with similar performance.
  • Alcohols (MeOH/EtOH/iPrOH): Facilitate imine formation/reductive amination but may compete in acetal/hemiacetal equilibria.

Storage and Reconstitution

• Item-specific (Product Data)
  • Storage Conditions: Room temperature.
• General handling recommendations for aldehydes (literature/practice)
  • Store tightly sealed under inert atmosphere (N2/Ar) in amber glass to minimize oxidation to the corresponding acid; minimize headspace oxygen when practical.
  • Keep dry; use anhydrous techniques for moisture-sensitive transformations. Consider adding a molecular sieve packet to the container for extended storage (do not contact liquid directly during use).
  • If long-term storage is planned, refrigeration (2–8 °C) can further slow oxidation; allow to reach room temperature before opening to avoid moisture condensation.
  • Avoid repeated freeze–thaw cycles; dispense into small aliquots under inert gas for multi-use campaigns.
  • Reconstitution: Supplied neat (no reconstitution required). For stock solutions, prepare in dry solvent (e.g., DCM, THF, 2-MeTHF, MeCN) immediately before use. Verify concentration by weight or quantitative NMR if needed.
  • Stability checks: Monitor aldehydic proton (~9–10 ppm in 1H NMR) and IR C=O (~1720–1740 cm−1) to assess integrity over time.
  • Disposal: Treat as hazardous organic waste; follow institutional and local regulations.

Structure and Identity

• Item-specific (Product Data)
  • Product name: 4-Fluorocyclohexanecarbaldehyde (SKU: F978420)
  • CAS: 1554041-53-0
  • PubChem CID: 11297984
  • InChIKey: 264896 (as provided)
  • Storage condition: Room temperature
  • Research use: For research use only
• Literature/computed (reference information; not item-specific specs)
  • Preferred IUPAC name: 4-Fluorocyclohexane-1-carbaldehyde (positional isomer with F at para/4-position relative to CHO on the ring)
  • Molecular formula (calculated from structure): C7H11FO
  • Molecular weight (calc.): ~130.16 g/mol
  • Representative SMILES (one of several valid line notations): O=CC1CCC(F)CC1
  • Structural features: aliphatic six-membered carbocycle bearing an electron-withdrawing fluorine substituent at C4 and a formyl group at C1; no defined stereocenters in the parent structure; conformational isomers (chair flips) expected.
• 2D structural description (general)
  • A cyclohexane ring in a chair conformation with the aldehyde (–CHO) at the 1-position and a fluorine substituent at the 4-position. The –CHO carbon is sp2-hybridized and planar; the ring carbon bearing F is sp3-hybridized. The para relationship places F transannular to the formyl carbon, modulating inductive effects without strong resonance interactions.

Synthetic Utility

• Functional groups and reactivity
  • Electrophilic carbonyl (aldehyde) enables broad C–N and C–C bond formations. The ring-bound fluorine is inert under most conditions, preserving the fluorinated motif.
• Named/representative transformations (literature)
  • Reductive amination (Borate- or cyanoborohydride-based; catalytic hydrogenation) → secondary/tertiary amines with 4-fluorocyclohexylmethyl linkage.
  • Wittig and Horner–Wadsworth–Emmons olefinations → installation of vinyl groups while retaining the 4-F ring.
  • Organometallic additions (RMgX, RLi) → secondary carbinols; subsequent oxidation or substitution expands diversity.
  • Oxidation → 4-fluorocyclohexanecarboxylic acid or derivatives (amide formation, esterification) for bioisosteric exploration.
  • Oxime/hydrazone formation → intermediates for Beckmann-type rearrangements or as masked aldehydes.
  • Acetalization → temporary protection enabling base/nuceleophile-intensive steps.
• Retrosynthetic value
  • Positions the 4-fluorocyclohexyl fragment at an early stage, minimizing late-stage C–H fluorination challenges.
  • Provides a handle for convergent coupling: aldehyde couples with N-, O-, and C-nucleophiles under mild, chemoselective conditions.
• Practical notes
  • Electronic withdrawal by F slightly enhances aldehyde electrophilicity, often improving imine formation rates.
  • Avoid prolonged strong base to minimize self-condensation; protect as acetal if extensive basic chemistry is planned.

Target Specificity

• Not applicable. This product is a small-molecule aldehyde, not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
• For selectivity in chemical reactions, see Reaction & Applications and Synthetic Utility tabs.