≥95%(GC), contains 0.2 % CaCO3/MgO (1:2) as stabilizer for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
개요
application：
2-Chlorocyclohexanone, is an intermediate in the synthesis of variety of pharmaceutical compounds. It is also an intermediate in the synthesis of 1-Chloro-2-methylenecyclohexane .
This compound belongs to the class of organic compounds known as alpha-chloroketones. These are organic compounds contaning a chlorine atom attached to the alpha carbon atom relative to C=O group.
External Descriptors
Not available
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.
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Application Protocols
Not applicable.
No immunoassay or bioanalytical application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic procedures, see the Reaction Conditions and Synthetic Utility sections.
Biological Roles
Applicability
This product is a synthetic organic building block and is not intended for biological use in living systems.
General biochemical perspective (literature/general)
α-Haloketones are reactive electrophiles capable of alkylating nucleophilic residues (e.g., cysteine, lysine) in proteins under forcing conditions. This reactivity underpins their use as enzyme probes in mechanistic studies but also contributes to irritancy and potential cytotoxicity in vitro.
No known endogenous role: 2-chlorocyclohexanone is not a natural metabolite or cofactor. Any biological interactions are nonspecific and driven by electrophilicity rather than target selectivity.
Practical note
If used in biochemical experiments, treat strictly as a reactive chemical probe; rigorously control concentration, exposure time, and quench conditions. All work is for research use only, not for diagnostic or therapeutic applications.
Buffer Applications
Not typically applicable.
2-Chlorocyclohexanone is a neutral organic reagent and is not used to prepare laboratory buffers or as a buffering component.
For aqueous work, select a compatible buffer based on the intended reaction (e.g., carbonate for Favorskii in water-rich media), but the compound itself does not contribute buffering capacity.
Green Alternatives
Context
2-Chlorocyclohexanone is a halogenated electrophile; while highly useful, it carries inherent environmental and safety considerations (halide waste, potential lachrymatory properties). Greener strategies can sometimes replace either the reagent or the conditions under which it is used.
Greener synthetic strategies (literature/general)
Direct α-functionalization of cyclohexanone: Organocatalytic or photoredox C–H activation (e.g., enamine catalysis with nitrosocarbonyls, hypervalent iodine-mediated α-oxyamination/α-oxygenation) can obviate pre-halogenation, reducing halogenated waste.
Elimination alternative: If the target is cyclohex-2-enone, catalytic dehydrogenation or TEMPO/hypoiodite-free oxidation methods may avoid halide usage.
Nucleophilic substitution endpoints: For introducing amines or thiols at the α-position, oxidative α-aminations/thiolations (electrochemical or iodine(III)-mediated) can be explored to minimize chlorinated byproducts.
Greener media and operations
Solvent choice: Prefer 2-MeTHF, CPME, EtOAc, or MeCN over DMF/DMSO/NMP when feasible (balance kinetics vs EHS). Employ water/EtOH for Favorskii captures when compatible.
Base selection: Carbonate bases and organic superbases with lower EHS footprints (DBU in green ether solvents) may replace strong inorganic bases in some cases.
Process intensification: Flow chemistry for halogenation/substitution steps reduces inventory of reactive intermediates and improves heat/mass transfer.
Trade-offs
Rate/selectivity may be lower without the α-chloro handle; additional steps or catalysts can offset green benefits. Pilot experiments and life-cycle assessments are recommended.
Pharmaceutical Uses
Scope
No excipient or formulation role is anticipated for 2-chlorocyclohexanone.
Process chemistry context (literature/general)
It may be employed as a synthetic intermediate in the preparation of cyclic enones, ring-contracted carboxylates (via Favorskii), or α-substituted cyclohexanone scaffolds that can feed into active pharmaceutical ingredient (API) syntheses.
Benefits: Convergent installation of α-heteroatoms enables downstream diversification; the possibility of ring contraction offers access to cyclopentane-containing motifs prevalent in medicinal chemistry.
Considerations: Residual chloride and byproduct halides must meet ICH Q3A/Q3D impurity and elemental impurity expectations in GMP settings. Robust purge strategies (crystallization, phase separations, scavengers) are recommended.
Regulatory note
This product is offered for research and laboratory synthesis only. It is not a drug, nor is it intended for diagnostic, therapeutic, or human/animal consumption uses.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for reference only; not item specifications)
Physical state: Typically a colorless to pale-yellow liquid for many α-haloketones of this ring size (literature generalization).
Density, refractive index, melting/boiling points, UV cutoff, water/peroxide/metal content: Not specified for this item; consult SDS/CoA or primary literature.
Solubility (qualitative, literature): Expected to be miscible with common organic solvents such as dichloromethane, chloroform, acetone, ethyl acetate, and ethers; low solubility in water typical for cyclohexanone derivatives.
pKa/logP (literature trends): The α-C–H acidity is enhanced vs cyclohexanone due to the α-chloro substituent; exact pKa and logP values are not specified here.
General notes for users
α-Haloketones can undergo slow dehydrohalogenation; distilled material may show evolution of HCl on prolonged heating. For precise physical constants (bp, mp, density, nD), use lot-specific CoA or measure under your lab conditions.
Quality and Grades
Item-specific quality details
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and any stabilizers.
General guidance on quality for α-haloketones (literature/practice)
Assay considerations: Purity can be monitored by GC or 1H NMR; typical degradants include cyclohexenone (via elimination) and dihalogenated/byproduct species from synthesis.
Stabilizers: α-Haloketones are sometimes shipped without stabilizers; if any inhibitor/stabilizer is present, it will be declared on the CoA. Absence of stabilizer increases the importance of cold, dark storage.
Water and acid content: Trace HCl or moisture can accumulate; Karl Fischer and acid number titrations are useful if process-critical. Item-specific numeric limits are not provided here.
UV background: If using in photochemical steps or as an HPLC analyte, check UV cutoff empirically; low-UV grades are not specified for this listing.
What the grade implies (general)
"Analytical Reagent/HPLC" grades emphasize low nonvolatile residue and low UV absorbance; "Synthesis" or "Technical" grades emphasize assay with broader impurity specs. Since this listing does not state grade, select and qualify material based on your application (e.g., medicinal chemistry vs bulk process) and verify against the CoA.
Reaction and Applications
General roles of 2-chlorocyclohexanone (literature; expand-on-use)
Electrophilic α-haloketone: The α-chloro substituent activates the adjacent carbon toward nucleophilic substitution, enabling rapid access to 2-substituted cyclohexanones (C–N, C–O, C–S, C–C bond formation).
Favorskii rearrangement: Under basic conditions, α-haloketones undergo Favorskii to afford ring-contracted carboxylic acids/esters. 2-Chlorocyclohexanone can furnish cyclopentanecarboxylate derivatives upon capture by nucleophiles (ROH, H2O, amines).
Elimination to enone: Strong base promotes dehydrohalogenation to cyclohex-2-enone (enone), a versatile Michael acceptor and Diels–Alder dienophile.
α-Functionalization platform: Displacement with azide, cyanide, thiolates, or alkoxides yields α-azido, α-cyano, α-thio, or α-alkoxy ketones, respectively. These intermediates participate in further rearrangements (e.g., Curtius from acyl azides via subsequent transformations) or reductions.
Stereocontrol: Nucleophilic substitution at the α-position can be stereoselective from a chair conformation; choice of solvent/base and temperature influences axial/equatorial approach and product configuration where relevant.
Building block in total synthesis: Serves as a masked enone/β-keto functionality; strategic for ring contraction sequences and for installing α-heteroatom substituents used downstream in reductive or radical manipulations.
Practical notes
Competing pathways (SN2 vs E2 vs rearrangement) are solvent- and base-dependent; milder nucleophiles (e.g., thiolates) in polar aprotic media favor substitution, while strong, non-nucleophilic bases favor elimination.
Workup often benefits from acid quench to neutralize residual base and suppress retro-elimination; monitor by GC/LC to distinguish cyclohexenone byproduct.
Reaction Conditions
General guidance from literature (illustrative; adjust to your system)
Nucleophilic substitution (amines): 2–5 equiv amine, 0.5–1.0 equiv base (Et3N or Na2CO3), solvent MeCN or THF, 0–25°C, 1–12 h. Monitor by TLC/GC. For secondary amines, use MeCN and mild heating (40–60°C) if needed.
Thiolate substitution: NaS-R (1.2–1.5 equiv) in DMF or DMSO, 0–25°C, 0.5–4 h. Quench with dilute acid to suppress elimination.
Alkoxylation: Sodium alkoxide (1.2–2.0 equiv) in the corresponding alcohol or in THF/ROH mixed solvent, 0–25°C; limit base strength/time to minimize enone formation.
Cyanation: NaCN or KCN (caution, toxic) in polar aprotic solvent/water biphasic with phase-transfer catalyst; 0–25°C, 1–3 h.
Favorskii rearrangement: Aqueous NaOH (1–3 M) or RO- /ROH (alkoxide/alcohol), 0–25°C, 1–6 h; products are ring-contracted acids/esters. Temperature elevation can accelerate but may broaden product distribution.
Elimination to cyclohexenone: t-BuOK (1.1–1.5 equiv) in THF or t-BuOH, 0–25°C, 0.5–2 h; or DBU (1.2–2 equiv) in toluene/THF at ambient to 60°C.
Operational considerations
Dry, oxygen-free conditions reduce side reactions. Add reagent last to solutions of nucleophile/base when possible.
Analytical control: GC or HPLC with rapid sampling differentiates SN2 (heavier product) from E2 (lighter enone). 1H NMR diagnostic: vinylic signals (~6–7 ppm) indicate enone formation.
Disclaimer
Conditions above are literature-style guidance and not item-specific manufacturing instructions. Optimize for your substrate/nucleophile and scale.
Safety and Handling
Item-specific hazard information
GHS classification, signal word, H-statements, and pictograms: Not specified for this item; refer to the product SDS for authoritative safety information.
General safety considerations for α-haloketones (literature/experience)
Hazard profile: α-Haloketones are typically strong electrophiles, irritant to skin/eyes/respiratory tract, and may be sensitizers or lachrymators. They can alkylate nucleophiles (e.g., amines, thiols).
PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles; handle in a fume hood.
Incompatibilities: Strong bases (risk of rapid dehydrohalogenation/Favorskii chemistry and heat), strong nucleophiles (uncontrolled substitution), strong oxidants or reducing agents; avoid contact with amines in confined spaces (possible exotherm/lachrymation).
Handling tips: Work under inert atmosphere when high purity is required to minimize hydrolysis and HCl formation. Keep containers tightly closed to limit adventitious moisture.
First aid (overview; defer to SDS): In case of skin/eye contact, rinse with copious water for ≥15 minutes and seek medical attention. If inhaled, move to fresh air. If ingested, do not induce vomiting; seek medical attention.
Spill/response: Absorb with inert material, avoid bases during cleanup to minimize corrosive HCl evolution; ventilate area.
Waste: Collect halogenated organic waste per institutional and regulatory guidelines.
Note: Always consult the specific SDS supplied with the lot for definitive hazard classifications and response procedures.
Solvent Selection
Applicability
This product is itself an organic reagent/solute rather than a general-purpose solvent. However, effective solvent choice is critical for its storage and for reactions where it serves as an electrophile.
Polarity/miscibility profile (literature/general)
Polarity class: Moderately polar aprotic (ketone functionality) with added lipophilicity from the cyclohexyl ring and a chloro substituent.
Expected miscibility: Good solubility in dichloromethane, chloroform, acetone, ethyl acetate, THF, and ethers; limited solubility in hexanes and water.
Choosing reaction media (examples, literature)
Nucleophilic substitutions (e.g., amines/thiolates): Polar aprotic solvents (DMF, DMSO, MeCN, NMP, or THF) to enhance SN2 rates; control base strength to mitigate elimination.
Favorskii rearrangement: Alcoholic solvents (MeOH, EtOH) or aqueous media with base; product capture as ester or acid depending on nucleophile.
Dehydrohalogenation to cyclohexenone: Nonprotic, hindered bases in THF, toluene, or DMSO; temperature control recommended.
Enolate chemistry/umpolung variants: Use of LDA or NaHMDS in THF at low temperature when halide is a spectator or leaving group management is desired.
Practical tips
Avoid highly basic solvent systems during storage. For scale-up SN2, DMF/MeCN offer kinetics, whereas THF/EtOAc may simplify workup.
If chromatography is anticipated, DCM/EtOAc systems often give good mobility; monitor for partial elimination to cyclohexenone on silica.
Storage and Reconstitution
Item-specific instructions (from Product Data)
Storage conditions: Store at -20°C.
Shipping: Ice chest with ice pads.
General handling guidance (literature/practice)
Container: Store in tightly sealed amber glass to minimize light- and moisture-induced degradation; consider nitrogen/argon headspace for long-term storage.
Freeze–thaw: Minimize repeated freeze–thaw cycles. If aliquoting is feasible, divide into small volumes upon receipt.
Warming before use: Allow the container to equilibrate to room temperature in a closed state to prevent water condensation inside. Mix gently before dispensing.
Stability notes: α-Haloketones can slowly eliminate HCl to form enones under basic or warm conditions. Keep cold and avoid prolonged exposure to bases. If discoloration or HCl odor develops, analyze by GC/NMR before critical use.
Reconstitution
Not applicable; supplied neat as an organic reagent (appearance and concentration not specified for this item; refer to CoA/Spec Sheet). If dilution is required for dosing or storage, use dry, compatible solvents such as DCM, THF, or MeCN and store cold.
Structure and Identity
Item-specific (from Product Data)
SKU: C103549
Product name: 2-Chlorocyclohexanone
CAS: 822-87-7
PubChem CID: 13203
InChIKey: 40453 (as provided)
Storage: Store at -20°C
Shipping: Ice chest + ice pads
Literature/computed identity (general reference; not item-specific specs)
Structural features (general chemistry description)
Ring system: Saturated six-membered carbocycle (cyclohexanone) bearing a carbonyl at C1.
Functional groups: Secondary ketone (cyclohexanone), α-chloro substituent at C2 (α-haloketone).
Electrophilic centers: Carbonyl carbon (C=O) and the α-carbon bearing chlorine (activated toward SN2/SN1′-type substitution and base-promoted rearrangements/eliminations).
2D description: A chair-like cyclohexanone ring; chlorine is attached to the carbon adjacent (α) to the carbonyl. No stereocenter when planar enolization is rapid; however, transient configurational isomers can be observed in substitution reactions on the α-carbon.
Note: Exact structural identifiers for this item should be verified against the Certificate of Analysis (CoA) if required for regulatory or analytical purposes.
Synthetic Utility
Key functional elements
α-Halo activation: The C–Cl bond adjacent to the carbonyl makes the α-carbon a versatile leaving site, unlocking SN2 substitutions and base-mediated rearrangements.
Carbonyl reactivity: The ketone remains available for enolate formation, additions, condensations, and reductions, enabling orthogonal transformations.
Favorskii rearrangement: Base (NaOH, KOH, alkoxide) converts 2-chlorocyclohexanone into ring-contracted carboxylates; trapping with ROH affords esters.
Elimination: Strong base (t-BuOK, DBU) gives cyclohex-2-enone.
Tandem sequences: Displacement → reduction (e.g., NaBH4, catalytic hydrogenation), or substitution → intramolecular cyclization to assemble bicyclic systems.
Cross-coupling after activation: Conversion to the corresponding α-boronic ester or α-stannane via halogen–metal exchange (under carefully controlled conditions) can enable C–C bond formation.
Retrosynthetic value
Serves as a linchpin for installing α-heteroatoms or for accessing cyclopentane carboxylate motifs by ring contraction, thus bridging six-membered to five-membered frameworks commonly found in bioactive targets.
Practical tips
Control basicity/nucleophilicity to steer SN2 vs E2 vs Favorskii. Use low temperatures for enolate chemistry; monitor for enone formation during workup/purification.
Target Specificity
Not applicable.
This product is a small-molecule building block, not a biological macromolecule or affinity reagent. It does not have antigen/epitope, clone, isotype, or species reactivity attributes.
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