3-Chloroadamantane-1-carboxamide - ≥95% , CAS No.6240-08-0

CAS: 6240-08-0 Cat. No.: C1354853 Formula: C₁₁H₁₆ClNO Molecular Weight: 213.71 PubChem CID: 4605931

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1C2CC3(CC1CC(C2)(C3)Cl)C(=O)N

IUPAC Name

3-chloroadamantane-1-carboxamide

InChIKey

FMXPGWNCORDLEA-UHFFFAOYSA-N

INCHI

1S/C11H16ClNO/c12-11-4-7-1-8(5-11)3-10(2-7,6-11)9(13)14/h7-8H,1-6H2,(H2,13,14)

Isomeric SMILES

C1C2CC3(CC1CC(C2)(C3)Cl)C(=O)N

PubChem CID

4605931

Molecular Weight

213.71

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Carboxylic acid derivatives
        • Level5 Carboxylic acid amides
          • Level6 Primary carboxylic acid amides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Carboxylic acid derivatives
• Intermediate Tree Nodes: Carboxylic acid amides
• Direct Parent: Primary carboxylic acid amides
• Alternative Parents: Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl chlorides
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Primary carboxylic acid amide - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Carbonyl group - Alkyl halide - Alkyl chloride - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as primary carboxylic acid amides. These are compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.
• 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

Chemical and Physical Properties

• Molecular Weight: 213.700 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 213.092 Da
• Monoisotopic Mass: 213.092 Da
• Topological Polar Surface Area: 43.100 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 288.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• 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 as a validated bioassay reagent. No WB/IHC/IF/FC or similar protocols are provided for this small-molecule building block.

Practical handling suggestions (general)

• Prepare stock solutions in dry DMSO or DMF (e.g., 10–100 mM) for screening or as reaction feedstocks; store aliquots tightly capped.
• For substitution reactions, see the Reaction Conditions tab for generic literature-style procedures.

For any assay or synthetic use, develop and validate protocols under your specific conditions.

Biological Roles

• Item-specific biological roles: Not applicable; no biological role is specified for this research chemical.

• General context (literature; not product-specific)

  • Adamantane is a rigid, lipophilic scaffold often used in chemical biology and materials science to modulate membrane association, hydrophobic packing, and steric profiles of ligands and probes.
  • Carboxamide functionality enables hydrogen bonding with protein backbones or side chains, potentially enhancing binding specificity in designed ligands; however, any such roles depend on the final derivative and target and are not intrinsic to this compound.
  • The tertiary chloride at C3 allows installation of diverse substituents (e.g., poly(ethylene glycol) fragments, azides for bioorthogonal labeling) to create tool compounds. These downstream constructs, not the starting material itself, may have defined biological interactions.

• Practical takeaway

  • Use this compound as a modular intermediate to craft adamantane-bearing probes or materials; verify biological compatibility/toxicity of the final constructs empirically.

All uses are restricted to research and laboratory applications; no clinical or diagnostic claims are made or implied.

Buffer Applications

This compound is a neutral, poorly water-soluble organic building block and is not typically used as a buffering agent or buffer component.

• Not applicable

  • No defined acid/base pair suitable for maintaining pH in aqueous solutions under laboratory buffer conditions.

• Practical note

  • If aqueous handling is required (e.g., for screening), prepare DMSO or DMF stock solutions and dilute into buffered media with attention to final cosolvent percentage and potential solvolysis of the tertiary chloride.

Green Alternatives

Greener choices primarily concern solvent systems and auxiliary reagents used with this building block. The substrate itself is a saturated hydrocarbon derivative with halogen content (Cl), so attention to waste minimization and reagent selection is key.

• Preferred solvent swaps (general guidance)

  • Replace DMF/NMP with MeCN, 2-MeTHF, or CPME where solubility and reactivity allow.
  • Favor ethanol or isopropanol for intentional solvolysis/etherification over methanol to reduce toxicity, acknowledging rate trade-offs.
  • Use EtOAc or Me-THF for extractions in place of dichloromethane where practicable.

• Reagent considerations

  • For halide substitutions, phase-transfer catalysis in MeCN or green ethers can reduce need for high-boiling dipolar aprotics.
  • Employ catalytic Lewis acids over stoichiometric silver salts to cut heavy-metal waste, when compatible with the nucleophile.

• Comparison (illustrative; not item-specific)

  Greener choice | Conventional | Trade-offs ---------------|-------------|----------- 2-MeTHF | THF/DCM | Slightly lower polarity; may need longer times MeCN | DMF/NMP | Easier removal; sometimes reduced solubility EtOAc | CH2Cl2 | Higher bp; may need warming for dissolution

• Waste and safety

  • Capture HCl byproduct with carbonate bases or scavengers to limit corrosive emissions.
  • Segregate halogenated waste streams; avoid unnecessary chlorinated solvent use.

Adopt solvent/reagent screening early to identify the greenest workable option for your transformation.

Pharmaceutical Uses

• Item-specific status: Not specified for pharmacopeial or formulation grade; intended for research use only.

• General information (no therapeutic claims)

  • Adamantane motifs are frequently incorporated into discovery-stage small molecules to enhance lipophilicity, membrane association, and metabolic stability. Carboxamides can modulate H-bonding and solubility.
  • 3-Chloroadamantane-1-carboxamide serves as a synthetic intermediate to access libraries of 3-substituted adamantane-1-carboxamides for structure–property studies relevant to excipient-likeness (e.g., hydrophobic modifiers) or as linkers to polymeric matrices.

• Formulation relevance (generic guidance)

  • Not commonly used as an excipient. If derivatized, adamantane-bearing compounds can act as hydrophobic anchors in nanoparticle or cyclodextrin-based systems (literature concept), but such applications pertain to downstream derivatives, not this starting material.

• Quality considerations

  • For any work intersecting regulated frameworks, obtain detailed impurity profiles and residual solvent data for the specific lot. In absence of such data here: “Not specified for this item; refer to CoA/Spec Sheet.”

This product is for research and laboratory use only.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/Literature guidance (non-spec; typical for adamantane carboxamides)

  • Physical state: typically crystalline solid for analogous adamantane-1-carboxamides; high lattice energy due to rigid cage (literature trend).
  • Solubility profile (qualitative):
    • Good in polar aprotic organics (DMSO, DMF, NMP); moderate in chlorinated solvents (CH2Cl2, CHCl3) and ethyl acetate.
    • Low in alkanes and water; amide increases polarity relative to hydrocarbon analogs.
  • Volatility: very low (high MW, non-flat polycycle, amide functionality) — suitable for weighing in open lab air.
  • Thermal behavior: adamantane derivatives often show sharp melting transitions; decomposition above mp is uncommon but avoid prolonged heating of tertiary chlorides to limit HCl-elimination or hydrolysis.
  • Partitioning: adamantane substituents impart high hydrophobic character; logP for adamantane amides commonly in the ~2–3.5 range (literature range; not item-specific).

• Not specified for this item; refer to CoA/Spec Sheet

  • Melting point, boiling point, density, refractive index, pKa, logP (measured), UV/Vis cutoff, water content, residual solvents, metal content.

Practical notes

• Prepare concentrated DMSO or DMF stock solutions for screening or reactions; warm gently (30–40 C) and sonicate if needed.
• Hygroscopicity is generally low, but the amide can hydrogen-bond with moisture; keep tightly capped to preserve consistency.

Quality and Grades

• Item-specific (from Product Data)

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

• Interpreting grades (general guidance)

  • Research/Chemical grade: suitable for synthesis and method development; impurity limits focus on assay purity and general contaminants.
  • HPLC/GC grade (if offered): emphasizes low UV background (HPLC) or low volatile residue (GC), useful when using the compound as a standard or in analytical workflows.
  • Pharma/USP/EP grade: tightly specified identity and impurity profiles for excipients or APIs (not implied for this product unless explicitly stated).

• Stabilizers/inhibitors

  • None specified for this item; refer to CoA/Spec Sheet. For tertiary chlorides, stabilizers are rarely used; stability is typically ensured by dry, neutral packaging.

• What to check on receipt

  • CoA assay (HPLC/GC): confirm purity and retention time match.
  • Identity: 1H/13C NMR of adamantane cage (characteristic upfield methine/methylene signals) and amide carbonyl in 13C (~170–175 ppm, literature), plus MS [M+H]+ ≈ 214.7.
  • Water and residual solvents: if critical to your process, request specific data; otherwise “Not specified for this item; refer to CoA/Spec Sheet.”

• Lot-to-lot control

  • For structure–reactivity studies (e.g., nucleophilic substitutions at C3), standardize solvent dryness and base content; tertiary chloride reactivity can be sensitive to trace water and acid/base impurities.

Reaction and Applications

3-Chloroadamantane-1-carboxamide is a dual-functional building block: a tertiary alkyl chloride (at C3) on a rigid adamantane cage and a C1 carboxamide. This combination enables orthogonal transformations.

• Substitution at C3 (tertiary chloride)

  • SN1-type substitutions: polar media promote formation of the 3-adamantyl cation; nucleophiles (ROH, RSH, H2O, N3−, halides) trap the cation to give 3-substituted adamantane-1-carboxamides.
  • Solvolysis/etherification: alcohols (MeOH, tBuOH) afford 3-alkoxy derivatives; rates increase with acidity/polarity.
  • Thioether and selenoether formation: soft nucleophiles (thiolates) efficiently capture the cation, furnishing robust C–S bonds.
  • Azidation/amination: NaN3 (DMF/MeCN) gives 3-azido analogs, which can be reduced or used in click chemistry.

• Transformations at C1 (amide handle)

  • N-acylation to imides/ureas: via activation (e.g., CDI, triphosgene) to isocyanate-like intermediates under controlled conditions.
  • Hydrolysis to acid: acidic or basic conditions convert the amide to the corresponding adamantane-1-carboxylic acid, enabling esterification or amide re-coupling (literature; requires forcing conditions due to amide stability).
  • Cross-coupling not applicable directly; however, introducing other leaving groups at C3 (e.g., via halide exchange) can extend diversification.

• Use cases (research context)

  • Scaffold diversification in materials/medchem: installing polar heads at C3 while retaining the amide H-bonding motif at C1.
  • Ligand design: adamantane provides steric bulk and lipophilicity; the amide tunes H-bonding and solubility.

Tips

• Control moisture and acid/base content to steer between solvolysis vs substitution pathways.
• Silver salts (AgBF4/AgNO3) or Lewis acids can accelerate ionization of tertiary chlorides (literature practice) if needed.

Reaction Conditions

General literature-guided conditions for transforming 3-chloroadamantyl systems and adamantane carboxamides. Adjust for your substrate and scale; these are non-item-specific guidelines.

• Nucleophilic substitution at C3 (SN1-dominant)

  • Solvents: MeCN, nitromethane, HFIP, or DMF to enhance ionization; avoid excess water unless hydrolysis is intended.
  • Nucleophiles: ROH (1.5–5 equiv), RSH (1.2–2 equiv as thiolate), NaN3 (1.5–2 equiv), secondary amines (2–3 equiv) with base.
  • Additives: catalytic Ag+ (AgBF4/AgNO3, 5–10 mol%) or Lewis acids (BF3·OEt2) can accelerate ionization; bases (K2CO3, Hunig’s base) to neutralize HCl.
  • Temperature/time: 0–80 C, 1–24 h depending on nucleophile strength and solvent polarity.

• Azidation example (literature-style)

  • 1.0 equiv substrate in dry DMF (0.1–0.3 M), 1.5 equiv NaN3, 50–70 C, 4–12 h; work up with water and extract with EtOAc.

• Alcohol solvolysis (to 3-alkoxy)

  • Substrate (0.05–0.2 M) in ROH/MeCN (1:1), 2–3 equiv ROH total, 25–60 C, 3–16 h; optional AgNO3 (5 mol%) to boost rate.

• Manipulation of the C1 amide

  • Hydrolysis to acid: reflux in 6 M HCl or 2–4 M NaOH with co-solvent (dioxane/MeOH) for extended times (12–48 h); then re-derive as needed (literature practice; amide hydrolysis is typically forcing).
  • Couplings (from acid): EDCI/HOBt, HATU, or DIC/DMAP in DMF or DCM, 0–25 C, 1–16 h.

• Workup/purification

  • Neutralize acid/base carefully; silica gel chromatography with hexanes/EtOAc or DCM/MeOH mixes.

Always confirm reaction progress by NMR/LC–MS; tertiary carbocation pathways can yield rearrangements/minor byproducts in some systems.

Safety and Handling

• Item-specific (from Product Data)

  • GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
  • Storage: Room temperature. Ship: Normal.

• General safety guidance (literature-based; not a substitute for SDS)

  • Likely hazards: organic amides are commonly of low to moderate toxicity; tertiary alkyl chlorides can be irritants and may generate HCl upon hydrolysis. Avoid inhalation of dust and contact with skin/eyes.
  • PPE: lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile). Weigh in a fume hood to minimize dust exposure.
  • Incompatibilities: strong bases (risk of amide deprotonation and elimination/substitution at C–Cl under forcing conditions), strong acids (accelerate solvolysis to alcohols), and strong nucleophiles (azide, thiolates) if substitution is not intended.
  • Handling tips: keep containers tightly closed; use dry utensils/solvents to avoid unintended hydrolysis or substitution at the tertiary chloride.
  • First aid (overview):
    • Inhalation: move to fresh air; seek medical attention if symptoms persist.
    • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; get medical advice if irritation continues.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Stability considerations

  • Tertiary adamantyl chlorides undergo SN1-type solvolysis in strongly polar protic media; maintain neutral, dry conditions for storage to maximize shelf life.

Always consult the product SDS for authoritative hazard and response information.

Solvent Selection

This compound is a hydrophobic, rigid adamantane derivative with one polar amide. Solvent choice is driven by the desired balance between dissolving the amide and controlling the reactivity of the tertiary chloride.

• Polarity and miscibility (general trends)

  • Polar aprotics (DMSO, DMF, NMP): highest solvating power for the amide; excellent for stock solutions and SN1/SN2 reactions with ionic nucleophiles.
  • Moderately polar solvents (MeCN, acetone, EtOAc, CH2Cl2, CHCl3): good solubility with better volatility and easier workup.
  • Protic solvents (MeOH, EtOH, iPrOH): increase propensity for solvolysis (alkoxy substitution) — useful if intentional, avoid if stability is critical.
  • Aqueous media: very limited solubility; use cosolvents (≤5–10% DMSO/DMF) if needed.

• Practical selection tips

  • For nucleophilic substitutions at C3: use MeCN, nitromethane, or DMF with the nucleophile; add mild base to neutralize HCl formed; keep water low.
  • For amide coupling/derivatization at C1 (via acid or activated intermediates): use DMF, DCM, or THF under standard peptide coupling conditions after converting the amide to the corresponding acid (if applicable) or by using activating agents.
  • For analytics: DMSO-d6 or CDCl3 are typical NMR solvents; amide NH may show solvent-dependent exchange.

• Quick comparison

  • DMSO vs MeCN: DMSO maximizes solubility but is harder to remove; MeCN balances solubility with ease of evaporation and lower background for MS/LC.

Storage and Reconstitution

• Item-specific (from Product Data)

  • Storage conditions: Room temperature.
  • Shipped: Normal.

• General storage guidance (supporting)

  • Keep tightly closed in a dry, inert atmosphere (optional desiccant) to minimize moisture-driven solvolysis of the tertiary chloride.
  • Store away from strong acids/bases and strong nucleophiles. Ambient light is generally acceptable; avoid prolonged UV exposure to limit radical processes.

• Reconstitution and stock solutions

  • Solvents: DMSO, DMF, MeCN, CH2Cl2, or EtOAc. Begin with 10–20 mg/mL; warm gently (30–40 C) and sonicate if needed.
  • Aqueous use: dilute organic stock into buffer with vigorous mixing; keep final DMSO/DMF ≤1–5% v/v as required by your system. Be aware that protic media can drive solvolysis at C3.
  • Filtration: if particulates remain, pass through 0.22 μm PTFE filter.

• Stability after reconstitution (general)

  • Organic solutions are typically stable for days at room temperature and weeks at 2–8 C under dry, neutral conditions. For longest life, store aliquots under inert gas at 2–8 C.
  • Monitor for signs of substitution (e.g., formation of alcohol adducts) if stored in protic solvents.

• Specifications not provided

  • Exact shelf life, retest period, and solution stability: Not specified for this item; refer to CoA/Spec Sheet.

Always consult the SDS and CoA for definitive storage and handling instructions.

Structure and Identity

A rigid, polycyclic adamantane scaffold bearing a carboxamide at bridgehead C1 and a chloro substituent at C3. The framework is a diamondoid tricyclo[3.3.1.1^3,7]decane core, conferring high steric bulk and hydrophobicity.

• Item-specific (from Product Data)

  • SKU: C1354853
  • Product name: 3-Chloroadamantane-1-carboxamide
  • CAS: 6240-08-0
  • InChIKey: 86887 (as provided)
  • Storage conditions: Room temperature; shipped normal
  • Research use: For research use only

• Computed/Literature (non-spec; for reference only)

  • Molecular formula (derived from structure): C11H16ClNO
  • Molecular weight (calculated): ~213.70 g/mol
  • Core features: adamantane cage; functional groups: one secondary amide (–CONH2) at C1; one tertiary alkyl chloride at C3.
  • 2D description: a tricyclic adamantane skeleton with the amide carbonyl and –NH2 projecting from a bridgehead carbon; chloride on a tertiary carbon two atoms away across the cage.

• Not specified for this item; refer to CoA/Spec Sheet

  • SMILES
  • Full standard InChI and validated InChIKey

Notes

• The tertiary C–Cl on adamantane is predisposed to ionization (3-adamantyl cation character), enabling substitution chemistry under SN1-type conditions.
• The amide at C1 is non-basic and can engage in H-bonding as a donor/acceptor, modestly increasing polarity relative to unsubstituted adamantyl chlorides.

Synthetic Utility

The molecule’s orthogonal handles enable efficient diversification on a rigid, lipophilic scaffold.

• C3 tertiary chloride: gateway to rapid cation-capture chemistry

  • SN1 substitutions with O-, N-, S-, and N3− nucleophiles in polar media produce 3-substituted derivatives with high steric definition.
  • Halide exchange (e.g., to iodide) can be achieved under Finkelstein-like conditions in polar aprotics if needed for rate enhancement (literature-dependent).
  • Formation of C–C bonds via stabilized carbocation trapping by electron-rich arenes (Friedel–Crafts-type, Lewis acid assisted) is feasible on adamantyl systems.

• C1 carboxamide: platform for further functional interconversions

  • Hydrolysis to the corresponding acid enables classical esterification and amide coupling to introduce diverse N-substituents.
  • N-acylation/urea formation via activation (e.g., CDI) expands H-bonding arrays without disturbing the adamantyl core.
  • Late-stage isotopic labeling at the amide (15N) or carbonyl (13C) can be implemented through exchange or re-synthesis for mechanistic studies.

• Strategic roles in synthesis

  • Scaffold rigidification: projects substituents into well-defined 3D space, valuable in SAR and materials design.
  • Protecting-group-like behavior: the amide can be retained as a polarity handle during C3 diversification, then transformed to other carbonyl derivatives.

• Purification/analysis tips

  • Substituted adamantane amides generally chromatograph well on silica (hexanes/EtOAc or DCM/MeOH gradients). Monitor by TLC (UV weak; use staining) and LC–MS ([M+H]+ ≈ 214.7 for parent).

Target Specificity

Not applicable. This product is a small-molecule research chemical, not a biological macromolecule or antibody. No target, epitope, clone, isotype, or species reactivity information is associated with this item.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 6240-08-0, the molecular formula is C11H16ClNO, and the molecular weight is 213.71 g/mol. InChIKey FMXPGWNCORDLEA-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.