6,8-dichlorooctanoic Acid - ≥97% , CAS No.41443-60-1

CAS: 41443-60-1 Cat. No.: D997349 Formula: C₈H₁₄Cl₂O₂ Peso molecolare: 213.1 PubChem CID: 9964447

QUALITÀ & PUREZZA ≥97%

Storage

Room temperature

Specifiche

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

Sorrisi canonici

C(CCC(=O)O)CC(CCCl)Cl

IUPAC Name

6,8-dichlorooctanoic acid

InChIKey

HSKAEXWPLIDFGC-UHFFFAOYSA-N

INCHI

1S/C8H14Cl2O2/c9-6-5-7(10)3-1-2-4-8(11)12/h7H,1-6H2,(H,11,12)

Isomeri SMILES

C(CCC(=O)O)CC(CCCl)Cl

PubChem CID

9964447

Peso molecolare

213.1

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Medium-chain fatty acids
• Alternative Parents: Halogenated fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Medium-chain fatty acid - Halogenated fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Carbonyl group - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
• 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: 213.100 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 212.037 Da
• Monoisotopic Mass: 212.037 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 128.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 predefined biological assay protocols or analytical application methods are specified for this item. Usage is highly project-dependent (e.g., synthetic transformations, derivatization workflows).

General laboratory guidance:

• Prepare stock solutions in suitable organic solvents (e.g., DCM, THF, MeOH, MeCN) based on the intended reaction.
• For aqueous or biochemical contexts, first derivatize (e.g., to a salt or ester) or dissolve in a miscible co-solvent; perform solvent controls.
• Validate reaction conditions at small scale, monitor by TLC/GC/HPLC, and characterize products by NMR and MS.

Refer to your method SOPs or primary literature for task-specific protocols.

Biological Roles

Item-specific note: This product is supplied for research use only.

General/literature context (no clinical claims):

• Structural class: Medium-chain fatty acid (C8) analogue bearing halogens. Halogenation increases hydrophobicity and can alter interactions with lipid bilayers and proteins relative to native octanoic acid.
• Metabolic considerations: Carboxylic acids of this chain length are typically activated to acyl-CoA thioesters and enter β-oxidation; however, halogenation at internal/terminal carbons may impede or redirect enzymatic processing in vitro. Such analogs are often explored as chemical probes to study fatty acid transport, activation, or membrane association in biochemical systems.
• Binding/partitioning: Elevated logP may enhance association with membranes, micelles, and serum albumin compared to non-halogenated C8 acids, influencing observed activities in biochemical assays.
• Reactivity as a probe: The terminal (C8) chloride enables post-incubation derivatization (e.g., conversion to azide/alkyne handles) for click-based tagging of modified biomolecules in chemical biology workflows, following prior synthetic derivatization to ensure biocompatibility.

Caveats:

• Enzyme inhibition/activation profiles are highly system-dependent; consult primary literature for study-specific observations.
• Avoid extrapolation to physiological or therapeutic effects; design experiments with appropriate in vitro controls and concentrations, and verify purity and counter-ion content.

Buffer Applications

This compound is a hydrophobic carboxylic acid and is not typically used as a buffering agent. In aqueous systems, its limited water solubility (in the protonated form) and lack of a suitable conjugate acid/base pair near neutrality limit its utility as a buffer.

Practical notes:

• If incorporation into aqueous media is required (e.g., for biochemical assays), dissolve first in a water-miscible cosolvent (MeOH, EtOH, DMSO) or prepare a stock of its sodium/potassium carboxylate by neutralization with NaOH/KOH to enhance solubility.
• Select established buffers (e.g., phosphate, Tris, HEPES) for pH control; use this acid only as a solute or as part of a substrate mixture, not for buffering.

Green Alternatives

While the substrate itself is a halogenated fatty acid, greener practices can be implemented primarily through solvent and reagent choices.

Greener solvent substitutions (general guidance):

• Replace DCM/chloroform with 2-MeTHF, CPME, or EtOAc when feasible (comparable solvency for carboxylic acids and many nucleophiles).
• Favor MeCN, ethyl acetate, or propylene carbonate in place of DMF/DMSO where kinetics permit.
• Use toluene or bio-based solvents (e.g., Cyrene) for esterifications and couplings when validated.

Reagent considerations:

• Amide couplings: Employ coupling reagents with improved hazard profiles (e.g., T3P in EtOAc) and minimize stoichiometric carbodiimides. Solid-supported scavengers can simplify workup.
• Halide activation: Use catalytic halide exchange (NaI in acetone) instead of harsh reagents to activate secondary chloride.
• Base selection: Prefer carbonate/bicarbonate bases to limit EHS risks when SN2 at the primary chloride is sufficient.

Illustrative comparison (general):

• Conventional: DCM (excellent solubility), DMF (SN2), DCC/DMAP (esterification).
• Greener alternative: 2-MeTHF or EtOAc (workup-friendly, lower toxicity), MeCN (polar aprotic with better EHS), T3P/EtOAc or catalytic HCl/ROH for esterification.

Trade-offs:

• Polar aprotic green alternatives may reduce SN2 rates; compensate with modest temperature increases, higher nucleophile loading, or PTC catalysts.
• 2-MeTHF/CPME can hold more water; include drying (molecular sieves) for moisture-sensitive steps.

Pharmaceutical Uses

No pharmacopeial/excipient status is specified for this item; refer to CoA/Spec Sheet.

Formulation and process chemistry context (general):

• Role as an intermediate: Halogenated fatty acid derivatives can serve as building blocks in the synthesis of lipid-like excipients, pro-moieties, or surface-modifying agents. The carboxyl group allows conjugation to amines/ols (amide/ester formation), and the terminal chloride facilitates further functionalization.
• Salt forms: Conversion to sodium/potassium salts increases aqueous solubility and may aid in processing, but any pharmaceutical application would require dedicated safety and regulatory evaluation.
• Analytical considerations: For process development, monitor for dehalogenation or elimination impurities; use RP-HPLC with an acidified mobile phase for robust quantitation of carboxylates.

Compliance note:

• This product is offered strictly for research and laboratory use. It is not approved for human or veterinary use, diagnostic procedures, or as an active pharmaceutical ingredient or excipient without appropriate qualification.

Physical Properties

Item-specific specifications:

• Appearance: 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.
• Density, BP, MP, refractive index, water/peroxide/metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed properties (general guidance, not specifications):

• Approximate formula and FW (literature): C8H14Cl2O2, FW ~213.10 g/mol.
• Phase/volatility: Expected to be a low-volatility liquid or low-melting solid; carboxylic acids of C8 length are often liquids near ambient temperature; dichloro substitution can raise boiling point and density (literature trend for halogenated fatty acids).
• Acidity: Carboxylic acids typically show pKa ~2–5. Electron-withdrawing chlorines generally increase acidity relative to octanoic acid (pKa 4.89), but a specific, peer-reviewed pKa for 6,8-dichloro analog is not widely cited.
• Solubility profile (qualitative, literature): Poorly soluble in water in the protonated form; soluble/miscible in chlorinated solvents (e.g., DCM, chloroform), good solubility in ethers (THF), esters (EtOAc), and polar protic solvents (MeOH, EtOH). Readily soluble in aqueous base as the carboxylate salt.
• Partitioning: Medium-chain, halogenated acids generally exhibit elevated logP relative to the parent acid; specific logP for this compound is not broadly cataloged.

General chemistry notes:

• The presence of a primary and a secondary C–Cl bond suggests distinct reactivity/solvolysis tendencies, which may subtly influence measured physical properties (e.g., refractive index and density).

Quality and Grades

Item-specific quality 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.

Guidance on grades and implications (general):

• Research grade/chemical grade: Suitable for most synthetic and materials research. Trace impurities (water, residual solvents, or inorganic salts) can influence moisture-sensitive couplings (e.g., acid chloride formation) or nucleophilic substitutions at the alkyl chloride sites.
• Low-UV/HPLC grade (if offered for similar acids): Tailored for chromatographic applications with minimized UV-active impurities and particulates; useful when quantifying reaction conversions by HPLC/UV.
• Acidic halide content: For halogenated fatty acids, residual halides or over-chlorinated congeners can co-elute; CoA typically provides purity by GC/HPLC and may include residual solvent analysis.
• Verification: For this structure, 1H/13C NMR and HRMS are informative; 35Cl/37Cl isotopic patterns assist in confirming dichloro substitution. Titrimetric acid value and GC purity help assess lot-to-lot consistency.

Recommendations:

• Check the CoA for exact purity assay, water content, and residual solvents for your lot.
• If using in stereospecific transformations at C6 (upon substitution), monitor for racemization or elimination by-products.
• For analytical work, consider pre-drying under vacuum and verifying acid value prior to use.

Reaction and Applications

Chemotype-driven applications:

• Bifunctional handle: Combines a carboxylic acid with two alkyl chlorides (primary at C8, secondary at C6), enabling orthogonal transformations.

Representative transformations (literature/general):

• Amide/ester formation: Standard peptide-type couplings (HATU/HBTU/EDC/DIC with bases such as DIPEA or collidine) to form amides; Fischer or Steglich esterification (DCC/DMAP) to prepare esters for protecting or derivatization.
• SN2 at C8 (primary C–Cl): Installation of azide (NaN3 → subsequent Staudinger or reduction to amine), thiolates (R–S−), cyanide (KCN; caution), or alkoxides to access a library of ω-functionalized octanoates.
• Substitution at C6 (secondary C–Cl): Requires stronger nucleophiles or catalytic activation (e.g., iodide exchange, phase-transfer, or metal-catalyzed substitution). Competing E2 elimination can form internal alkenes; controlling base strength and temperature is key.
• Intramolecular cyclizations: After nucleophile installation, lactonization or macrolactamization can be pursued via the acid group, offering access to medium-ring motifs.
• Reductive strategies: Selective dehalogenation (e.g., Raney Ni, Zn/AcOH) can tune substitution patterns; convert –CO2H to acid chloride (SOCl2, oxalyl chloride) for acylation chemistry.
• Cross-coupling surrogates: Convert C–Cl to C–B (via radical borylation) or to C–Sn/C–Si intermediates (radical or Ni-catalyzed routes) as precursors to further C–C bond formation.

Use contexts:

• Building block for halogenated lipid analogs, tethered linkers, and surface modifiers where a terminal handle (C8 position) and an internal electrophile enable sequential, regioselective elaboration.

Reaction Conditions

General literature guidance (representative, not item specifications):

• Amide coupling: HATU (1.1–1.5 equiv), amine (1.5–2.0 equiv), DIPEA (2–4 equiv) in DMF or DCM, 0–25 °C, 1–12 h. For sterically hindered partners, use T3P (50% in EtOAc) with mild heating (40–60 °C).
• Esterification:
  • Steglich: DCC (1.1 equiv), catalytic DMAP (0.1 equiv) in DCM/DMF, 0–25 °C, 2–16 h.
  • Fischer: ROH as solvent, catalytic H2SO4 or p-TsOH, reflux with water removal (Dean–Stark or sieves), 2–24 h.
• SN2 at C8 (primary chloride): Nucleophile (2–4 equiv) in DMF/DMSO/MeCN, 40–80 °C, 2–24 h; add KI (0.1–0.5 equiv) for in situ iodide exchange to accelerate displacement. Example nucleophiles: NaN3, NaSR, NaOEt.
• SN2 at C6 (secondary chloride): Stronger nucleophiles (e.g., NaN3, LiBr/KI for Finkelstein activation) and elevated temperature (80–120 °C in DMSO/NMP). Consider PTC (TBAB/TBAI) in toluene/CH2Cl2 with aqueous base for biphasic reactions. Monitor for E2 (alkene formation) and adjust base strength accordingly.
• Acid chloride formation: SOCl2 (2–4 equiv) with catalytic DMF in DCM or neat, 0–25 °C, 0.5–3 h; quench and handle under inert atmosphere.
• Dehalogenation (selective): Zn/AcOH or catalytic hydrogenation (Pd/C, H2) at rt–50 °C can remove one or both chlorides; monitor carefully to avoid over-reduction.

Workup and purification:

• Quench couplings with dilute aqueous base; extract into organic solvent. For highly lipophilic derivatives, use brine washes and silica gel with gradient hexanes/EtOAc or toluene/EtOAc. Confirm integrity by NMR (diagnostic –CH2Cl at ~3.4–3.6 ppm; –CHCl– at ~3.6–4.0 ppm, literature ranges).

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 guidance (literature/industry practice; defer to SDS for authoritative instructions):

• Likely hazards: Irritation to skin, eyes, and respiratory tract typical of low-molecular-weight carboxylic acids. Halogenated organics may present additional environmental hazards; avoid release to the environment.
• Personal protective equipment (PPE): Lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles. Use in a fume hood to avoid inhalation of vapors/aerosols.
• Handling: Avoid contact with bases unless neutralization is intended; heat and strong nucleophiles can promote substitution at the alkyl chloride positions. Prevent moisture ingress during moisture-sensitive transformations (couplings, acid chloride formation).
• Incompatibilities: Strong bases (can induce elimination/substitution), strong oxidizers (may cause vigorous reaction), strong reducing agents (risk of dehalogenation), and reactive metals.
• First aid overview: In case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do NOT induce vomiting unless directed by medical personnel. Seek medical attention in all cases.
• Fire safety: Use CO2, dry chemical, or foam extinguishers. Combustion may release HCl and other corrosive/irritant gases; firefighters should wear SCBA.
• Spill response: Contain, absorb with inert material, and dispose per local regulations. Prevent entry into drains.

Always consult the product SDS before use.

Solvent Selection

Polarity and miscibility (general, literature-based):

• Polarity class: Moderately nonpolar organic acid with enhanced lipophilicity from two chlorines.
• Expected solubility: Good in chlorinated solvents (DCM, chloroform), esters (EtOAc), ethers (THF, MTBE), ketones (acetone, MEK), and alcohols (MeOH, EtOH). Poor water solubility unless converted to its carboxylate (e.g., Na+, K+ salts).

Selecting solvents by task:

• Amide coupling (HATU/EDC/DIC): DMF, DCM, or acetonitrile offer good solubility; add base (DIPEA) and molecular sieves if needed.
• Esterification (Fischer): Toluene or the desired alcohol as solvent with acid catalysis; remove water by Dean–Stark or molecular sieves.
• SN2 substitutions at C8 (primary chloride): Polar aprotic solvents (DMSO, DMF, NMP, MeCN) accelerate displacement by anionic nucleophiles (e.g., azide, thiolate).
• SN2 at C6 (secondary chloride): Favor strong nucleophiles, higher temperatures, and polar aprotic media; consider phase-transfer catalysis (PTC) for heterogeneous systems.
• Aqueous workup: Transform to carboxylate with NaHCO3/Na2CO3 for extraction control; re-acidify to recover the acid.

Comparison notes:

• Versus non-halogenated C8 acid: The dichloro derivative is more soluble in chlorinated/aromatic solvents and less in water; it may show higher retention in RP-HPLC.
• For green choices, consider 2-MeTHF or CPME in place of DCM/THF when compatible with reactivity (see Green Alternatives).

Storage and Reconstitution

Item-specific storage conditions:

• Storage Conditions: Room temperature (as provided). Store tightly closed in a dry, well-ventilated place away from sources of ignition and incompatible materials.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General guidance:

• Protection: Keep container tightly sealed to minimize moisture uptake and oxidative degradation. For long-term storage, consider an inert atmosphere (nitrogen/argon) especially if frequent opening is expected.
• Stability: Halogenated aliphatic acids are generally stable at ambient conditions; avoid strong bases/acids and elevated temperatures that can induce substitution or elimination.
• Reconstitution/solubility: Dissolve in common organic solvents such as dichloromethane, chloroform, THF, ethyl acetate, methanol, ethanol, or acetonitrile. For aqueous systems, convert to the sodium/potassium carboxylate or use a co-solvent approach.
• Freeze–thaw: Not typically applicable unless preparing concentrated stock solutions; if solutions are stored, keep in amber vials at 2–8 °C or −20 °C depending on solvent volatility, and allow to warm to room temperature before opening to prevent moisture condensation.

Research use note: For research use only.

Structure and Identity

Overview: 6,8-Dichlorooctanoic acid is a halogenated medium-chain fatty acid bearing a terminal and an internal chloro substituent on an octanoic acid backbone.

Item-specific (from Product Data):

• SKU: D997349
• Product Name: 6,8-dichlorooctanoic Acid
• CAS: 41443-60-1
• PubChem CID: 9964447
• InChIKey: 129777 (as provided)
• SMILES: 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 structural information (for reference only):

• Typical molecular formula (literature): C8H14Cl2O2
• Typical molecular weight (literature): ~213.10 g/mol
• Representative SMILES (literature): O=C(O)CCCC(CCl)CCCl
• Functional groups: carboxylic acid (–CO2H), two alkyl chlorides (one secondary at C6 and one primary at C8).
• Structural description (2D): A linear C8 chain terminated by a carboxylic acid at C1; chlorines attached at C6 (secondary carbon within the chain) and at C8 (terminal methylene replacing the usual methyl). No defined stereocenters if substitution occurs on methylene carbons; the C6 position can become stereogenic upon substitution reactions.

Notes:

• The item-specific identifiers above should be used when cross-referencing. Literature data are provided to guide interpretation and method development and are not item specifications.

Synthetic Utility

Functional handles and strategy:

• Carboxylic acid (C1): Amenable to activation (acid chlorides, mixed anhydrides) for acylation; standard peptide-coupling chemistry for amide formation; esterification for protecting-group or pro-moiety installation.
• Primary alkyl chloride (C8): High SN2 propensity for nucleophile introduction (N, O, S, Se, C nucleophiles). Ideal for installing azides (→ amines), thioethers, ether linkages, or for anchoring to solid supports.
• Secondary alkyl chloride (C6): Moderately reactive; requires stronger nucleophiles or activation (e.g., iodide exchange, Lewis acid catalysis) and careful conditions to suppress E2.

Retrosynthetic value:

• Serves as a convergent node to generate ω-functionalized octanoic acid derivatives and internally substituted motifs after differential functionalization of the two C–Cl sites.
• Can be diversified into bifunctional linkers that present a terminal handle and a carboxylate for bioconjugation or materials grafting.

Named/standard reactions (general):

• Steglich esterification (DCC/DMAP), HATU/HBTU/EDC couplings, SOCl2-mediated acid chloride formation, Mitsunobu-type inversions after forming the corresponding alcohol (via substitution and reduction), and radical dehalogenations (Bu3SnH/AIBN or modern tin-free methods).

Analytical and protection:

• Protect the acid (as methyl/benzyl ester) before executing base-sensitive substitutions at C6/C8 to minimize side reactions; deprotect under mild conditions (saponification or hydrogenolysis).

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and is not an antibody, enzyme, or biological with defined binding targets. No target, epitope, clone, or species specificity information is provided for this item.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.