2-Chloronaphthalene-d , CAS No.93951-84-9

CAS: 93951-84-9 Cat. No.: C1445404 Fórmula: C₁₀D₇Cl Peso molecular: 169.66

Storage

Store at 2-8°C

Shipped In

Wet ice

Visão geral

2-Chloronaphthalene-d 7 is the deuterium labeled 2-Chloronaphthalene.

Specifications

Condições de armazenamento de armazenamento

Store at 2-8°C

Enviado em

Wet ice

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

• Peso molecular: 169.66

Application Protocols

No item-specific, validated protocols are provided in the Product Data. The following are general starting points; adapt to your SOPs.

• GC–MS internal standard (general):

  • Prepare a primary stock (e.g., 1–10 mg/mL) in a suitable solvent such as isooctane, toluene, or acetonitrile. Store cold (2–8 °C) and protect from evaporation.
  • Spike samples and calibration standards to yield constant internal standard concentration (e.g., 50–200 ng/mL, method-dependent).
  • Monitor a characteristic ion for d1 distinct from the native analyte and 13C pattern; verify ion ratios.

• LC–MS internal standard (general):

  • Use water-miscible co-solvent (acetonitrile, isopropanol). Confirm analyte retention on reversed-phase columns despite hydrophobicity; may require high organic content.
  • Validate matrix effects and recovery; ensure no H/D exchange during sample prep.

• Cross-coupling reaction (general):

  • Combine 1.0 equiv 2-chloronaphthalene-d, 1.2–1.5 equiv coupling partner, 2–3 equiv base, and 1–3 mol% Pd catalyst in toluene/dioxane. Heat 100–120 °C under N2 until completion by GC or LC. Work up and verify deuterium content by 2H NMR/HRMS.

These are illustrative, literature-style procedures. Always consult institutional SOPs and adjust for scale and instrumentation.

Biological Roles

This product is a deuterium-labeled polycyclic aryl chloride intended for chemical analysis and synthesis. It does not possess a defined biological role in cells or organisms.

General context (literature):

• Naphthalene derivatives can interact with lipid phases due to hydrophobicity, but 2-chloronaphthalene is not a physiological metabolite. Deuteration does not introduce a new biological function; it primarily aids analytical discrimination (MS/NMR).
• In environmental toxicology, chlorinated aromatics may display persistence and bioaccumulation; any such discussion is general and not specific to this SKU. No biological pathway participation is relevant here.

Use guidance:

• For research use only. Not for diagnostic, clinical, or food use.
• If used in biological matrices for method development, validate recovery, matrix effects, and isotopic fidelity (no H/D exchange) under sample prep conditions.

Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet if any biological testing is provided (typically none).

Buffer Applications

Not typically applicable. 2-Chloronaphthalene-d is a hydrophobic, nonionic organic compound and does not function as a buffer or pH modifier.

Practical note:

• When spiking into aqueous buffers for analytical recovery experiments, pre-dissolve in a water-miscible organic co-solvent (e.g., acetonitrile, isopropanol) and keep organic content consistent across standards and samples to avoid phase separation and adsorption losses.
• Verify that the chosen co-solvent does not promote H/D exchange under the conditions used (generally minimal for aromatic C–D bonds, but strong bases/acids and high temperature should be avoided).

Green Alternatives

Context: As a labeled aryl chloride, 2-Chloronaphthalene-d is typically used in micro- to milligram-scale analytical workflows, where green chemistry focuses on solvent choice and minimizing halogenated waste rather than replacing the analyte.

• Greener choices for solvent/media (general):

  • Prefer 2-MeTHF, CPME, toluene, or anisole over chlorinated solvents for coupling reactions when compatible.
  • For high-temperature reactions, anisole or diphenyl ether can be greener alternatives to chlorinated aromatics, subject to solubility and reactivity.

• Waste minimization:

  • Use the non-deuterated analogue as reaction solvent to avoid unnecessary consumption of labeled material.
  • Apply microscale coupling and flow chemistry to reduce solvent and energy use.

• Comparison snapshot (literature/general):

  • 2-Chloronaphthalene vs. toluene: higher bp and often better solvency but worse environmental persistence and more challenging disposal.
  • 2-Chloronaphthalene vs. anisole: similar high-bp utility; anisole offers better biodegradability and lower aquatic toxicity potential.

• Analytical alternatives:

  • Where a labeled internal standard is required for regulatory methods, deuterated analogues are standard. If flexibility exists, consider 13C-labeled standards, which eliminate back-exchange risks; availability and cost may differ.

Note: No greener “substitute compound” exists for isotopic-tracer applications that require structural identity; focus on greener solvents, reduced scale, and efficient workups.

Pharmaceutical Uses

This material is not used as a therapeutic agent. As a deuterated analytical standard or synthetic intermediate, its roles in pharmaceutical R&D are limited to research contexts.

General formulation/CMC context (literature/practice):

• Internal standards: Deuterated analogues are commonly employed in bioanalytical LC–MS/MS to support method validation (selectivity, accuracy, precision) for monitoring related analytes or impurities. If 2-chloronaphthalene is monitored (e.g., impurity or process residual), the d-analogue can be used as a stable isotope internal standard.
• Reference materials: May serve in system suitability tests for GC–MS or to challenge extraction/recovery steps from hydrophobic matrices.
• Excipient status: None; not a pharmacopeial excipient. No monograph or compendial grade is indicated.

Item-specific regulatory status and grades: Not specified for this item; refer to CoA/Spec Sheet.

Compliance note: For research use only. Not for use in humans or clinical diagnostics.

Physical Properties

Item-specific values (from Product Data):

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

Literature/typical properties for 2-chloronaphthalene (unlabeled; for context only):

• Physical state: typically a colorless to pale yellow liquid at ambient conditions (literature).
• Boiling point: approximately 259–262 °C (literature).
• Melting point: around −1 to +1 °C (literature).
• Density (20–25 °C): about 1.2–1.3 g/mL (literature).
• Water solubility: very low; essentially insoluble in water (literature). Miscible with many nonpolar/aprotic organic solvents (literature).
• LogP: high (hydrophobic polycyclic aryl chloride; literature qualitative assessment).
• Refractive index (nD): typical of chlorinated aromatics, ~1.60–1.63 (literature).

Deuterium effect note (general):

• Monodeuteration does not materially change bulk physical properties (bp, mp, nD) relative to the protiated analogue; any differences are within typical analytical uncertainty. Exact values for this specific labeled item are Not specified for this item; refer to CoA/Spec Sheet.

Analytical characterization suggestions (general):

• 1H NMR will show reduced integral at the labeled position; 2H NMR (76 MHz) confirms D incorporation. GC–MS exhibits an M+1 isotopic shift for d1 vs protiated material. FT-IR may show attenuated C–H stretches and C–D stretch near ~2200–2300 cm−1 (literature).

Quality and Grades

Item-specific quality attributes from Product Data:

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

Interpretation and guidance (general for deuterated aromatics):

• Isotopic labeling: For deuterated reference materials, two critical specifications are typically reported on the CoA—(1) isotopic enrichment (%D at the labeled position, and total %D for the molecule), and (2) chemical purity (% by GC/HPLC/1H NMR). This listing does not specify those values; consult the CoA for this lot.
• Analytical grade vs. research grade: Deuterated aromatics for spectroscopy commonly target ≥98% chemical purity and high isotopic enrichment; HPLC or GC area percent is often used. If UV transparency is relevant (e.g., LC–UV), an “HPLC grade” claim would imply low baseline noise in the 200–400 nm range. No such claim is provided here.
• Residual protium and solvent: Residual non-deuterated 2-chloronaphthalene or other isomers/solvents can affect quantitation in isotope-dilution experiments; reviewers should check residual solvent content and water content on the CoA if reported. Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: None are indicated in the Product Data. If stabilizers are used, they will be disclosed on the CoA.

Recommendation: When using as an internal standard, document isotopic purity and assign response factors accordingly. Retain CoA for traceability.

Reaction and Applications

Role of 2-Chloronaphthalene-d (general guidance for deuterated aryl chlorides):

• Isotopic internal standard:

  • GC–MS/LC–MS quantitation of 2-chloronaphthalene in environmental samples (sediments, oils): the d1 analogue provides co-elution with a distinct mass channel (M+1) for isotope dilution. Ensure isotopic enrichment is sufficient to avoid overlap with natural 13C patterns; verify on CoA.
  • NMR standard: 2H NMR signal confirms sample integrity; 1H NMR shows reduced integral at the labeled site.

• Cross-coupling precursor (literature):

  • Suzuki–Miyaura, Buchwald–Hartwig, Negishi, and Kumada couplings can convert the aryl chloride to labeled biaryls/arylamines. Aryl chlorides generally require stronger catalysts/ligands (e.g., Pd/XPhos, Pd/BrettPhos, Pd/BINAP, or Ni-based systems) and elevated temperatures.

• Metalation/functionalization (literature):

  • Direct lithium–halogen exchange is inefficient for aryl chlorides; alternative strategies include Ni-catalyzed borylation (to labeled boronate esters) or directed ortho-metalation of suitably substituted derivatives, followed by cross-coupling.

• Mechanistic/isotope-effect studies:

  • The C–D bond enables kinetic isotope effect probes in electrophilic aromatic substitution or hydrogen-abstraction pathways on the naphthalene ring. Position-specific information requires known labeling site (not specified for this item).

Practical tips:

• Dry, oxygen-free conditions improve cross-coupling outcomes. Use high-boiling solvents (toluene, dioxane) and bases (K3PO4, Cs2CO3). Monitor deuterium retention under protic/basic conditions to avoid H/D exchange at elevated temperatures.

Reaction Conditions

General literature guidance for transforming aryl chlorides like 2-chloronaphthalene (apply with verification; adjust to scale and equipment):

• Suzuki–Miyaura coupling:

  • Catalyst: Pd2(dba)3 (1–2 mol%) + XPhos/BrettPhos (2–4 mol%) or precatalysts (e.g., Pd-PEPPSI).
  • Base: K3PO4, Cs2CO3, or Na2CO3 (2–3 equiv).
  • Solvent: toluene, 1,4-dioxane, or mixtures with water (5–20%).
  • Temperature/time: 90–120 °C, 6–24 h.
  • Notes: Degas solvents; use inert atmosphere. Aryl chlorides often need higher temperature than bromides/iodides.

• Buchwald–Hartwig amination:

  • Catalyst/ligand: Pd2(dba)3 or Pd(OAc)2 with tBuBrettPhos, RuPhos, or XPhos.
  • Base: NaOtBu, KOtBu, or Cs2CO3.
  • Solvent: toluene, xylene, tert-amyl alcohol, or dioxane.
  • Temperature: 90–130 °C.
  • Note: Bulky ligands facilitate oxidative addition to aryl chlorides.

• Ni-catalyzed borylation:

  • Catalyst: Ni(cod)2 with dtbpy or phosphine ligands.
  • Reagents: B2pin2 (1.5–2.0 equiv), base (KOAc).
  • Solvent: dioxane or DMAc.
  • Temperature: 60–100 °C.

• Environmental/analytical use:

  • For GC–MS internal standardization, spike levels commonly in the low ng/mL to µg/mL range depending on matrix and method sensitivity; verify linearity and ion ratios per method SOP.

All conditions above are literature-style guidance and not item-specific specifications. Confirm deuterium retention post-reaction.

Safety and Handling

Item-specific hazard data:

• GHS Classification, Signal Word, H-Statements, Pictograms: Not specified for this item; refer to SDS.

General safety considerations for aryl chlorides and chlorinated polycyclic aromatics (literature/practice guidance; not a substitute for SDS):

• Likely hazards: flammable liquid/combustible at elevated temperature; may cause skin/eye irritation; harmful if swallowed; harmful to aquatic life with long-lasting effects. Actual classification must be confirmed from the SDS for this SKU.
• Personal protective equipment: wear lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a chemical fume hood to control vapors/aerosols.
• Handling: avoid inhalation of fumes and contact with skin/eyes. Prevent release to the environment. Deuterated materials should be handled to avoid isotopic dilution/contamination if used as internal standards.
• Incompatibilities (general): strong oxidizers; strong electrophiles; reactive metals at elevated temperature. Avoid strong bases at high temperature which can promote dehalogenation.
• First aid overview: skin/eye contact—rinse with water for several minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; do not induce vomiting; seek medical attention. Follow site-specific procedures.
• Fire-fighting: use dry chemical, CO2, or foam. Combustion may produce HCl and phosgene under extreme conditions; firefighters should wear self-contained breathing apparatus.

Always defer to the current Aladdin SDS for authoritative safety, exposure limits, spill cleanup, and disposal guidance.

Solvent Selection

Applicability: 2-Chloronaphthalene-d is primarily a labeled aryl chloride substrate/standard rather than a routine solvent. However, it is a hydrophobic, high-boiling organic liquid and may occasionally be used as a high-temperature medium or reference.

• Polarity class (general): nonpolar/aprotic aromatic liquid; very low dielectric constant compared to polar aprotic solvents (literature for chlorinated aromatics).
• Miscibility (literature/general):
  • Water: immiscible.
  • Organic solvents: miscible with nonpolar and moderately polar organics (e.g., benzene/toluene, chlorinated solvents, ethers, esters). Limited H-bonding capacity.
• Practical selection notes:
  • Because of its high boiling point (literature ~259–262 °C for the protiated analogue), it can serve as a heat-transfer or high-temperature reaction medium when substrate solubility in toluene/xylene is inadequate.
  • Not recommended as a chromatography solvent or general-purpose reaction solvent due to persistence and environmental profile; choose toluene, xylene, 2-MeTHF, or CPME when possible.
• Comparison (general):
  • Versus toluene/xylene: higher bp and often better solvency for polycyclic aromatics; more challenging removal and less green.
  • Versus chlorobenzene: similar role but higher aromatic surface area; often slightly higher bp.

Note: When using this item as a solvent, consider that isotopic content may be unnecessary—use the non-deuterated analogue instead to conserve labeled material.

Storage and Reconstitution

Item-specific storage/shipping (from Product Data):

• Storage Conditions: Store at 2–8 °C.
• Shipped In: Wet ice.

Handling and storage guidance (general):

• Store tightly closed in the original container to minimize evaporative losses and adventitious contamination. If repeatedly accessed, consider aliquoting under inert gas to preserve isotopic integrity for long-term studies.
• Protect from prolonged light and heat. While not particularly light-sensitive, minimizing exposure is good practice for aromatic chlorides.
• Do not freeze unless required by your workflow; freezing viscous aromatic liquids can complicate handling and is unnecessary given the recommended 2–8 °C storage.
• Reconstitution: Not applicable; supplied neat (appearance not specified). If dilutions are needed for standards, prepare solutions in dry, compatible solvents (e.g., toluene, acetonitrile, isooctane) and store at 2–8 °C in sealed glass vials. Document solvent, concentration, and preparation date.
• Stability: Item-specific shelf life and assay stability are Not specified for this item; refer to CoA/Spec Sheet. For analytical standards, establish in-house stability-indicating methods (GC–FID/MS, 1H/2H NMR) and re-verify concentration periodically.

Research Use Note: For research use only.

Structure and Identity

Brief description: 2-Chloronaphthalene-d is the deuterium-labeled analogue of 2-chloronaphthalene, consisting of a naphthalene bicyclic aromatic ring system bearing a chlorine substituent at the 2-position and one aromatic hydrogen replaced by deuterium (position of D not specified).

• Item-specific identifiers (from Product Data):

  • CAS: 93951-84-9
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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.

• Structural features (general/literature description):

  • Core scaffold: fused polycyclic aromatic hydrocarbon (naphthalene; two benzene rings sharing an edge).
  • Functional groups: aryl chloride (C(sp2)–Cl); isotopic label (C–D) on the aromatic framework.
  • Regiochemistry: chlorine at the 2-position of the naphthalene nucleus (aka β-chloro relative to a ring fusion carbon).
  • Stereochemistry: none (achiral, planar aromatic system).

• 2D structure in words (general):

  • Two linearly fused benzene rings; at the 2-position (adjacent to the ring fusion carbon) resides a chlorine substituent. One ring hydrogen is replaced by deuterium (D). The aryl C–Cl bond is deactivated relative to bromide/iodide toward oxidative addition, consistent with aryl chlorides.

Notes:

• Exact labeling position and isotopic enrichment are not provided in the Product Data; consult the CoA/SDS for definitive identity attributes.

Synthetic Utility

Functional profile:

• Aryl chloride on a naphthalene scaffold provides an entry to diverse labeled derivatives via cross-coupling and substitution chemistry. The incorporated deuterium enables fate-tracking in synthesis and mechanistic studies.

Key transformations (literature/general):

• Suzuki–Miyaura coupling to form deuterium-labeled biaryls using aryl/alkenyl boron partners; catalysts such as Pd-PEPPSI-type, Pd/XPhos, or Pd/BrettPhos at 80–130 °C in toluene/dioxane-water mixtures.
• Buchwald–Hartwig amination to access labeled aryl amines with bulky dialkylbiaryl phosphine ligands and strong bases (NaOtBu, Cs2CO3).
• Ni-catalyzed borylation (e.g., with B2pin2) to generate deuterium-labeled naphthyl boronate esters, broadening downstream diversification via boryl cross-couplings.
• Direct nucleophilic aromatic substitution is generally disfavored on naphthalene unless additional activating groups are present; cross-coupling is usually preferred.

Retrosynthetic value:

• Serves as a labeled “linchpin” for constructing libraries where the naphthalene core is conserved and peripheral groups vary—maintaining the isotopic tag throughout.

Isotopic integrity:

• Aromatic C–D bonds are robust; nevertheless, avoid superacidic/superbasic media and elevated temperatures in protic solvents that could induce limited H/D exchange. Confirm D retention by 2H NMR or HRMS after multi-step sequences.

Target Specificity

Not applicable. This product is a small-molecule deuterated aryl chloride, not a biological targeting reagent, antibody, or probe with defined target specificity.

• Antigen/epitope/clone/isotype: Not applicable.
• Species reactivity: Not applicable.

For analytical applications, “specificity” is achieved via mass selectivity (MS) and chromatographic separation rather than biological recognition.