Chlorobenzene-d5 - ≥98 atom% D,≥97% , CAS No.3114-55-4

CAS: 3114-55-4 Cat. No.: C342726 Fórmula: C₆D₅Cl Peso molecular: 117.59 Beilstein Registry Number: 1866335 Número EC: 221-482-0

GRADE & PURITY ≥98 atom% D,≥97%

Synonyms

1-chloro(H)benzene | AKOS015888334 | Chlorobenzene D5 100 microg/mL in Methanol | Chlorobenzene, perdeutero- | Benzene-d5-, chloro- | Benzene-d5, chloro- | SCHEMBL1332470 | 1-Chloro(~2~H_5_)benzene | Pentadeuterochlorobenzene | Chlorobenzene-d5 | Chlorobe

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Descripción general

Chlorobenzene-d5 is a halogenated D5 chlorobenzene for proteomics research. It is a precursor to deuterated dyes, rubbers, and herbicides. It can be also be used to create DDT by reaction with chloral (trichloroacetaldehyde). It is used as a high-boiling solvent in industrial applications. It is usually synthesized by reacting D6 benzene with ferric chloride, sulfer dichloride, and anhydrous aluminum chloride, yielding Chlorobenzene-d5 and DCl.

Specifications

Sinónimos

1-chloro(H)benzene | AKOS015888334 | Chlorobenzene D5 100 microg/mL in Methanol | Chlorobenzene, perdeutero- | Benzene-d5-, chloro- | Benzene-d5, chloro- | SCHEMBL1332470 | 1-Chloro(~2~H_5_)benzene | Pentadeuterochlorobenzene | Chlorobenzene-d5 | Chlorobe

Especificaciones y pureza

≥98 atom% D,≥97%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C,Protected from light,Argon charged

Enviado en

Wet ice

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Pureza

≥98 atom% D,≥97%

Nombres e identificadores

Pubchem Sid

504759327

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504759327

Sonrisas canónicas

C1=CC=C(C=C1)Cl

IUPAC Name

1-chloro-2,3,4,5,6-pentadeuteriobenzene

InChIKey

MVPPADPHJFYWMZ-RALIUCGRSA-N

INCHI

1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H/i1D,2D,3D,4D,5D

Isómeros SMILES

[2H]C1=C(C(=C(C(=C1[2H])[2H])Cl)[2H])[2H]

Número ONU

1134

Grupo de embalaje

III

Peso molecular

117.59

Beilstein

1866335

Reaxy-Rn

605632

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=605632&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Chlorobenzenes
• Alternative Parents: Aryl chlorides Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Chlorobenzene - Aryl halide - Aryl chloride - Hydrocarbon derivative - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
• 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

Propiedades químicas y físicas

• Sensibilidad: Light sensitive；Moisture sensitive
• Índice de refracción: n20/D 1.522 (lit.)
• Punto de inflamación (°C): 24.0℃
• Punto de ebullición (°C): 130-130.5° C
• Peso molecular: 117.590 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 117.039 Da
• Monoisotopic Mass: 117.039 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 46.100
• Isotope Atom Count: 5
• 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 item-specific validated protocols are provided. Typical research uses include:

• GC/MS internal standardization
  • Prepare calibration standards with fixed chlorobenzene-d5 concentration across the curve; integrate target analyte to IS response ratios to correct for variability.
• NMR solvent use
  • Dry solute thoroughly; acquire spectra at temperatures up to near the solvent’s bp as needed; reference chemical shifts using external standards; confirm residual 1H content from CoA.
• Cross-coupling substrate
  • Apply standard aryl chloride coupling conditions with label-retaining workup; verify isotopic integrity by MS and, if needed, 2H NMR.

For detailed, method-specific protocols, consult primary literature and validate under your laboratory’s QA procedures.

Biological Roles

Chlorobenzene-d5 is a small, deuterium-labeled aromatic solvent/standard and does not possess intrinsic biological function.

• General/literature context

  • Not a metabolite or cofactor in known biochemical pathways; lacks functional groups typical of biological building blocks.
  • Deuterium-labeled compounds can be used as tracers in metabolism and environmental fate studies; the C–D bonds enable tracking by MS without altering electronic structure significantly.
  • Because the isotopic substitution minimally perturbs chemical properties, chlorobenzene-d5 can serve as an internal standard to normalize extraction and ionization variability across biological matrices in analytical workflows.

• Practical implications

  • For bioanalytical method development (e.g., quantifying chlorobenzene contamination or related aromatics), chlorobenzene-d5 can be spiked as a surrogate/internal standard to assess recoveries and matrix effects.
  • No buffering capacity, enzymatic activity, or receptor binding relevance is expected.

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

Buffer Applications

This product is a nonpolar, deuterated aromatic solvent/standard and is not used to prepare aqueous buffers. It has no buffering capacity. For method development involving biological matrices, consider this material as an internal standard rather than a buffer component.

Green Alternatives

Deuterated chlorobenzene is primarily chosen for its isotopic label rather than for green solvent credentials. For non-isotopic applications, greener alternatives may be more appropriate.

• Considerations

  • Halogenated aromatics raise environmental concerns (persistence and aquatic toxicity). If isotopic labeling is not required, prefer less hazardous solvents.

• Comparative options (literature; general guidance)

  • Toluene or 2-MeTHF (unlabeled): Lower environmental impact, good solvency for many organics; 2-MeTHF is biorenewable and has favorable EHS profile.
  • Cyclopentyl methyl ether (CPME): Broad solubility, low peroxide formation, water-tolerant; suitable for many metal-catalyzed reactions.
  • Propylene carbonate: Polar aprotic, high bp, low volatility; not suitable for all organometallics but greener for certain transformations.

• Tradeoffs

  • None of the greener options replicate the isotopic benefits of chlorobenzene-d5 for MS/NMR. When isotope labeling is essential, minimize usage, implement closed systems, and ensure proper waste segregation and disposal.

• Practical steps

  • Evaluate solvent selection guides (e.g., Pfizer/ACS GCI) for your specific transformation.
  • If using chlorobenzene-d5 purely as a solvent, consider whether toluene-d8 or other deuterated, less hazardous options meet your technical needs.

Pharmaceutical Uses

• Context (general; no therapeutic claims)

  • Deuterated small molecules like chlorobenzene-d5 may be used as analytical internal standards in pharmaceutical quality control (e.g., GC/MS methods) to ensure accurate quantitation and to track extraction/processing losses.
  • As a solvent or process aid, chlorobenzene-class solvents are rarely preferred in GMP manufacturing due to EHS and ICH Q3C considerations; however, they may be encountered in R&D scale reactions. When used, robust removal and residual solvent testing are required.

• Excipient/formulation role

  • None. This material is not an excipient and is not intended for formulation use.

• Documentation

  • Verify isotopic enrichment and chemical purity on the CoA for validated analytical methods.
  • Ensure SDS-based risk assessments and appropriate handling controls are in place for regulated environments.

Physical Properties

Note: No item-specific specifications were provided; values below are literature/general for chlorobenzene-d5 or, where noted, for chlorobenzene as an approximate guide. Do not use as product specifications.

• Item-specific values

  • BP/MP/density/RI/solubility/logP/pKa: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general values (reference only)

  • Boiling point: ~131 °C (literature; similar to chlorobenzene; deuteration causes negligible shift)
  • Melting point: ~−45 °C (literature)
  • Density: ~1.11–1.12 g/mL at 20–25 °C (literature; chlorobenzene ≈1.106 g/mL)
  • Refractive index (n20D): ~1.524–1.526 (literature for chlorobenzene)
  • Water solubility: ~0.5 g/L at 25 °C (very slightly soluble; literature for chlorobenzene)
  • LogP (octanol/water): ~2.8–2.9 (literature)
  • Dielectric constant (ε, 25 °C): ~5.6 (literature for chlorobenzene)
  • Vapor pressure (25 °C): ~11–12 mmHg (literature for chlorobenzene)
  • pKa: Not applicable (neutral aryl chloride; no acidic/basic centers under normal conditions)

• Practical notes

  • Low polarity, aromatic, high-boiling solvent/profile; miscible with most organic solvents and immiscible with water (literature). Always confirm item-specific values on the CoA for critical applications (e.g., density-based dosing, GC headspace method setup).

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades for deuterated solvents/standards (general guidance)

  • Isotopic enrichment: For deuterated aromatics, enrichment (e.g., ≥98 atom % D) is often specified for analytical/NMR applications. Absence of this value here means you should consult the CoA for exact enrichment and residual protium content.
  • Chemical purity: May be stated as GC area% or as ppm-level impurities (water, halogenated byproducts, stabilizers). Since no specification is provided, verify the latest CoA if trace-level impurities or water content are critical to your method.
  • Stabilizers: Some aromatic solvents may be supplied inhibitor-free; others may contain trace stabilizers. None are listed here—assume no stabilizer unless the CoA indicates otherwise.

• What matters for this item type

  • For NMR or GC/MS internal standard use, key attributes include isotopic enrichment, residual solvent signals, water content, and UV background if used in spectroscopic contexts.
  • For use as a labeled aryl chloride substrate in cross-coupling, confirm trace metal content and halide purity only if your catalyst system is sensitive.

Consult the Aladdin CoA/Spec Sheet for this lot to confirm isotopic enrichment, chemical purity, and any stabilizer information before regulated or quantitative applications.

Reaction and Applications

• Analytical and isotopic uses

  • Internal standard: Deuterated aromatic standard for GC/MS quantitation, enabling isotope-dilution methods and correction for extraction/ionization variability.
  • NMR solvent: Usable for elevated-temperature 1H/13C measurements of aromatic or halogenated analytes; residual signals are deuterium-based, minimizing interference in 1H spectra.
  • Mechanistic probes: Aromatic C–D labeling supports kinetic isotope effect experiments and mapping of H/D exchange under catalytic conditions.

• As a labeled aryl chloride substrate (literature/general)

  • Cross-coupling: Participates in Suzuki–Miyaura, Buchwald–Hartwig, Kumada, Negishi, and Stille couplings under Pd or Ni catalysis, with the C–D bonds largely retained—facilitating mass balance by MS and site-specific NMR tracking.
  • Directed metalation: Harsh base-mediated lithiation (e.g., with t-BuLi) can promote H/D exchange or benzyne pathways; use with caution if preserving deuterium labeling is essential.
  • Nucleophilic aromatic substitution: Typically requires strong EWGs; unactivated chlorobenzene is resistant to SNAr, useful as a negative control in labeling studies.

• Practical tips

  • If preserving deuterium labeling, avoid strong bases, protic media, or heterogeneous catalysts known to catalyze H/D exchange on arenes.
  • For cross-couplings, ligand-enabled activation of aryl chlorides (e.g., biaryl phosphines, NHCs) reduces temperature and preserves labeling by minimizing side reactions.
  • Validate isotopic integrity pre- and post-reaction by GC/MS or LC/HRMS.

Reaction Conditions

General literature guidance for aryl chloride transformations and analytical usage; verify for your specific system. These are not product specifications.

• Cross-coupling (literature examples)

  • Suzuki–Miyaura: Pd2(dba)3 or Pd(OAc)2 (1–2 mol%) with SPhos/XPhos (2–4 mol%); base K3PO4, K2CO3, or Cs2CO3; solvent dioxane/toluene/THF; 60–100 °C; 2–16 h; often 70–95% yields with competent partners. Label retention on the ring expected.
  • Buchwald–Hartwig amination: Pd2(dba)3 or Pd(OAc)2 with BrettPhos or RuPhos; NaOtBu/Cs2CO3; toluene or dioxane; 80–110 °C; 4–18 h.
  • Kumada/Negishi/Stille: Ni or Pd catalysts; ethers or aromatics as solvents; 0–80 °C for Kumada; 40–90 °C for Negishi/Stille.

• Hydrogenation/H/D exchange

  • Pd/C or Pt catalysts under H2 can induce loss of deuterium via exchange. If label preservation is required, avoid heterogeneous hydrogenation or perform under D2 and monitor.

• Analytical usage

  • GC/MS internal standard: Spike at known concentration (e.g., 10–500 ng/mL ranges common) to match analyte response; monitor characteristic m/z cluster shifted by +5 Da versus chlorobenzene.
  • NMR: As a deuterated solvent, lock/shim performance is adequate; high bp allows VT experiments. Verify residual protium signal on CoA before quantitative 1H work.

• Workup considerations

  • Avoid protic quench conditions at elevated temperatures that could promote H/D scrambling. Dry, neutral workups help conserve labeling.

Safety and Handling

• Item-specific hazard data

  • GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to the SDS for authoritative information.

• General safety considerations for chlorobenzene-class solvents (literature/guidance)

  • Flammability: Aromatic chlorinated solvents can be combustible; keep away from ignition sources. Confirm actual flammability category on SDS.
  • Toxicity/irritation: May cause skin/eye irritation and central nervous system effects upon significant exposure. Avoid inhalation of vapors and prolonged skin contact.
  • Environmental: Harmful to aquatic life with long-lasting effects is reported for related compounds; prevent release to the environment.

• PPE and handling

  • Use in a fume hood with appropriate ventilation.
  • Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles; consider double-gloving for extended handling.
  • Avoid contact with strong bases or organometallic reagents if preservation of deuterium labeling is important, as harsh conditions can promote H/D exchange on the ring.

• Storage and incompatibilities

  • Storage (from Product Data): Store at 2–8 °C, protected from light, under argon. Shipped on wet ice.
  • Keep containers tightly closed; segregate from strong oxidizers and strong bases. Ground/bond if transferring bulk liquid.

• First aid (general)

  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always defer to the product SDS for definitive hazard classifications and response procedures.

Solvent Selection

Chlorobenzene-d5 behaves similarly to chlorobenzene as a solvent, with deuteration minimally affecting bulk properties. Selection should be based on its aromatic, moderately polar, high-boiling profile—and on the need for isotopic labeling.

• Polarity and miscibility (literature/general)

  • Polarity class: Low-polarity, aromatic, aprotic solvent; dielectric constant ~5.6.
  • Miscibility: Miscible with common organics (ethers, aromatics, chlorinated solvents); immiscible with water; limited miscibility with alcohols.
  • Boiling point ~131 °C supports elevated-temperature reactions and high-T NMR acquisition when used as solvent.

• When to choose chlorobenzene-d5

  • As an NMR solvent for high-temperature spectra of polarizable aromatic substrates where non-deuterated solvent background must be minimized.
  • As a matrix or internal standard in GC/MS or LC/MS where deuterium labeling simplifies quantitation and corrects for matrix effects.
  • As a labeled reaction medium for mechanistic H/D-scrambling studies or kinetic isotope effect investigations.

• Alternatives and comparisons (literature; general)

  • Toluene-d8: Similar aromaticity, slightly lower bp (111 °C), broader availability as NMR solvent; non-halogenated.
  • 1,2-Dichlorobenzene-d4: Higher bp (~180 °C) for very high-temperature work; more polarizable, stronger solvency for some substrates.
  • Non-deuterated chlorobenzene: When isotopic labeling is unnecessary and cost or availability is a priority.

Confirm compatibility with solutes, catalysts, and analytical methods before selection.

Storage and Reconstitution

• Storage conditions (from Product Data)

  • Store at 2–8 °C.
  • Protect from light.
  • Maintain under argon (argon charged).
  • Shipped on wet ice.

• Handling and aliquoting

  • Open/dispense under inert gas where practical to limit moisture/oxygen ingress and to preserve isotopic integrity over time.
  • Use amber or foil-wrapped containers to minimize light exposure.

• Stability considerations

  • Aromatic C–D bonds are generally robust, but strong bases, catalytic hydrogenation, or high-temperature acidic/basic conditions can promote H/D exchange. Avoid such conditions if the deuterium label must be retained.
  • Keep container tightly sealed to prevent evaporation and contamination.

• Reconstitution

  • Supplied neat (liquid). No reconstitution required. If dilution is needed for analytical standards, use dry, compatible solvents and document concentration gravimetrically for traceable isotope-dilution assays.

Always refer to the CoA and SDS for lot-specific stability, purity, and safety guidance.

Structure and Identity

Chlorobenzene-d5 is the fully deuterated isotopologue of chlorobenzene, featuring a chlorinated benzene ring in which all five ring hydrogens are replaced by deuterium.

• Item-specific (from Product Data)

  • Product name: Chlorobenzene-d5
  • CAS: 3114-55-4
  • CID: 575975
  • InChIKey: 229674 (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 identifiers and structural description (for reference; not item specifications)

  • Typical molecular formula (literature): C6D5Cl
  • Typical average molecular weight (literature): ~117.57 g/mol
  • Representative SMILES (literature): [2H]c1c([2H])c([2H])c(Cl)c([2H])c1[2H]
  • 2D structural features: a six-membered aromatic ring bearing a chlorine substituent (sp2 C–Cl) para to two C–D bonds and meta/ortho to the remaining C–D positions; planarity and aromaticity retained; no stereogenic centers.

• Key functional elements

  • Aryl chloride functionality (electron-withdrawing; activates for cross-coupling under Pd/Ni catalysis).
  • Five aromatic C–D bonds suitable as isotopic labels for mechanistic tracing and analytical internal standards.

Synthetic Utility

Chlorobenzene-d5 functions both as a labeled solvent and as a labeled aryl chloride building block, allowing direct translation of established aryl chloride chemistry while tracking isotopic integrity.

• Functional group and reactivity

  • Aryl chloride: amenable to Pd- or Ni-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig amination, Kumada, Negishi, Stille). The aryl C–Cl bond is moderately reactive; ligand and catalyst choice is critical.
  • Aromatic C–D bonds: Typically robust under neutral conditions; serve as tracers in mechanistic studies. Under strong base or catalytic hydrogenation, H/D exchange can occur—useful intentionally, but a risk if the label must be preserved.

• Retrosynthetic value

  • Enables labeled versions of downstream products (biaryls, anilines, aryl ethers, aryl boronates) by retaining ring deuteration, facilitating MS-based quantitation and distribution mapping of label across transformations.

• Practical guidance

  • Employ modern ligands (e.g., biaryl phosphines, BrettPhos/SPhos/XPhos; or NHCs) for efficient activation of the C–Cl bond at 60–110 °C.
  • Choose bases and solvents that avoid H/D scrambling when preservation is key (e.g., avoid strong alkoxides at high temperature in protic media).
  • Confirm isotopic retention of the arene ring after transformation via HRMS and 2H NMR.

Target Specificity

Not applicable. This product is a small-molecule solvent/standard, not a biological targeting reagent (e.g., antibody, inhibitor, or probe with defined biomolecular specificity).

Preguntas frecuentes

What is the purity of this product?

This product is isotopically enriched to ≥98 atom% deuterium. Isotopic enrichment is a separate specification from chemical purity — a labelled compound has both. 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 2–8 °C, protected from light, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

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

The CAS Number is 3114-55-4, the molecular formula is C6D5Cl, and the molecular weight is 117.59 g/mol. InChIKey MVPPADPHJFYWMZ-RALIUCGRSA-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.