2,4-Xylidine-d , CAS No.1071170-27-8

CAS: 1071170-27-8 Cat. No.: X1440411 Fórmula: C₈H₅D₆N Peso molecular: 127.22

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

2,4-Xylidine-d6 is a deuterated labeled 2,4-Xylidine-d6.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

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

Nomes e identificadores

Peso molecular

127.22

Application Protocols

No item-specific, validated protocols were provided. The following are general, non-binding examples tailored to deuterated internal standards:

• LC–MS/MS internal standard preparation (general):

  • Prepare a primary stock (e.g., 1.0 mg/mL in MeOH or ACN) gravimetrically using anhydrous solvent.
  • Prepare a working solution (e.g., 100 ng/mL) in the initial mobile phase composition.
  • Spike a fixed volume into samples, calibration standards, and QCs to reach a consistent final concentration.
  • Verify co-elution and stable isotope response (no significant H/D exchange during sample prep).

• GC–MS derivatization (if volatility enhancement required):

  • Convert the amine to a volatile derivative (e.g., acylation with acetic anhydride) under anhydrous conditions; confirm the derivative retains the deuterium label at non-exchangeable positions.

These examples are for planning purposes only. Optimize and validate for your specific matrix, instrument, and regulatory requirements.

Biological Roles

This product is intended for research use only and is not a biological macromolecule. No intrinsic biological role is assigned in vivo for the deuterated isotopologue.

• General context (literature):

  • Anilines are xenobiotics in most biological systems and can undergo metabolic N-oxidation, N-acetylation, and ring hydroxylation via CYP-mediated pathways.
  • Deuterated analogs are widely used as tracers or internal standards in bioanalytical assays to quantify exposure, metabolism, or environmental occurrence of the corresponding non-deuterated compounds.
  • Stable-isotope labels facilitate accurate mass spectrometric quantitation in complex matrices (plasma, urine, environmental waters) by correcting for matrix effects and recovery.

• Practical guidance:

  • When used as an internal standard, ensure the deuterium label is positioned to minimize back-exchange or metabolic scrambling under sample preparation conditions.
  • Validate co-elution and consistent response factors between analyte and internal standard in your specific LC/GC method.

No organism-specific targets or pathways are claimed for this item.

Buffer Applications

Not typically applicable. 2,4-Xylidine-d is a small-molecule aromatic amine used as a labeled standard or building block, not as a buffering agent.

• Practical note: If handling as a salt for solubility, standard laboratory buffers (e.g., phosphate, acetate, formate) may be present in the mobile phase or sample matrix for analytical work, but the compound itself is not used to establish buffer capacity.

Green Alternatives

As a deuterated aniline, the compound itself is not readily substitutable when isotopic labeling is required. However, greener practices can be applied in its use:

• Solvent choices (general guidance):

  • Prefer EtOAc, 2-MeTHF, cyclopentyl methyl ether (CPME), or MeOH over chlorinated solvents where feasible.
  • For extractions, MTBE or EtOAc can substitute for DCM/CHCl3 in many workflows.

• Comparison (general, literature):

  • 2-MeTHF vs THF: 2-MeTHF is biomass-derived, less volatile, and often allows easier phase separations; THF forms peroxides more readily and has lower flash point.
  • CPME vs DCM: CPME offers broader liquid range and lower toxicity profile; DCM provides superior volatility for rapid concentration but with higher environmental/health concerns.

• Process considerations:

  • Minimize acid/base-catalyzed H/D exchange by using buffered, milder conditions; this also reduces corrosive reagent use.
  • Use microscale reactions and concentrated stock solutions to cut solvent volumes in analytical workflows.
  • Implement closed transfer systems to reduce VOC emissions.

Trade-offs: While greener solvents reduce environmental impact, they may alter analyte retention/ionization in LC–MS or reactivity/selectivity in synthesis; re-optimize conditions accordingly.

Pharmaceutical Uses

No therapeutic or clinical claims are made for this product. It is supplied strictly for research use.

• General formulation/analysis context (literature):

  • Deuterated small molecules are commonly used as internal standards in bioanalytical method development and validation (e.g., LC–MS/MS quantitation of anilines or their metabolites in preclinical samples).
  • In process development, labeled analogs can be used to track impurity fate and mass balance, or to investigate reaction mechanisms.
  • The compound is not an excipient and has no pharmacopeial monograph as such; any use in GMP settings would require in-house qualification and appropriate reference standard characterization.

• Documentation: For regulated analyses, retain CoA, isotopic enrichment data, and stability studies for the specific lot employed.

Physical Properties

• Item-specific (from Product Data):

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

• Literature values for the non-deuterated parent (2,4-dimethylaniline; for context only):

  • Typical BP: ~215–217 °C (literature).
  • Typical MP: ~−25 °C (literature).
  • Density: ~0.98 g/mL at 25 °C (literature).
  • Solubility: sparingly soluble in water; miscible with many organics (alcohols, ethers, aromatics) (literature).
  • pKa (anilinium conjugate acid): ~5.1; basicity weaker than aliphatic amines (literature).
  • LogP: ~2.3–2.6 (literature, method-dependent).
  • Refractive index (n20 D): ~1.55 (literature).

Notes:

• Deuteration typically causes negligible changes to bulk physical properties; exact values for this item depend on labeling pattern and should be verified on the CoA/Spec Sheet.
• Do not treat literature values as specifications; they are provided to guide handling and method development.

Quality and Grades

• Item-specific (from Product Data):

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

• Context and expectations for deuterated standards (general):

  • Isotopic purity: For deuterated reference materials, both chemical purity and isotopic enrichment (e.g., %D at labeled positions) are critical. These parameters determine suitability for quantitative LC/GC–MS as internal standards and for mechanistic kinetic isotope effect studies.
  • Residual protio content: Elevated H content at labeled positions can bias isotope-dilution assays; CoA should report D incorporation and distribution.
  • Trace impurities: Oxidation products (e.g., nitroso, azo, or anilide derivatives) and residual solvents should be controlled; low UV background and narrow GC/MS profiles are desirable.
  • Documentation: Expect CoA to include chemical purity (e.g., GC/HPLC area %), isotopic pattern (MS), and water/volatile content when applicable. For this item, consult the CoA/Spec Sheet for exact specifications.

• Stabilizers:

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

Interpretation tip: If intended for quantitative mass spectrometry, select lots with reported isotopic enrichment and minimal deuterium scrambling under your sample prep conditions.

Reaction and Applications

• Analytical uses of deuterated anilines (general):

  • Internal standards in LC–MS/GC–MS for quantifying 2,4-xylidine or related anilines; co-elution with mass shift enables accurate isotope-dilution analysis.
  • Mechanistic probes: Evaluate kinetic isotope effects, hydrogen/deuterium exchange, and pathways of electrophilic aromatic substitution or oxidation.

• Synthetic/derivatization applications (general):

  • Salt formation with mineral or organic acids for purification/crystallization.
  • Acylation/sulfonylation to give amides/sulfonamides (e.g., formation of deuterium-labeled acetanilides or tosylates).
  • Diazonium chemistry (from the aniline, via nitrosation then Sandmeyer-type substitutions) to introduce labeled aryl derivatives while retaining deuterium at non-exchangeable positions.
  • Buchwald–Hartwig N-arylation or Ullmann-type amination using the aniline as nucleophile to construct higher-order diarylamines.

• Practical tips (general):

  • Avoid strong acids/bases and protic media at elevated temperature if preserving labile deuterium (e.g., at amino or benzylic positions). Deuterium at non-exchangeable aromatic carbons is typically robust.
  • For analytical standards, prepare and store stock solutions under inert atmosphere in dry, anhydrous solvent; document concentration gravimetrically.
  • Verify isotopic integrity by MS before and after synthetic steps if the deuterium label is critical to your study.

No item-specific application notes were provided; consult the CoA for any tested uses.

Reaction Conditions

General guidance (literature; optimize for your system):

• Acylation/sulfonylation of anilines:

  • Solvents: DCM, THF, or pyridine; bases: triethylamine or NaHCO3; 0–25 °C; minutes to hours; typically high yields. Avoid aqueous acidic workups if preserving N–D.

• Buchwald–Hartwig amination (using this aniline as nucleophile):

  • Catalysts: Pd2(dba)3 or Pd(OAc)2 with ligands (e.g., XPhos, tBuBrettPhos); base: NaOtBu, Cs2CO3; solvent: toluene, dioxane, or tAmOH; 60–110 °C; 2–24 h.
  • Note: Protect amine if competitive binding inhibits coupling; monitor for H/D exchange at benzylic/N positions depending on conditions.

• Diazotization/Sandmeyer:

  • Form diazonium salt with NaNO2/HX at 0–5 °C; subsequent substitution with CuX or other nucleophiles; keep temperatures low to maintain label and minimize side reactions.

• Electrophilic aromatic substitution:

  • Directing effects from –NH2 and methyls favor ortho/para attack; Lewis/Brønsted acid catalysts can promote exchange at activated positions—use milder conditions to preserve deuterium.

• Analytical preparation:

  • Stock solutions: 0.1–1.0 mg/mL in MeOH, ACN, or DMSO; store cold and protected from moisture. Validate stability and isotopic composition by LC–MS.

These are literature-style conditions for typical anilines and should be adapted. For this item, verify deuterium placement to anticipate exchange risk.

Safety and Handling

• Item-specific (from Product Data):

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.
  • Storage Conditions: Store at −20 °C.
  • Shipping: Ice chest + ice pads.

• General safety guidance (aniline derivatives; literature):

  • Hazards: Aromatic amines can be harmful if swallowed, inhaled, or absorbed through skin; some can induce methemoglobinemia. Many are skin/eye irritants and sensitizers. Handle in a fume hood.
  • PPE: Lab coat, nitrile gloves (change regularly), splash goggles; consider double-gloving for extended contact. Avoid skin contact and inhalation.
  • Incompatibilities: Strong oxidizers, strong acids (can form salts; exotherm on neutralization), acyl/alkyl halides (reactive), nitrosating agents.
  • First aid (overview; follow SDS): Fresh air for inhalation exposure; rinse skin/eyes with water for ≥15 minutes; seek medical attention after significant exposure. Remove contaminated clothing.
  • Fire: Combustible organic liquid/solid; use CO2, dry chemical, or foam. Thermal decomposition may release nitrogen oxides.
  • Waste: Collect as halogen-free organic amine waste; dispose per local regulations.

Always consult the product-specific SDS for authoritative hazard and first-aid information.

Solvent Selection

• Compound class (general): aromatic primary amine (aniline), moderately nonpolar with a basic site; deuteration does not materially affect solubility class.

• Solubility/miscibility (literature, parent 2,4-xylidine):

  • Miscible with many organic solvents (DCM, EtOAc, ethanol, acetone, toluene, THF).
  • Limited water solubility; forms water-soluble ammonium salts under acidic conditions.

• Polarity profile (general):

  • Weak base (aniline); forms hydrogen bonds as donor/acceptor. Suitable for reversed-phase LC with modest retention; ionization can be tuned by mobile phase pH.

• Practical selection:

  • NMR: For structural verification, common solvents include CDCl3 or DMSO-d6; note that exchanging N–H/D signals may be broadened.
  • MS sample prep: MeOH, ACN, or IPA (with 0.1% FA for positive ESI) are typical. Minimize strong acids/bases if deuterium scrambling is a concern.
  • Workup/extraction: Extract into organic (e.g., MTBE, DCM). Protonate with dilute HCl to transfer to aqueous phase when desired; basify to re-extract free base.

• Comparison (general guidance):

  • Toluene vs THF: Toluene better for high-temp reactions; THF better for metalations but water-sensitive.
  • Protic (EtOH) vs aprotic (ACN): Choose protic solvents for salt handling and improved wettability; choose aprotic for basicity-sensitive transformations.

Storage and Reconstitution

• Item-specific (from Product Data):

  • Storage Conditions: Store at −20 °C.
  • Shipped In: Ice chest + ice pads.

• Practical storage guidance (general):

  • Keep container tightly closed under dry, inert atmosphere if possible to limit moisture and oxidative degradation typical of anilines.
  • For long-term storage, aliquot to minimize freeze–thaw cycles and headspace oxygen exposure.
  • Protect from strong light and acids/bases if preservation of labile deuterium (e.g., N–D, benzylic C–D) is important.

• Reconstitution/solution prep (general):

  • Use anhydrous solvents such as MeOH, ACN, DMSO, THF, or toluene depending on application. Record concentration gravimetrically for standards.
  • Allow material to equilibrate to room temperature in a desiccator before opening to avoid condensation. Reseal promptly after use.
  • For salt formation (if desired), use weak acids (e.g., HCl in ether/IPA) at low temperature and verify isotopic integrity by MS.

• Stability notes:

  • Confirm stability and isotopic composition periodically by LC/GC–MS, especially for analytical standards stored over months.
  • Follow any lot-specific guidance on the CoA/Spec Sheet regarding shelf life and solution stability.

Structure and Identity

Brief overview: 2,4-Xylidine-d is a deuterium-labeled isotopologue of 2,4-xylidine (2,4-dimethylaniline), typically used as an analytical standard or mechanistic probe.

• Item-specific (from Product Data):

  • Product Name: 2,4-Xylidine-d
  • CAS: 1071170-27-8
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/structural context (general):

  • Parent structure: 2,4-xylidine = 2,4-dimethylaniline, an aniline bearing methyl substituents at ortho (2) and para (4) positions relative to the amino group.
  • Core functional group: aniline (aromatic primary amine, –NH2 on benzene ring).
  • Isotopic labeling: the “-d” indicates replacement of one or more protium atoms (H) with deuterium (D); exact labeling position(s) and D-count are not specified in the Product Data.
  • 2D description: a benzene ring with –NH2 at C1, CH3 at C2 (ortho), and CH3 at C4 (para). In the deuterated isotopologue, specified H positions are replaced by D (pattern not provided here).

Synthetic Utility

• Functional group profile (general):

  • Aromatic primary amine enabling nucleophilic acylation/sulfonylation, diazotization, and transition-metal-catalyzed C–N coupling. Ortho/para methyl groups influence directing effects and sterics.

• Isotopic label leverage:

  • Site-specific deuteration enables tracing hydrogen transfer, probing electrophilic aromatic substitution regiochemistry, and measuring kinetic isotope effects.
  • The deuterium label on non-exchangeable positions (aromatic C–D) generally survives a wide range of conditions; N–D and benzylic C–D are more labile.

• Named transformations (literature):

  • Buchwald–Hartwig amination to form diarylamines.
  • Sandmeyer and related diazonium chemistry for aryl substitution while preserving non-exchangeable deuterium.
  • Electrophilic acylation/sulfonylation to prepare labeled amides/sulfonamides for standards.
  • Directed ortho-metalation adjacent to the aniline (after appropriate protection) can allow further labeled elaborations, subject to deuterium stability.

• Practical tips:

  • Protect the amine (e.g., acyl, Boc, sulfonyl) during harsh conditions to control reactivity and prevent H/D exchange.
  • Verify isotopic integrity by HRMS before/after steps critical to label placement.
  • Choose bases/solvents to balance reactivity with label retention (e.g., avoid prolonged exposure to strong protic acids/bases when N–D preservation matters).

Target Specificity

Not applicable. This product is a small-molecule deuterated aniline, not an antibody, enzyme, or affinity reagent.

• Item-specific: No target, epitope, clone, or species reactivity information is provided or relevant for this compound.

Perguntas frequentes

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. 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 1071170-27-8, the molecular formula is C8H5D6N, and the molecular weight is 127.22 g/mol.

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.