Benzylmethylether-d , CAS No.170464-05-8

CAS: 170464-05-8 Cat. No.: B1440026 Formula: C₈H₈D₂O Molecular Weight: 124.18

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Benzylmethylether-d2 (Methoxymethylbenzene-d2) is the deuterium labeled (Methoxymethyl)benzene.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

Molecular Weight

124.18

Application Protocols

Item-specific validated applications are not provided in the Product Data.

General guidance

• GC/LC-MS internal standard: Prepare stock solution at a defined concentration in a suitable solvent (e.g., acetonitrile, isooctane). Spike samples at a constant concentration across calibration and unknowns. Verify retention-time proximity and lack of interference.
• NMR reference/tracer: For 2H NMR, dissolve in a compatible deuterated solvent; acquire spectra with appropriate relaxation delays for quantitative work. For 1H NMR KIE studies, ensure that deuterium placement reduces overlapping proton signals or use MS readouts.

Please consult the CoA/SDS for any item-specific instructions.

Biological Roles

Applicability

• This product is intended for research use only. As a small-molecule organic ether, it has no established endogenous biological role.

General notes

• Deuterated small molecules are commonly used as internal standards in bioanalytical assays (e.g., plasma/urine quantitation) due to isotopic co-behavior and mass shift; suitability depends on analyte overlap and matrix effects.
• No biochemical pathway or metabolic role is implied for this material. Any use in biological systems should focus on analytical calibration or tracer studies under appropriate approvals.

Buffer Applications

Not typically applicable.

• As a neutral organic ether, this compound is not used as a buffering agent and has no defined acid/base pair suitable for buffering. For lab workflows, refer instead to the Reaction & Applications and Synthetic Utility sections for relevant usage.

Green Alternatives

Context

• This item is a deuterium-labeled specialty reagent. Green substitution is generally not applicable when isotopic labeling is required for mechanistic or analytical work.

General considerations (literature/guidance)

• If selecting an ether as a reaction solvent rather than using this compound as a labeled substrate/standard, consider greener ether solvents:

Comparison (general, not item-specific)

• 2-MeTHF: Biomass-derived option; higher boiling point than THF; lower miscibility with water; forms peroxides more slowly than diethyl ether.
• CPME: Broad solvent window, low peroxide formation tendency, good hydrophobicity, azeotrope behavior beneficial for water removal.
• MTBE: Lower toxicity compared to diethyl ether; relatively stable but still flammable; moderate polarity.

Trade-offs

• Greener ethers may differ in polarity, azeotrope formation, and workup profiles. For labeled mechanistic probes, no direct green alternative exists because the isotope placement is integral to the study.

Pharmaceutical Uses

Not typically applicable as a therapeutic or excipient specification.

• Deuterated organics like this are generally employed as analytical internal standards or mechanistic probes in R&D settings, not as formulated pharmaceutical excipients. No pharmacopeial monograph is indicated for this item. Any GMP-related use would require additional qualification and documentation not provided here.

Physical Properties

Item-specific facts (from Product Data)

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

Literature/computed values for the non-deuterated analogue (benzyl methyl ether; guidance only)

• Typical BP: ~170–172 °C (literature, parent compound)
• Typical MP: < −60 °C (literature, parent compound; liquid at ambient conditions)
• Density (20–25 °C): ~0.94–0.97 g/mL (literature, parent compound)
• Refractive index (nD20): ~1.50–1.52 (literature, parent compound)
• Solubility: Sparingly soluble in water; miscible with most organic solvents (literature, parent compound)
• LogP (estimated, parent compound): ~2–2.5 (literature/estimates)
• Deuteration typically causes negligible changes in bulk physical properties compared to the protiated analogue; values above are for orientation only, not item specifications.

Notes

• Definitive specifications (e.g., exact isotopic enrichment, residual solvents, assay) are not provided here. Consult the CoA/Spec Sheet for item-specific values.

Quality & Grades

Item-specific facts (from Product Data)

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

Context and guidance

• For isotopically labeled organics, key quality attributes generally include: isotopic enrichment and labeling pattern (e.g., d1/d2/d3), chemical purity, residual solvents, water content, stabilizers (if any), and trace metal content. None are specified here; please review the CoA for this lot.
• If offered as “NMR grade” or similar (not stated here), this typically implies low protonated impurities and low UV-absorbing contaminants. In absence of such designation, assume standard research grade.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If a stabilizer is present, it can affect certain reactions (e.g., Lewis-acid-mediated cleavages); pre-treatment or distillation may be required.
• Recommended verification on receipt: Inspect labeling pattern by 1H/2H NMR, GC-MS or LC-MS; check for any peroxide content if storage history is extended (per institutional SOPs).

Reaction & Applications

Item-specific facts (from Product Data)

• Manufacturer Applications: Not specified.

General/literature applications for deuterated benzyl methyl ether analogues

• Isotopic tracer: Useful in mechanistic studies of ether cleavage (e.g., hydrogenolysis over Pd/C), benzylic activation, and oxidative pathways. Deuterium placement enables tracking of bond scission and hydrogen transfer events via MS and NMR.
• Internal/response standard: Can serve as a deuterated internal standard in GC-MS/LC-MS quantitation for benzyl ethers or related volatiles, provided co-elution and ionization characteristics are suitable.
• Probe in Lewis-acid-mediated cleavages: Reactions with strong acids or Lewis acids (e.g., BCl3, AlCl3 systems) can cleave benzyl–O or methyl–O bonds; isotopic labeling helps assign pathways and intermediates.
• Radical/photoredox contexts: As a substrate in benzylic C–O activation studies, deuteration can clarify hydrogen atom transfer versus SN1/SN2 mechanisms.

Practical tips

• Confirm labeling pattern (methyl-d3 vs benzylic-d2, etc.) before experimental design.
• Handle under inert gas if long-term storage is expected; minimize light/air exposure to limit any peroxide formation.
• For analytical use, prepare calibration solutions gravimetrically; verify isotopic purity by HRMS and 2H NMR.

Reaction Conditions

General guidance from literature (parent scaffold; not item-specific specifications)

• Hydrogenolysis: Pd/C (5–10 wt% relative to substrate), 1–3 bar H2, solvents such as EtOAc, EtOH, or hexanes/EtOAc mixtures, 20–40 °C, 1–12 h. Monitor by GC or NMR. Benzylic ethers typically cleave under mild conditions.
• Lewis-acid cleavage: BCl3 or AlCl3 in dichloromethane or toluene at −78 to 25 °C; quench carefully. Selectivity for benzyl–O vs methyl–O cleavage may depend on conditions and substrate substitution.
• Radical/photoredox activation: Photocatalysts (e.g., Ir-based) under blue light can induce benzylic C–O activation in the presence of hydrogen atom donors; conditions vary widely with catalyst and substrate.

Analytical use

• As an internal standard, prepare calibration levels gravimetrically. Use dry, oxygen-free solvents to minimize isotope exchange or oxidative byproducts; store working solutions cold and protected from light.

Notes

• The exact deuterium placement dictates susceptibility to exchange. Avoid strong acids/bases and protic media when preservation of deuterium at benzylic or methyl positions is required.

Safety & Handling

Item-specific facts (from Product Data)

• GHS classification, pictograms, H-statements, signal word: Not specified for this item; refer to SDS.
• Storage: Store at −20 °C. Shipments are sent cold (ice chest + ice pads) to maintain material integrity.

General safety considerations (literature/good practice)

• Ethers can be flammable and may form peroxides upon prolonged exposure to air and light. Although benzyl ethers are typically less peroxide-prone than dialkyl ethers, periodic testing and proper storage under inert atmosphere and low temperature are prudent.
• Incompatibilities: Strong oxidizers, strong acids or Lewis acids (which may promote cleavage), and reactive metals. Avoid heating near ignition sources.
• PPE: Use lab coat, safety glasses, and appropriate solvent-resistant gloves. Work in a fume hood to avoid inhalation of vapors.
• First-aid overview: Inhalation—move to fresh air; Skin—wash with soap/water; Eyes—rinse with water for several minutes; Ingestion—rinse mouth, do not induce vomiting; seek medical attention as per SDS guidance.
• Waste: Collect organic ether waste in compatible containers; add peroxide quench procedures if needed per institutional policy.

Always consult the product-specific SDS for authoritative hazard, exposure limits, and emergency measures.

Solvent Selection

Applicability

• This product is an isotopically labeled organic ether. It is typically used as a labeled reagent/standard rather than chosen as a bulk reaction solvent.

General solvent-related characteristics (literature, parent scaffold)

• Polarity: Nonpolar to weakly polar, aprotic ether; low dielectric constant relative to polar aprotic solvents.
• Miscibility: Generally miscible with many organic solvents (e.g., hexanes, toluene, ethers, chlorinated solvents); sparingly soluble in water.

When to use

• As an isotopic standard in GC/LC-MS or NMR method development and quantification.
• As a mechanistic probe where kinetic isotope effects at the methyl or benzylic position are desired. The exact applicability depends on the labeling pattern—verify on the CoA.

Alternatives

• For bulk ether solvent roles, consider MTBE, THF, 2-MeTHF, CPME, diethyl ether, or toluene depending on solvation needs and safety constraints. Select based on polarity, peroxide tendencies, and process requirements.

Storage & Reconstitution

Item-specific facts (from Product Data)

• Storage: Store at −20 °C.
• Shipping: Ice chest with ice pads to maintain cold chain.

General handling guidance

• Keep tightly closed under inert gas (nitrogen or argon) to minimize moisture/oxygen exposure. Protect from light.
• If supplied neat: Use dry, peroxide-free solvents for dilutions. For long-term stock solutions, store in sealed amber vials at −20 °C.
• Thawing: Allow to warm to room temperature before opening to prevent condensation ingress. Mix thoroughly before aliquoting.
• Peroxide precautions: For ethers stored long-term, consider periodic testing per institutional SOPs.

Reconstitution

• If supplied as a solution or requires dissolution, use anhydrous organic solvents (e.g., hexane, toluene, dichloromethane, acetonitrile) compatible with your application. Concentration and solvent choice should be guided by the CoA and experimental needs.

Research use

• For research use only, as stated in the Product Data.

Structure & Identity

Item-specific facts (from Product Data)

• Product name: Benzylmethylether-d (SKU: B1440026)
• CAS: 170464-05-8
• Storage conditions: Store at -20°C
• Shipped in: Ice chest + ice pads
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

General chemistry/literature context

• The name suggests a deuterium-labeled analogue of benzyl methyl ether (commonly written as PhCH2–O–CH3 for the non-deuterated parent). The exact location/extent of deuteration (e.g., methyl-d3, benzylic-d2, ring-d5) is not specified in the provided data and should be confirmed on the CoA.
• Structural features of the parent scaffold: one ether linkage connecting a benzyl moiety to an alkoxy group; aromatic ring; benzylic methylene; no inherent stereocenters.
• 2D description of the parent scaffold: an anisyl-like ether where an sp3 benzylic carbon (attached to phenyl) is bonded to oxygen, which is in turn bonded to a small alkyl group (methyl). Deuteration does not alter connectivity but replaces one or more hydrogens with deuterium for isotopic tracing or NMR purposes.

Synthetic Utility

General/literature context

• Functional motif: A benzyl–alkyl ether scaffold. While benzyl methyl ether itself is not a common protecting group reagent, it is a useful substrate for studying ether cleavage selectivity and benzylic activation.
• Isotopic labeling utility: Placement of deuterium enables kinetic isotope effect (KIE) measurements and mechanistic discrimination between SN1, SN2, and radical pathways in C–O bond activation.

Representative transformations (literature)

• Hydrogenolysis: Benzylic C–O cleavage over Pd/C under H2 to generate toluene (from benzyl fragment) and methanol from the alkoxy side; deuterium tracing clarifies hydrogen incorporation sites.
• Lewis acid cleavage: Strong Lewis acids (e.g., BCl3, AlCl3) or Brønsted acids can promote selective cleavage of benzyl–O or methyl–O bonds; isotope distribution in products identifies pathway.
• Oxidation: Benzylic oxidation (e.g., with DDQ, MnO2) can transform the benzyl fragment to the corresponding carbonyl; isotope tracking can reveal hydride vs hydrogen atom transfer events.

Practical notes

• Verify the deuterium location before drawing mechanistic conclusions.
• Avoid protic workups if preservation of deuterium at exchangeable positions is critical.

Target Specificity

Not applicable.

• This product is a small-molecule reagent, not a biological targeting agent. No antigen, epitope, or species reactivity information applies.

Frequently Asked Questions

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 170464-05-8, the molecular formula is C8H8D2O, and the molecular weight is 124.18 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.