Dimethyl-d6 carbonate - ≥98%,≥99 atom% D , CAS No.108481-44-3

CAS: 108481-44-3 Cat. No.: D302175 Formule: C₃D₆O₃ Poids moléculaire: 96.11 Numéro CE: 690-550-3

GRADE & PURITY ≥98%,≥99 atom% D

Synonyms

AMY37005 | DIMETHYL CARBONATE-D6-D | Dimethylcarbonate-d6 | Dimethyl-d6 carbonate | Dimethylcarbona | Dimethyl-d6 carbonate, 99 atom % D, 97% (CP) | Bis[(~2~H_3_)methyl] carbonate | DTXSID90679845 | F90789 | MFCD01073488 | AKOS015910282 | bis(trideuteriom

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Specifications

Synonymes

AMY37005 | DIMETHYL CARBONATE-D6-D | Dimethylcarbonate-d6 | Dimethyl-d6 carbonate | Dimethylcarbona | Dimethyl-d6 carbonate, 99 atom % D, 97% (CP) | Bis[(~2~H_3_)methyl] carbonate | DTXSID90679845 | F90789 | MFCD01073488 | AKOS015910282 | bis(trideuteriom

Spécifications et pureté

≥98%,≥99 atom% D

Conditions de stockage de stockage

Store at 2-8°C,Protected from light,Desiccated

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Pureté

≥98%,≥99 atom% D

Noms et identifiants

Sourires canoniques

COC(=O)OC

IUPAC Name

bis(trideuteriomethyl) carbonate

InChIKey

IEJIGPNLZYLLBP-WFGJKAKNSA-N

INCHI

1S/C3H6O3/c1-5-3(4)6-2/h1-2H3/i1D3,2D3

Isomères SMILES

[2H]C([2H])([2H])OC(=O)OC([2H])([2H])[2H]

CAS alternatif

616-38-6（unlabelled）

Numéro ONU

UN 1161

Groupe d'emballage

II

Poids moléculaire

96.11

Reaxy-Rn

635821

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=635821&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Organic carbonic acids and derivatives
      • Subclass Carbonic acid diesters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Organic carbonic acids and derivatives
• Subclass: Carbonic acid diesters
• Intermediate Tree Nodes: Not available
• Direct Parent: Carbonic acid diesters
• Alternative Parents: Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Carbonic acid diester - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as carbonic acid diesters. These are compounds comprising the carbonic acid diester functional group.
• 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

Propriétés chimiques et physiques

• Point d'éclair (°F): 60.8 °F
• Point d'éclair (°C): 16 °C
• Point d'ébullition (°C): 90 °C
• Point de fusion (°C): 2-4 °C
• Poids moléculaire: 96.110 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 96.0694 Da
• Monoisotopic Mass: 96.0694 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 44.000
• Isotope Atom Count: 6
• 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 antibody/assay protocols are associated with this reagent. For synthetic use, see Reaction Conditions and Synthetic Utility for literature‑based procedures and optimization tips.

Analytical suggestions (general):

• Internal standards: When products labeled via dimethyl‑d6 carbonate are used as LC–MS/GC–MS internal standards, prepare calibration curves spanning expected analyte levels; verify co‑elution and response factors.
• NMR: For 1H NMR of labeled products, confirm suppression of O‑CH3 signals; acquire 2H NMR to quantify deuteration. Choose an appropriate lock solvent (e.g., CDCl3, DMSO‑d6) since DMC‑d6 is not a standard lock solvent.
• Purification: Carbonate‑based reactions often allow straightforward evaporation; employ silica gel chromatography with non‑protic eluents (e.g., hexanes/EtOAc or toluene/EtOAc). Avoid acidic stationary phases if carbamates/carbonates are present.

Always consult the product’s SDS and CoA for handling and quality details specific to this item.

Biological Roles

This product is a small organic carbonate used for chemical synthesis and analytical labeling. No endogenous biological role is associated with dimethyl carbonate or its deuterated analog.

Relevant notes (general/literature):

• Metabolic fate: Simple carbonates can hydrolyze to alcohols and CO2 under enzymatic or chemical conditions, but dimethyl carbonate is not a native metabolite and is not known to participate in primary biochemical pathways.
• Analytical biochemistry use: The deuterated isotopologue (dimethyl‑d6 carbonate) is valuable for preparing deuterium‑labeled internal standards (e.g., O‑CD3 ethers, carbamates) used in quantitative LC–MS/GC–MS assays to correct for matrix effects and ionization variability.
• Spectroscopy: Deuteration shifts vibrational frequencies and simplifies 1H NMR backgrounds, aiding mechanistic, kinetic isotope effect, and surface/interface studies (e.g., in battery electrolyte research or model membranes), but these are research utilities rather than biological functions.

Compliance note: This product is designated “For research use only” (per Product Data). It is not intended for diagnostic, therapeutic, or clinical applications.

If using labeled standards in bioanalytical workflows, verify isotopic purity, absence of exchangeable deuterium in the targeted moiety under assay conditions, and lack of interfering impurities. Validate stability in sample preparation steps (e.g., pH, temperature, and solvent exposure) to avoid back‑exchange or hydrolysis of carbonate/ether linkages.

Buffer Applications

Dimethyl‑d6 carbonate is not a buffering agent and is not typically used to formulate aqueous biological buffers. It lacks acid/base functionality in the physiological pH range and exhibits only limited water miscibility.

Practical guidance:

• If present in aqueous systems, it is generally as a co‑solvent or extractant rather than as a buffer component. Assess phase behavior and potential hydrolysis under basic or acidic aqueous conditions.
• For applications requiring pH control, select established buffer systems (e.g., phosphate, HEPES, Tris) and consider DMC‑d6 only as an organic phase/reagent for isotopic labeling prior to aqueous workup.

Refer to other sections (Reaction & Applications; Synthetic Utility) for relevant, non‑buffer uses of this reagent.

Green Alternatives

Dimethyl carbonate is widely cited as a green reagent/solvent relative to traditional alkylating agents and chlorinated solvents. The deuterated isotopologue retains these advantages for isotopic labeling campaigns. Literature comparison (qualitative):

• Environmental/health profile:
  • DMC (and DMC‑d6) is non‑halogenated, biodegradable, and exhibits comparatively low acute toxicity versus methyl halides and dialkyl sulfates. Byproducts are often methanol and CO2.
• Process benefits:
  • Reduced waste and corrosivity versus CD3I or CD3OTf; easier handling and lower PPE burden (still flammable—use standard solvent precautions).
• Tradeoffs:
  • Typically requires higher temperature, longer reaction times, and/or stronger base to achieve comparable conversions to methyl iodide/triflate.
  • Selectivity management is needed to favor O‑ vs N‑ or S‑alkylation depending on substrate and conditions.

Compact comparison (literature):

• CD3I: High reactivity; hazardous (toxic/volatile/iodide waste); good for low‑temp alkylation; expensive and regulated in some locales.
• CD3OTf: Extremely reactive; moisture sensitive; generates strong acid byproducts; specialized handling.
• Dimethyl‑d6 carbonate: Greener, non‑halogenated; benign byproducts; moderate reactivity; flammable, base‑sensitive; broadly compatible with organocatalysis.

Greener process suggestions:

• Use DMC‑d6 as both reagent and solvent to minimize solvent inventory; apply catalytic bases (DBU, TBD) or carbonate salts.
• Employ continuous removal of methanol or use CO2 pressure management to drive equilibria.
• Consider recyclable heterogeneous bases (hydrotalcites) and lower‑temperature microwave protocols reported in the literature.

Pharmaceutical Uses

No pharmacopeial status or excipient designation is specified for this item. Dimethyl‑d6 carbonate is supplied for research use only.

General, non‑clinical context (literature/industry practice):

• Process solvent/reagent: Non‑deuterated dimethyl carbonate has seen use as a greener process solvent and as a methylating/carbonylating reagent in synthesis of intermediates. The deuterated isotopologue can analogously be used in process development for isotopically labeled intermediates/standards.
• Isotopically labeled standards: D‑labeled ethers/carbamates prepared from dimethyl‑d6 carbonate are often employed as internal standards in LC–MS/GC–MS methods supporting pharmaceutical development (e.g., impurity profiling, metabolism studies), due to co‑elution and similar ionization behavior, without making any therapeutic claims.
• Extractables/leachables studies: Deuterated analogs can aid in tracing solvent origins or deconvoluting background signals in packaging studies, though DMC‑d6 itself is more commonly a synthetic tool.

Caveats:

• Residual solvent considerations in drug substance/drug product development follow ICH Q3C; DMC (non‑deuterated) is typically a Class 3 solvent. Any use must be supported by process clearance data. Deuterated variants should be treated analogously with appropriate analytical controls.

Always verify suitability with internal quality systems; this product is not intended for clinical or GMP use unless specifically qualified.

Physical Properties

Item-specific measured specifications are not provided in the Product Data. The following values are typical for dimethyl carbonate and are expected to be essentially similar for dimethyl‑d6 carbonate (isotopic substitution minimally affects bulk properties). All values are literature/typical unless noted; consult the item’s CoA/SDS for authoritative data.

• State/appearance: Not specified for this item; refer to CoA/Spec Sheet. (DMC is typically a clear, colorless liquid.)
• Boiling point: ~90–91 °C at 1 atm (literature, dimethyl carbonate)
• Melting point: ~2–4 °C (literature)
• Density (20 °C): ~1.07 g/mL (literature)
• Refractive index nD20: ~1.368 (literature)
• Viscosity (25 °C): ~0.6–0.7 mPa·s (literature)
• Vapor pressure (25 °C): ~4–5 kPa (literature)
• Dielectric constant (25 °C): ~3.1 (literature)
• Solubility in water (20–25 °C): partially miscible; ca. 1.5–3 wt% in water; water in DMC up to ~14 wt% (literature, system dependent)
• LogP (octanol/water): approximately −0.5 to −0.4 (literature)
• Henry’s law/volatility: relatively volatile; readily removed under mild vacuum (general literature observation)
• pKa: Not applicable (no acidic protons); conjugate acid pKa of methoxy oxygen not typically defined (general chemistry)

Notes for deuterated material:

• Molecular weight (C3D6O3) ≈ 96.1 g/mol (literature/computed); normal DMC is 90.08 g/mol. The ~6 amu increase has negligible impact on macroscopic properties within routine lab precision.
• Spectroscopy: Deuterium substitution suppresses 1H signals on the methyl groups; 2H NMR shows a characteristic singlet for CD3.

Quality and Grades

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

Interpretation and guidance (general):

• When a grade is unspecified for an isotopically labeled solvent/reagent like dimethyl‑d6 carbonate, users should verify isotopic enrichment (fractional deuteration of methyl groups), residual 1H content, water content, and common volatile/nonvolatile impurities on the Certificate of Analysis (CoA). These parameters strongly influence NMR/background performance and synthetic labeling fidelity.
• If an HPLC or LC–MS grade is offered for analogous carbonate solvents, it typically implies minimized UV‑absorbing and ionic impurities and low particulate levels—beneficial for trace analysis. For deuterated reagents, additional metrics such as 2H isotopic purity and 13C content may also be stated by some suppliers.
• Stabilizers: None are listed in the Product Data for this item. If a stabilizer is present in other suppliers’ materials (rare for DMC), it would be declared on the CoA; stabilizers can subtly affect reactivity in base‑catalyzed methylation/transesterification.
• Batch‑to‑batch control: For isotopic reagents, confirm lot‑specific data such as: %D incorporation (by 1H/2H NMR), water (Karl Fischer), residual methanol or dimethyl carbonate (protium) content, and GC area % purity.

Recommendation: For quantitative isotopic labeling or analytical internal standards, request the latest CoA/Spec Sheet to align isotopic enrichment and impurity profile with your application’s acceptance criteria.

Reaction and Applications

Dimethyl‑d6 carbonate serves as a dual‑role reagent: a solvent and a benign methylating/carbonylating agent that transfers trideuteriomethyl groups (–OCD3) under suitable conditions. The following are literature applications, expected to translate directly to the deuterated isotopologue:

• O‑Methylation (deuteromethylation) of phenols and alcohols:
  • Base‑catalyzed SN2 on the methyl carbon yields –OCD3 ethers with methoxide as leaving group and CO2 evolution in some pathways. Typical bases: K2CO3, Cs2CO3, NaOMe; phase‑transfer catalysts (TBAB) sometimes beneficial.
  • Advantages over CD3I/CD3OTf: Less toxic, non‑halogenated, generates benign byproducts; often requires higher temperatures or longer times.
• N‑Methylation/Carbamoylation of amines:
  • Reaction of amines with DMC‑d6 produces N‑carbamates (–NHCO2CD3) under milder conditions; with stronger bases/temperatures, direct N‑CD3 methylation can occur for certain substrates (BAl2 mechanism, literature). Useful for installing deuterated carbamate protecting groups or labels.
• S‑Methylation of thiols/thiophenols:
  • Forms thioethers (–SCD3) under basic conditions; often faster than O‑alkylation (soft nucleophiles favored).
• Transesterification/carbonate formation:
  • Diols react to give cyclic or linear carbonates incorporating –OCO2CD3 or carbonate linkages; catalyzed by organocatalysts (TBD, DBU) or metal catalysts.
• Isotopic labeling workflows:
  • Preparation of anisole‑d3 and related aryl‑OCD3 ethers for mechanistic probes, internal standards for GC/LC–MS, and vibrational spectroscopy studies (isotopic shifts).
• Electrolyte/solvent research:
  • Used as a model deuterated carbonate in battery electrolyte studies (spectroscopy, interfacial mechanisms), where deuteration aids vibrational/NMR analyses.

Practical notes: Remove water rigorously (molecular sieves, distillation); control basicity to bias O‑ vs N‑alkylation; consider sealed‑tube/pressure setups for CO2‑releasing variants; verify deuterium incorporation by 1H/2H NMR and MS.

Reaction Conditions

The following are representative, literature‑based conditions for dimethyl carbonate chemistry that apply analogously to dimethyl‑d6 carbonate. Optimize per substrate and verify deuterium incorporation.

• O‑Deuteromethylation of phenols/alcohols:
  • Conditions: K2CO3 (1.2–2.0 eq), DMC‑d6 as solvent/reagent (5–20 mL/g substrate), 90–120 °C (sealed tube or reflux if bp permits), 2–16 h.
  • Additives: TBAB (1–5 mol%) or DMAP (5–10 mol%) can accelerate sluggish substrates.
  • Outcomes: Typical literature yields 70–95% for activated phenols; aliphatic alcohols may require stronger bases (NaOMe/NaH) or longer times.
• N‑Carbamoylation of amines:
  • Conditions: DMC‑d6 (solvent/reagent), 60–100 °C, catalytic DBU/TBD or K2CO3 (0.1–0.5 eq), 2–12 h → R–NHCO2CD3.
  • For direct N‑CD3 alkylation (substrate‑dependent): stronger base (NaH, KOtBu) and 110–150 °C may be required; monitor for over‑alkylation.
• S‑Deuteromethylation of thiols:
  • Conditions: K2CO3 or Cs2CO3 (1–2 eq), DMC‑d6, 60–100 °C, 1–6 h; often high yields.
• Transesterification with diols (carbonate formation):
  • Catalysts: Organocatalysts (TBD, DBU), metal catalysts (Zn, Sn, Ti alkoxides), or heterogeneous bases (hydrotalcites).
  • Conditions: 80–140 °C; removal of methanol (or application of slight vacuum) to drive equilibrium; 2–24 h.

General advice:

• Water control is critical; dry glassware, sieves in situ, and inert atmosphere help maintain activity and isotopic integrity.
• Reaction monitoring: GC/MS to confirm +3 amu per CD3 incorporated vs CH3 analog; 1H NMR to verify loss of O–CH3 resonance and absence of back‑exchange.
• Workup: Quench bases carefully; avoid prolonged acidic aqueous exposure to minimize hydrolysis or H/D exchange at labile positions.

Safety and Handling

GHS classification, signal word, and H‑statements are not specified for this item in the Product Data. Always consult the SDS for authoritative hazard and precautionary information.

General safety considerations for carbonate solvents (literature/good practice):

• Likely hazards: Flammable liquid and vapor; may cause eye/skin irritation; inhalation of vapors may cause respiratory irritation and CNS effects at high concentrations.
• PPE: Use chemical‑resistant gloves (e.g., nitrile), safety goggles or face shield, lab coat. Employ splash protection if handling larger volumes.
• Engineering controls: Work in a fume hood to control vapors. Use explosion‑proof ventilation/equipment in areas with vapors.
• Handling: Keep away from heat, sparks, open flames, and hot surfaces. Ground/bond containers during transfer. Avoid breathing vapors/aerosols.
• Incompatibilities: Strong bases and nucleophiles can undergo transesterification/methylation; strong acids promote hydrolysis. Avoid strong oxidizers. Moisture can slowly hydrolyze carbonate; maintain dry conditions for sensitive applications.
• Peroxide formation: Not a peroxide‑forming ether; routine peroxide testing not typically required (general).
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Remove contaminated clothing; wash with soap and water.
  • Eye contact: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Spill/Fire response: Absorb small spills with inert material. For fires, use CO2, dry chemical, or alcohol‑resistant foam; water spray may be used to cool containers.

Storage per Product Data: Store at 2–8 °C, protected from light, desiccated. Ship on wet ice.

Solvent Selection

Dimethyl‑d6 carbonate (DMC‑d6) functions both as a polar aprotic solvent and as a deuterated methyl/carbonylating reagent. Selection guidance (general literature values for DMC):

• Polarity/parameters:
  • Dielectric constant ~3.1 (25 °C) → low‑to‑moderate polarity, similar to ethyl acetate; more polar than toluene, less than acetonitrile.
  • Donor/acceptor: Lewis basic at the carbonyl/alkoxy oxygens; no hydrogen‑bond donation.
  • Viscosity low (~0.6–0.7 mPa·s) → favorable mass transfer.
• Miscibility:
  • Miscible with many organics (ethers, esters, aromatics, chlorinated solvents).
  • Limited but notable water miscibility; phase behavior depends on composition and temperature.
• When to choose DMC‑d6:
  • As reaction medium for base‑catalyzed O‑, N‑, and S‑methylation/carbonylation where incorporation of –OCD3 (or carbamate formation) is desired.
  • As a low‑UV, relatively green solvent in place of dichloromethane, acetone, or acetonitrile for certain extractions and reactions—keeping in mind water compatibility and reactivity toward strong nucleophiles.
  • As an NMR sample diluent when suppression of 1H background from the solvent methyl groups is advantageous; note it is not a standard lock solvent.
• Comparison (literature, qualitative):
  • vs MeCN: DMC has lower polarity and higher bp; greener profile; poorer for highly polar solutes.
  • vs EtOAc: Similar polarity; DMC is more resistant to hydrolysis than simple esters under neutral conditions, but still transesterifies under base.
  • vs Carbonates (EMC/DEC): DMC is more volatile and polar; better for room‑temperature evaporation.

Note: For moisture‑sensitive work, dry over molecular sieves and maintain desiccated storage as per Product Data.

Storage and Reconstitution

• Storage conditions (item-specific, from Product Data): Store at 2–8 °C, protected from light, desiccated. Shipped on wet ice.
• Container: Keep tightly closed in an amber, air‑tight container. For moisture‑sensitive or long‑term storage, consider a septum‑sealed vial under inert gas (N2/Ar) with activated molecular sieves (3 Å) to maintain dryness.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Monitor for hydrolysis (methanol formation) or changes in GC purity.
• Reconstitution: Not applicable—supplied as a neat liquid reagent. If solidification occurs near its melting point, gently warm to ambient temperature with mixing to ensure homogeneity before use.
• Handling before use: Allow to equilibrate to room temperature in a closed container to avoid moisture condensation. If anhydrous conditions are critical, dispense via dry syringe/needle under inert atmosphere.
• Stability considerations: Avoid prolonged exposure to strong acids/bases that promote hydrolysis/transesterification. Protect from light as specified to minimize potential photolytic degradation.
• Quality checks: For isotopic applications, verify %D incorporation by 1H/2H NMR on receipt and after extended storage; assess water content by Karl Fischer if relevant to your process.

Note: Appearance, grade/purity, and additional specifications are not specified for this item; consult the lot‑specific CoA/Spec Sheet for details.

Structure and Identity

Dimethyl‑d6 carbonate is the fully deuterated isotopologue of dimethyl carbonate, featuring two trideuteriomethoxy groups bound to a central carbonyl carbon via carbonate linkages.

• Product name: Dimethyl‑d6 carbonate
• CAS: 108481-44-3 (item-specific)
• CID: 51341918 (item-specific)
• InChIKey: 138702 (as provided in Product Data); standard InChIKey not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet. A representative literature SMILES for the fully deuterated isotopologue is [2H]C([2H])([2H])OC(=O)O[2H]C([2H])[2H].
• Molecular formula: Literature (isotopologue): C3D6O3 (all non-exchangeable hydrogens replaced by deuterium). Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Literature (isotopologue, average): ~96.1 g/mol; item-specific value not specified; refer to CoA/Spec Sheet.

Structural features (general description):

• Functional groups: A symmetric, acyclic carbonate diester (–O–C(=O)–O–) connecting two trideuteriomethyl (–OCD3) substituents.
• Rings/stereochemistry: No rings; no stereocenters; planar carbonyl (sp2) with sp3 deuterated methyl groups.
• Polar character: Polar aprotic core from the carbonate; limited hydrogen bonding as donor, moderate as acceptor (carbonyl and alkoxy oxygens).

2D structure in words (general): A central carbonyl carbon double‑bonded to one oxygen and single‑bonded to two alkoxy oxygens. Each alkoxy oxygen is bound to a CD3 group (three deuteriums attached to a methyl carbon). The molecule is symmetric about the carbonyl carbon, giving two equivalent trideuteriomethoxy termini.

Synthetic Utility

Functional profile: Dimethyl‑d6 carbonate is a symmetric dialkyl carbonate capable of acting as a source of trideuteriomethyl (–CD3) and carbonyl (–CO2–) fragments. Its reactivity is governed by ambident electrophilicity at the methyl carbons (SN2) and at the carbonyl carbon (acyl substitution/transcarbonylation).

Key transformations (literature):

• O‑Deuteromethylation: Phenols/aliphatic alcohols → R–O–CD3 using base (K2CO3, Cs2CO3, NaOMe) in DMC‑d6 (often solvent and reagent). Competitive transesterification minimized by anhydrous conditions.
• N‑Carbamoylation and N‑Deuteromethylation: Primary/secondary amines → carbamates (R–NH–CO2–CD3); under stronger basic/thermal conditions, direct N‑CD3 alkylation may occur for less hindered amines.
• S‑Deuteromethylation: Thiols/thiophenols → thioethers (R–S–CD3), typically faster than O‑alkylation.
• Carbonate formation with diols: Production of linear/cyclic carbonates; enables incorporation of labeled carbonate linkages in oligomers/polymers.

Strategic uses:

• Installation of non‑exchangeable deuterium labels for MS quantitation (e.g., aryl‑OCD3 ethers) with improved safety/greenness compared to CD3I/CD3OTf.
• Protecting group chemistry: –CO2CD3 carbamates as removable N‑protecting groups (thermolabile or base‑cleavable pathways), providing an isotopically tagged handle.
• Retrosynthetic lever: DMC‑d6 can replace toxic alkylating agents in late‑stage functionalization when substrates tolerate basic/thermal conditions.

Operational tips:

• Drying: Employ 3 Å molecular sieves or distill from CaH2; store desiccated (per Product Data) to suppress hydrolysis.
• Selectivity: Control temperature and base strength to favor O‑ over N‑alkylation as required; phase‑transfer catalysis can enhance rates.
• Verification: Confirm deuterium incorporation by 1H NMR suppression, 2H NMR signal at ~3.7–3.8 ppm equivalent region (2H scale), and accurate mass shifts.

Target Specificity

Not applicable. This product is a small‑molecule carbonate reagent/solvent and is not a biological targeting agent, antibody, or probe. No target, epitope, clone, isotype, or species reactivity data are associated with this item.

Foire aux questions

How is this product shipped?

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