1,1-Dimethoxy-3-(methylthio)propane - ≥95% , CAS No.13214-29-4

CAS: 13214-29-4 Cat. No.: D1001319 Summenformel: C₆H₁₄O₂S Molekulargewicht: 150.240 EG-Nummer: EINECS236-184-6

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

COC(CCSC)OC

IUPAC Name

1,1-dimethoxy-3-methylsulfanylpropane

InChIKey

BNYOSIKNPOOYIQ-UHFFFAOYSA-N

INCHI

1S/C6H14O2S/c1-7-6(8-2)4-5-9-3/h6H,4-5H2,1-3H3

Molekulargewicht

150.240

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Klasse Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Klasse: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Acetals
• Alternative Parents: Sulfenyl compounds Dialkylthioethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkylthioether - Sulfenyl compound - Thioether - Acetal - Hydrocarbon derivative - Organosulfur compound - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as acetals. These are compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 150.240 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 150.071 Da
• Monoisotopic Mass: 150.071 Da
• Topological Polar Surface Area: 43.800 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 55.000
• Isotope Atom Count: 0
• 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

Not applicable as standardized bioassay protocols (e.g., WB, IHC, IF, FC) do not pertain to this small-molecule building block. For practical synthetic protocols, see the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections.

Biological Roles

This compound is a synthetic organic intermediate and is not known as a natural metabolite or biological cofactor.

• General context (literature/general)

  • Acetals of aliphatic aldehydes are common protecting groups in organic synthesis and have no intrinsic biological signaling roles.
  • Simple thioethers can interact with proteins as soft ligands, but this specific structure is not associated with defined biochemical pathways.

• Research use note (from Product Data)

  • For research use only.

If biological testing is planned (e.g., as a chemical probe precursor), appropriate in vitro/in vivo safety assessments and regulatory approvals are required; no biological activity or targets are implied by this listing.

Buffer Applications

Not typically applicable. 1,1-Dimethoxy-3-(methylthio)propane is a hydrophobic organic building block, not a buffering agent. For experimental work involving this reagent, select buffer systems only if needed for biphasic or aqueous quench steps; otherwise, refer to the Solvent Selection and Reaction & Applications sections for relevant guidance.

Green Alternatives

Greenness considerations relate to the transformations you plan rather than the molecule itself. The acetal protects an aldehyde, enabling fewer protecting-group swaps and minimizing waste if chosen judiciously.

• Strategy-level alternatives (literature/general)

  • Use catalytic, recoverable acids (e.g., solid acids, sulfonated resins) for hydrolysis/transacetalization to reduce aqueous acidic waste.
  • Choose greener oxidants for S-oxidation (e.g., H2O2 with catalytic tungstate or acetic acid) over halogenated peracids when possible.
  • Favor bio-based solvents (2-MeTHF, CPME, EtOAc, MeTHF/toluene blends) instead of chlorinated solvents where compatible with rate/selectivity.

• Comparison (general guidance) | Goal | Conventional choice | Greener alternative | Trade-offs | |---|---|---|---| | Acetal hydrolysis | DCM or MeCN with mineral acid | EtOAc/MeOH/H2O or 2-MeTHF/H2O with catalytic organic acid | May require higher temperature/longer time | | Thioether → sulfoxide | m-CPBA in DCM | H2O2 in AcOH/EtOH or aqueous urea–H2O2 | Selectivity control needed to avoid over-oxidation | | Workup/drying | Na2SO4, MgSO4 | Brine minimization; solvent swap to lower-VOC options | Process optimization required |

• Waste and odor control

  • Sulfur-containing organics can cause odor nuisances at trace levels; ensure closed handling, activated carbon off-gas treatment, and segregated waste streams.

Pharmaceutical Uses

No pharmacopoeial monograph or excipient role is provided for this item.

• General context (literature/general)

  • Such bifunctional intermediates may serve as building blocks during API and intermediate synthesis (e.g., masked aldehyde strategies, sulfur-function manipulation), but they are not used as finished dosage excipients.
  • If used in GMP settings, specifications must be established (identity, purity, residual solvents, elemental impurities) and changes to the protecting group strategy justified in the control strategy.

• Compliance note

  • This product is supplied for research and laboratory use only. It is not intended for human or veterinary use, nor for incorporation into drug products without appropriate qualification and regulatory oversight.

Physical Properties

Item-specific specifications are not provided in the Product Data.

• Item-specific values

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, refractive index, water/peroxide/UV-cutoff, metal content: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general expectations (for context only; not product specifications)

  • Physical state: typically a low-viscosity, colorless to pale liquid for C6 acetals/thioethers.
  • Volatility: moderate; acetals are generally lower-boiling than analogous alcohols, while thioethers elevate boiling points vs ethers of similar carbon count.
  • Solubility: miscible with common organic solvents (e.g., ethers, chlorinated solvents, aromatics); expected low solubility in water due to hydrophobic chain and acetal functionality.
  • Acetal stability: stable under neutral/basic conditions; acid-catalyzed hydrolysis in the presence of water regenerates 3-(methylthio)propanal.

• Computed/literature identifiers

  • Molecular formula: C6H14O2S (literature/computed)
  • Molecular weight: ~150.24 g/mol (literature/computed)

Note: For definitive physical constants and acceptance criteria for this specific lot, consult the product’s CoA/Specification Sheet.

Quality and Grades

• Item-specific grade/purity information

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

• Guidance on interpreting grades (general)

  • Research-grade material is suitable for synthetic and analytical laboratory use but may not include low-UV or metal content guarantees unless explicitly stated.
  • HPLC/LC-MS grade designations (if present on a CoA) imply low background absorbance/ionizable impurities for trace analysis.
  • “≥99%” or similar assay values (if present) define compositional purity by GC/GC–MS/1H NMR; review impurity profiles (e.g., hydrolysis products, over-oxidized sulfur species) where reported.

• Stabilizers/inhibitors

  • No stabilizer is listed in the Product Data for this item. If present on the CoA, stabilizers can affect downstream reactions (especially acid-catalyzed steps) and may require removal (e.g., by distillation or short silica plug) prior to use.

• What to check on receipt

  • Verify appearance (typically clear, low-color liquid; any turbidity may indicate moisture uptake/hydrolysis). Confirm identity by GC–MS/NMR as needed.
  • Review water content and residual solvents on the CoA if provided; acetal performance in moisture-sensitive routes depends on dryness.

Reaction and Applications

This reagent merges an acid-labile aldehyde equivalent with a latent/transformable thioether, making it valuable in modular synthesis and linker design.

• Acetal as aldehyde protecting group (literature/general)

  • Under mild acid and water/alcohol, the dimethyl acetal hydrolyzes to 3-(methylthio)propanal. Choice of acid (e.g., PPTS, CSA, catalytic H2SO4) and solvent polarity governs rate/selectivity; anhydrous alcohols lead to transacetalization.
  • Practical tip: monitor by GC or 1H NMR (acetal methoxy singlets ~3.3–3.5 ppm disappear; aldehyde proton appears ~9–10 ppm).

• Thioether handle transformations (literature/general)

  • Chemoselective oxidation: S→O using m-CPBA or H2O2 to the sulfoxide (1 equiv oxidant, 0–5 C) or further to sulfone (2 equiv, room temp). Sulfones can act as robust electron-withdrawing groups for Julia-type reactions or as leaving groups after α-deprotonation.
  • Pummerer and related chemistry: pre-oxidation to sulfoxide followed by acylation can trigger Pummerer rearrangements to generate α-substituted sulfides.
  • Sulfonium salt formation: quaternization with alkyl halides or triflates generates sulfonium species that serve as activated leaving groups in subsequent substitutions or eliminations.

• Linker and conjugation utility (literature/general)

  • The 3-carbon spacer offers a defined distance between an aldehyde (after deprotection) and the sulfur functionality, useful in preparing bifunctional intermediates, odorant analogues, or surface modifiers after further derivatization.

• Compatibility and orthogonality

  • The acetal withstands many basic/nucleophilic steps that engage sulfur (e.g., S-alkylation, S-oxidation under controlled conditions), enabling stepwise assembly prior to final deprotection.

• Workup tips

  • Thoroughly remove acids post-hydrolysis to avoid overreaction; neutralize and dry organic layers to suppress re-acetalization or sulfur oxidation during concentration.

Reaction Conditions

The following are general literature-guidance conditions for common transformations of dimethyl acetals and alkyl thioethers. They are not specifications for this item.

• Acidic hydrolysis (acetal → aldehyde)

  • Typical: 0.5–5 mol% acid catalyst (PPTS, CSA, TsOH) in MeCN/H2O, THF/H2O, or acetone/H2O at 20–50 C; reaction times 0.5–6 h depending on acid strength and water content.
  • Workup: neutralize with NaHCO3, extract with EtOAc or DCM, dry, and minimize exposure to acid during concentration to prevent side reactions.

• Transacetalization (exchange of –OMe with alcohol solvent)

  • Use the desired ROH as solvent with catalytic acid (1–10 mol%); azeotropic removal of MeOH (Dean–Stark for higher-boiling alcohols) drives equilibrium.

• Thioether oxidation

  • To sulfoxide: 1.0–1.1 equiv m-CPBA (0–5 C) in DCM, 0.5–2 h; or 30% H2O2 (1.1 equiv) in AcOH at 0–25 C, monitoring to avoid over-oxidation.
  • To sulfone: 2.0–2.5 equiv oxidant at 20–40 C; solvents DCM, MeOH, or AcOH; times 1–6 h.

• Sulfonium salt formation (activation at sulfur)

  • Thioether + alkyl halide/triflate (1.2–2.0 equiv) in MeCN or DCM, room temperature to reflux, often with weak base scavenger; isolation by crystallization or aqueous workup.

• Compatibility notes

  • Maintain near-neutral conditions to preserve the acetal during sulfur chemistry. For metal-catalyzed steps, be aware sulfur can poison catalysts; protect/oxidize sulfur or use excess catalyst/poisons scavengers as needed.

Safety and Handling

Always handle in accordance with your institutional safety program and consult the SDS for authoritative information.

• Item-specific GHS data (from Product Data)

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.

• General hazards for acetals and thioethers (literature/general)

  • Combustible organic liquid; vapors may form flammable mixtures with air—keep away from ignition sources.
  • Thioethers often have strong odors and can cause irritation; avoid inhalation of vapors and skin contact.
  • Reactivity: acetal moiety is acid-labile; avoid contact with strong acids in the presence of moisture to prevent hydrolysis. Thioethers are susceptible to oxidation by strong oxidizers (→ sulfoxides/sulfones).

• Recommended PPE and handling practices (general)

  • Wear safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to control vapors/odors.
  • Segregate from strong acids and oxidizing agents. Keep containers tightly closed to minimize moisture ingress and odor.
  • First aid (overview): move to fresh air if inhaled; rinse skin with soap and water upon contact; flush eyes with water for several minutes and seek medical attention if irritation persists; if swallowed, do not induce vomiting—seek medical attention.

• Waste disposal

  • Collect organic liquid waste according to local regulations. Avoid release to the environment; sulfur-containing organics may be malodorous at trace levels.

Solvent Selection

This product is a functionalized building block rather than a routine reaction solvent. Solvent selection should therefore focus on the intended transformation of the acetal and/or thioether moieties.

• General solubility/miscibility (literature/general)

  • Expected to dissolve readily in nonpolar to moderately polar organic solvents: hexanes, toluene, MTBE/Et2O, THF/2-MeTHF, DCM/DCE, acetonitrile.
  • Limited water solubility is expected; biphasic conditions are common for acid-catalyzed hydrolysis if aqueous acid is used.

• Choosing solvents by transformation (general guidance)

  • Acetal hydrolysis: mixed solvent systems (THF/H2O, MeCN/H2O, acetone/H2O) with catalytic mineral or organic acids; avoid strongly nucleophilic alcohols if you wish to form the parent aldehyde selectively.
  • Oxidation of thioether: DCM, MeOH, EtOAc, or AcOH commonly used with Oxone, m-CPBA, H2O2/AcOH, or peracids; control stoichiometry and temperature to stop at sulfoxide or proceed to sulfone.
  • Formation of sulfonium salts or alkylation at sulfur: polar aprotic solvents (MeCN, DCM, DMF) with alkyl halides/triflates.
  • Subsequent aldehyde chemistry after deprotection: choose solvent per transformation (e.g., THF for Grignard additions to the revealed aldehyde; toluene for Knoevenagel condensations).

• Comparison note

  • Relative to unprotected 3-(methylthio)propanal, this acetal is more compatible with basic/neutral media and water-free conditions, enabling multistep sequences without aldehyde side reactions.

Storage and Reconstitution

• Item-specific storage/shipping

  • Storage conditions: Room temperature (per Product Data). Store in a cool, dry place in a tightly closed container.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Practical storage guidance (general)

  • Protect from strong acids and moisture to prevent acetal hydrolysis. Use dry inert atmosphere (e.g., nitrogen/argon) for long-term storage if frequently opened.
  • Keep away from oxidizing agents to avoid thioether oxidation during storage.
  • If moisture exposure is suspected, analyze by 1H NMR/GC for formation of 3-(methylthio)propanal or transacetalization products; purify by distillation or silica if necessary.

• Reconstitution/use

  • Material is supplied neat; no reconstitution is required. If weighing is impractical due to volatility, use gas-tight syringes to dispense by volume and correct with density from the CoA (if provided).

• Stability considerations

  • Under neutral, dry conditions, acetals are typically stable for extended periods. Avoid prolonged exposure to acids, oxidants, or elevated temperatures. Always refer to the lot-specific CoA/SDS for definitive guidance.

Structure and Identity

A bifunctional small-molecule building block combining a dimethyl acetal (masked aldehyde) with a terminal methyl thioether separated by a three‑carbon spacer.

• Item-specific identifiers (from Product Data)

  • SKU: D1001319
  • Product name: 1,1-Dimethoxy-3-(methylthio)propane
  • CAS: 13214-29-4
  • PubChem CID: 83240
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed structural information (for reference only)

  • Functional groups: dimethyl acetal (–CH(OMe)2) at C1; thioether (–S–Me) at C3 of a propane chain.
  • 2D description: MeO–CH(OMe)–CH2–CH2–S–Me (no defined stereogenic centers; achiral as drawn).
  • Molecular formula (computed from name): C6H14O2S (literature/computed)
  • Molecular weight (computed): ~150.24 g/mol (literature/computed)
  • Example non-stereospecific SMILES (literature): COC(CCSC)OC

• Structural features of note

  • The dimethyl acetal masks an aldehyde equivalent; acid-labile and stable to many nucleophiles/bases.
  • The methyl thioether provides a soft nucleophile/ligand handle amenable to oxidation (→ sulfoxide/sulfone) or activation (e.g., sulfonium formation).

Synthetic Utility

• Dual-function platform

  • Aldehyde equivalent: The dimethyl acetal unmasking provides 3-(methylthio)propanal on demand for condensations (e.g., Knoevenagel), nucleophilic additions (e.g., organometallics), or reductive aminations, while remaining inert to many basic steps in earlier sequences.
  • Sulfur vector: The terminal methyl thioether can be diversified by oxidation (sulfoxide/sulfone), alkylation (sulfonium formation), or substitution after activation, enabling tuning of polarity and leaving-group ability.

• Retrosynthetic perspectives (literature/general)

  • As a linchpin, it enables late-stage introduction of aldehyde reactivity proximal to a sulfur substituent—useful for installing sulfur-containing side chains or for tethered intramolecular cyclizations after deprotection.
  • Oxidized derivatives (sulfone) allow α-deprotonation and coupling (e.g., Julia–Kocienski-type strategies once converted appropriately), expanding C–C bond-forming options.

• Protecting-group orthogonality

  • The acetal tolerates bases, many nucleophiles, and mild oxidants; scheduling acid-sensitive steps last preserves the protecting group until needed.

• Practical notes

  • Keep reactions anhydrous unless hydrolysis is intended. Following S-oxidation, carefully control acid exposure to avoid concurrent acetal cleavage. For sulfonium-mediated substitutions, choose non-nucleophilic solvents and bases to protect the acetal.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent or antibody. No antigen/epitope, species reactivity, clone, or isotype information applies.