Allyl Dimethyldithiocarbamate - ≥98% , CAS No.20821-66-3

CAS: 20821-66-3 Cat. No.: A151292 Formule: C₆H₁₁NS₂ Poids moléculaire: 161.28 Numéro CE: 678-105-1

GRADE & PURITY ≥98%

Synonyms

InChI=1/C6H11NS2/c1-4-5-9-6(8)7(2)3/h4H,1,5H2,2-3H3 | Carbamic acid, dimethyldithio-, allyl ester | FT-0693025 | DTXSID90292836 | S-Allyl-N,N-dimethyldithiocarbamate | N,N-DIMETHYL(PROP-2-EN-1-YLSULFANYL)CARBOTHIOAMIDE | AKOS015850781 | Allyl N,N-dimethyl

Storage

Room temperature

Shipped In

Normal

Specifications

Synonymes

InChI=1/C6H11NS2/c1-4-5-9-6(8)7(2)3/h4H,1,5H2,2-3H3 | Carbamic acid, dimethyldithio-, allyl ester | FT-0693025 | DTXSID90292836 | S-Allyl-N,N-dimethyldithiocarbamate | N,N-DIMETHYL(PROP-2-EN-1-YLSULFANYL)CARBOTHIOAMIDE | AKOS015850781 | Allyl N,N-dimethyl

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Pureté

≥98%

Noms et identifiants

Sourires canoniques

CN(C)C(=S)SCC=C

IUPAC Name

prop-2-enyl N,N-dimethylcarbamodithioate

InChIKey

ZFMLVJCASVPGIT-UHFFFAOYSA-N

INCHI

1S/C6H11NS2/c1-4-5-9-6(8)7(2)3/h4H,1,5H2,2-3H3

Isomères SMILES

CN(C)C(=S)SCC=C

Poids moléculaire

161.28

Reaxy-Rn

1753057

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1753057&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Dithiocarbamic acids and derivatives
      • Subclass Dithiocarbamic acid esters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Dithiocarbamic acids and derivatives
• Subclass: Dithiocarbamic acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Dithiocarbamic acid esters
• Alternative Parents: Allyl sulfur compounds Sulfenyl compounds Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dithiocarbamic acid ester - Allyl sulfur compound - Sulfenyl compound - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as dithiocarbamic acid esters. These are organosulfur compounds with the general formula R3SC(=S)N(R1)R2; R1-R2 = H or organyl group, R3 = organyl.
• 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

• Indice de réfraction: 1.6
• Point d'éclair (°C): 71 °C
• Point d'ébullition (°C): 108°C/5mmHg(lit.)
• Poids moléculaire: 161.300 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 161.033 Da
• Monoisotopic Mass: 161.033 Da
• Topological Polar Surface Area: 60.600 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 110.000
• 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

No item-specific, validated application protocols are provided for this listing.

General lab-use outlines (informational only; adjust to your scale and safety requirements):

• Metal scavenging test:
  • Dissolve the reagent (e.g., 5–20 mM) in DCM; contact with metal-containing aqueous phase (neutral pH). Shake, separate, and assay metal content by ICP.
• Radical addition trial:
  • Combine substrate and reagent in toluene with 1–2 mol% AIBN under N2; heat to 70 °C; monitor by TLC/GC-MS. Optimize initiator loading and time.
• Allyl manipulation screen:
  • Under inert gas, expose to a soft nucleophile (e.g., thiolate) in MeCN at 40–60 °C to probe S–allyl transfer; analyze by LC-MS.

These are starting points only; develop full SOPs and conduct appropriate hazard/risk assessments.

Biological Roles

• Item-specific biological/biochemical data: Not specified for this item; for research use only.

• General biochemical context for dithiocarbamates (informational; no medical claims):

  • Metal chelation: Dithiocarbamates bind transition metals (Cu(II), Ni(II), Zn(II)) via soft sulfur donors, forming stable chelates. This underpins their use as analytical derivatization ligands and metal staining/extraction aids.
  • Redox/thiol chemistry: The thiocarbonylthio functionality can engage in radical and thiol-exchange processes under appropriate conditions, allowing labeling or crosslinking strategies in biomolecule model systems.
  • Membrane affinity: The hydrophobic allyl–thioether moiety and overall lipophilicity suggest partitioning into organic phases or lipid environments, relevant for biphasic extraction protocols rather than in vivo use.

• Analytical/biochemical applications (lab-focused):

  • Potential as a derivatization agent for amines or alcohols (via interconversion routes) to improve chromatographic detection (e.g., UV/visible through thiocarbonyl absorbance) in method development.
  • Metal-sensing model systems: Formation of colored/UV-active metal–dithiocarbamate complexes can serve as simple proxies for monitoring metal availability in buffered organic/aqueous mixtures.

Note: This product is designated for research use only. No claims are made regarding biological activity, safety, or suitability for diagnostic/therapeutic applications.

Buffer Applications

This reagent is not a buffer component and is not typically used to control pH in aqueous systems.

• If used alongside buffers (general guidance):
  • Maintain aprotic organic phases or low-water content to minimize hydrolysis/oxidation.
  • If biphasic extractions with buffers are necessary (e.g., for metal capture), select buffers that avoid strong acidity/oxidants and verify partitioning behavior experimentally.

For pH-stable buffering needs, consider standard biological buffers (phosphate, Tris, HEPES); this reagent does not substitute for such systems.

Green Alternatives

Selection of greener strategies depends on the role of Allyl Dimethyldithiocarbamate in your process.

• If used as a sulfur-transfer/thiocarbonylthio reagent:
  • Consider xanthates or thiocarbonates derived from bio-based alcohols (e.g., 2-MeTHF-derived) when feasible; these can offer similar radical reactivity with potentially lower odor and improved handling.
• If used for metal capture/chelation:
  • Evaluate biobased chelants (e.g., polysaccharide-supported thiols, immobilized thioethers) for easier separation and reduced solvent use.
• If used in polymerization control (RAFT-like):
  • Alternative mediators such as trithiocarbonates may provide comparable control for certain monomers with different toxicity/odor profiles.

Greener solvent swaps (general guidance):

• Comparison (informational; not item-specific)
  • Conventional: DCM, toluene
  • Greener alternative: Ethyl acetate, 2-MeTHF, CPME
  • Trade-offs:
    • Ethyl acetate offers lower toxicity and good dissolving power but may promote hydrolysis in moist conditions.
    • 2-MeTHF/CPME are hydrophobic, support water-separations, and tolerate Grignard-like dryness; note peroxide formation risk for ethers—monitor and manage.

Process intensification:

• Use flow chemistry for radical additions to improve heat/mass transfer and reduce inventory of odorous intermediates.
• Apply solvent recycling and in-line metal scavenging to reduce waste.

Always validate reactivity/selectivity when substituting reagents; thiocarbonyl electronics differ among dithiocarbamates, xanthates, and trithiocarbonates.

Pharmaceutical Uses

No item-specific pharmacopeial status, excipient role, or GMP grade is provided for this listing.

• General note (non-clinical, research-only):

  • Dithiocarbamates are used in the lab as chelating ligands and derivatization agents; they are not standard pharmaceutical excipients.
  • If considering use in process development studies (e.g., metal scavenging in API synthesis), ensure comprehensive extractables/leachables and residual reagent controls, and confirm effective removal in downstream operations.

• Documentation to request for regulated environments:

  • Detailed CoA with assay/impurity profile.
  • Residual solvent data and potential nitrosamine risk assessment if secondary amines are present in process streams.
  • SDS and any available stability studies (temperature/light/moisture).

This product is supplied for research use only and is not intended for human or veterinary applications.

Physical Properties

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

• Literature/general properties for S-allyl N,N-dimethyldithiocarbamate (informational; not product specifications):

  • Physical state: typically a pale yellow to amber liquid or low-melting solid, with a characteristic sulfurous odor, consistent with many dithiocarbamate esters.
  • Approximate formula and mass: C6H11NS2; ~161.29 g/mol (literature).
  • Polarity/solubility: expected to be sparingly soluble in water and miscible with many organic solvents (e.g., dichloromethane, toluene, ethers, esters); the dialkylamino/thiocarbonyl motif provides moderate polarity and strong affinity for soft metals.
  • Volatility: moderate; handle under well-ventilated conditions to manage odor and potential vapor exposure.
  • Stability: dithiocarbamates can hydrolyze under strongly acidic conditions and oxidize in air/light; prefer storage away from acids, oxidants, and moisture.

• Properties commonly requested but not provided for this item:

  • Boiling point, melting point, density, refractive index, pKa, logP, UV cutoff, residuals/trace metals: Not specified for this item; refer to CoA/Spec Sheet.

Practical note (general): For exact chromatographic method development (e.g., GC/HPLC), determine sample-specific BP/RI or UV characteristics experimentally or consult the lot-specific CoA to avoid method transfer issues.

Quality and Grades

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

• How to interpret grades for this class of reagent (general guidance):

  • Reagent/AR grade emphasizes low inorganic contaminants and suitability for general synthesis.
  • High-purity or ≥98–99% assay grades are preferred for kinetic studies, polymerization mediators, or when trace impurities (e.g., amines, sulfur byproducts) could affect catalysis or analytical baselines.
  • GC/HPLC grade solvents/solutions of dithiocarbamates are uncommon; when chromatography is critical, verify UV-Vis and baseline behavior of the specific lot.

• Stabilizers/inhibitors:

  • Dithiocarbamates are sometimes shipped without stabilizers but benefit from controlled atmosphere (low O2, low light). Any stabilizers present would be disclosed on the CoA; otherwise assume none and store accordingly.

• What to look for on the CoA/Spec Sheet (practical checklist):

  • Assay method (e.g., 1H NMR qNMR, titration).
  • Identity confirmation (NMR, IR with characteristic C=S stretch ~1050–1200 cm−1; literature reference only), and MS consistent with ~161 Da (literature).
  • Residual solvents, acid/amine content, and peroxide/oxidation markers (where applicable).
  • Appearance limits (color, clarity) and water content if relevant to your application.

For regulated or trace-metal-sensitive work, request a detailed impurity profile and ensure batch-to-batch consistency.

Reaction and Applications

Allyl Dimethyldithiocarbamate is a versatile organosulfur building block combining an allylic thioether with a dithiocarbamate (thiocarbonyl) functionality.

Key reaction families and uses (literature/general):

• Ligand & scavenger for soft metals: Dithiocarbamates chelate Cu, Ni, Pd, and other soft/ borderline metals. Useful for metal capture from reaction mixtures or forming defined complexes for catalysis studies.
• Radical chemistry / RAFT paradigms: The dithiocarbamoyl group is a classical thiocarbonylthio motif used in reversible addition–fragmentation chain-transfer. Allyl groups can serve as R or transfer groups in radical additions; ensure oxygen-free conditions and appropriate initiator control.
• Thiofunctionalization & leaving-group strategies: The –S–allyl bond can engage in substitution or be leveraged in transition-metal-catalyzed allylic substitution (e.g., Pd-catalyzed Tsuji–Trost-type allylations from activated partners). The dithiocarbamate fragment can serve as a masked amine/sulfur donor or as a leaving group in transformations analogous to xanthate chemistry.
• Pericyclic/ionic rearrangements (analogy): Allyl sulfides and related thiocarbonyl systems are competent in [2,3]-sigmatropic rearrangements under appropriate activation, enabling C–S to C–C bond reorganization (substrate-dependent; literature precedent with allyl thioesters and xanthates).
• Protecting/derivatizing chemistry: Dithiocarbamate formation is a classical method to derivatize amines or alcohols (via interconversion to O-alkyl thiocarbamates/xanthates) for further manipulation (Barton–McCombie-type radical deoxygenation strategies employ related thiocarbonyls).

Practical tips:

• Work anhydrous and avoid acids/oxidants.
• Exclude O2 rigorously for radical applications.
• For metal-binding uses, adjust solvent polarity and pH (if biphasic) to optimize extraction and complexation.

Reaction Conditions

The following conditions are general literature-informed guidelines for dithiocarbamate/allyl-thioether chemistry and should be optimized empirically for your substrate set. They are not specifications for this item.

• Radical additions/fragmentations (thiocarbonylthio chemistry):

  • Solvents: toluene, dioxane, bulk monomer (for polymer-related work).
  • Initiation: AIBN (60–80 °C) or photoinitiation (blue/UV light) under O2-free conditions.
  • Typical times: 1–12 h thermally; minutes to hours photochemically depending on light flux.

• Metal complexation/extractions:

  • Solvents: DCM, CHCl3, toluene; optional biphasic water/organic with pH neutral to slightly basic.
  • Stoichiometry: ≥1–2 equiv relative to target metal; monitor by UV-Vis/LC or ICP of aqueous raffinate.

• Transition-metal-catalyzed allylic manipulation (conceptual):

  • Catalysts: Pd(0)/phosphine systems for allylic substitutions (when paired with suitable electrophiles or after activation/interconversion).
  • Solvents: THF, MeCN, toluene.
  • Temperatures: 20–80 °C; inert atmosphere.

• Nucleophilic substitution at sulfur (S–allyl cleavage):

  • Nucleophiles: thiolates, iodide, soft nucleophiles; polar aprotic solvents (DMF, DMSO, MeCN); 20–80 °C.

• Workup and purification:

  • Avoid strong acids/oxidants; quench with mild bases if needed.
  • Extract into nonpolar organics; purge odor by brief vacuum stripping at mild temperature; purify by column with basic modifier if tailing occurs.

Always confirm identity and purity by NMR/IR/MS; thiocarbonyl C=S typically shows strong IR bands in the 1050–1200 cm−1 range (literature reference).

Safety and Handling

• Item-specific hazard data (GHS, pictograms, H-statements): Not specified for this item; refer to the SDS for authoritative information.

• General hazards for dithiocarbamates (informational; not product-specific classification):

  • May cause skin/eye irritation and respiratory irritation. Characteristic sulfur odor; avoid inhalation of vapors.
  • Can chelate metal ions; avoid contact with copper and other soft metals if contamination is a concern.
  • Susceptible to oxidation; decomposition can release sulfur-containing fumes.

• Recommended PPE and engineering controls (good laboratory practice):

  • Nitrile gloves, lab coat, splash goggles; work in a fume hood.
  • Avoid open flames and ignition sources when handling bulk liquids.

• Incompatibilities and reactivity (general):

  • Strong acids (hydrolysis to amines/CS2 derivatives), strong oxidizers, and strong bases (can induce decomposition or rearrangement).
  • Prolonged exposure to air/light may promote oxidation; minimize headspace oxygen and light.

• First-aid overview (general guidance; defer to SDS):

  • Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical advice if irritation persists.
  • Inhalation: move to fresh air; obtain medical attention if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Spill/Disposal (general):

  • Absorb small spills with inert material; collect for disposal. Dispose in accordance with local regulations; avoid drain release.

Always consult the product-specific SDS before use.

Solvent Selection

This compound is an organosulfur reagent of moderate polarity with limited water solubility and broad solubility in organic media.

• General polarity/miscibility (literature-based):

  • Prefers aprotic organic solvents: dichloromethane (DCM), chloroform, toluene, ethyl acetate, THF, acetonitrile.
  • Water: expected low solubility; emulsions possible due to surface activity of the dithiocarbamate motif.

• Choosing a solvent by task (practical guidance):

  • Nucleophilic substitutions or Pd-allylation studies: THF, MeCN, or DCM under anhydrous conditions.
  • Radical or RAFT-type transformations: toluene, dioxane, or bulk monomer media; ensure oxygen exclusion.
  • Metal complexation or extraction: DCM/CHCl3 or toluene for phase-transfer capture of soft metals (Cu, Ni, Pd) followed by back-extraction.
  • Chromatography: silica can interact via soft acid–base contacts; start with hexanes/EtOAc or toluene/EtOAc gradients; add 0.1–1% Et3N if tailing is observed (general tip for thiocarbonyl compounds).

• Small comparison (literature-informed):

  • vs. Alcohols (MeOH/EtOH): better stability in aprotic media; avoid protic solvents during storage to minimize hydrolysis.
  • vs. Polar amide solvents (DMF/DMAc): dissolve well but may complicate workup and promote side reactions at elevated temperature.

Note: Exact solubility and UV-cutoff for this item are not specified; verify with your lot’s CoA or a quick solubility/UV scan.

Storage and Reconstitution

• Item-specific storage/shipping (from Product Data):

  • Storage Conditions: Room temperature, Cool. Store in a cool, dry place.
  • Shipped In: Normal.

• General storage guidance for dithiocarbamates:

  • Keep container tightly closed, under inert gas (nitrogen/argon) if possible, to limit oxidation.
  • Protect from light and moisture; use amber glass and desiccant.
  • Avoid contact with acids, strong oxidizers, and reactive metals.
  • Minimize headspace and repeated opening; consider aliquoting for long-term projects.

• Stability monitoring:

  • Check periodically by 1H NMR/IR for new signals or loss of C=S intensity; inspect for color changes or precipitates.

• Reconstitution/handling:

  • If solidified or viscous, warm gently to ambient temperature and vortex/sonicate.
  • Prepare solutions in dry, oxygen-free organic solvents (e.g., DCM, toluene, MeCN, THF). Use freshly prepared solutions for sensitive transformations.

For exact shelf-life and any stabilizers present, consult the lot-specific CoA and SDS. Product is for research use only.

Structure and Identity

Allyl Dimethyldithiocarbamate is an S-allyl ester of a dimethyl dithiocarbamic acid, featuring a thiocarbonyl (C=S) flanked by a dimethylamino group and a thioether-bound allyl substituent.

• Item-specific identifiers (from Product Data):

  • CAS: 20821-66-3
  • SKU: A151292
  • InChIKey: 455576 (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/computed identifiers and descriptors (general reference; not item specifications):

  • Common structural depiction: S-allyl N,N-dimethyldithiocarbamate with connectivity N(CH3)2–C(=S)–S–CH2–CH=CH2.
  • Typical SMILES (literature): CN(C)C(=S)SCC=C or C=CCSC(=S)N(C)C (synonymous representations).
  • Typical molecular formula (literature): C6H11NS2; formula mass ~161.29 g/mol (literature).

• Structural features (general):

  • Functional groups: dithiocarbamate (thiocarbonyl C=S adjacent to a dialkylamino), thioether linkage to an allyl group (terminal alkene).
  • Hybridization and conjugation: The C=S is polarized and conjugated with the nitrogen lone pair (thiourea-like resonance), imparting soft nucleophilicity at sulfur and ligand character toward soft metals.
  • 2D description: Dimethylamino carbonyl-thio center with a second sulfur bearing an allyl chain (–CH2–CH=CH2); no stereocenters; one terminal C=C.

Synthetic Utility

Allyl Dimethyldithiocarbamate is a compact platform combining an allylic sulfide with a dithiocarbamate, offering multiple orthogonal reaction handles.

• Functional group leverage (literature/general):

  • Thiocarbonyl (C=S): Enables radical chemistry, serves as a soft Lewis base for metal coordination, and provides a UV-visible chromophore for monitoring.
  • Dithiocarbamate moiety: Acts as a leaving group or transferable fragment in substitutions and rearrangements; amenable to conversion into isothiocyanate/thiourea derivatives under appropriate conditions.
  • Allylic C=C: Participates in thiol–ene additions, allylic substitutions (Pd-catalyzed), epoxidation/hydroxylation (if desired downstream), or radical additions.

• Named/related transformations (contextual):

  • Tsuji–Trost allylation (using suitable electrophiles; the allyl thioether fragment may be utilized or transformed under Pd catalysis).
  • Barton–McCombie-type strategies by analogy with xanthates for deoxygenation when interconverted to the appropriate thiocarbonyl derivative.
  • [2,3]-Sigmatropic rearrangements of allyl sulfur systems (substrate/condition-dependent), enabling C–C bond formation from C–S precursors.

• Retrosynthetic value:

  • Serves as a masked allyl thiolate or dithiocarbamate synthon. Cleavage of the S–allyl bond (e.g., nucleophilic or radical) can reveal different sulfur oxidation states or exchange partners.

Practical considerations:

• Maintain anhydrous, oxygen-limited conditions.
• If silica gel chromatography causes tailing, use basic modifiers (0.2–1% Et3N) or alumina as stationary phase.

Target Specificity

This product is a small-molecule reagent, not a biological targeting agent or antibody.

• Item-specific targeting data (antigen/epitope/clone/isotype/species): Not applicable.

For target-selective applications, consider pairing this reagent with appropriate catalysts, ligands, or derivatization strategies tailored to your system.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store in a cool place.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

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

The CAS Number is 20821-66-3, the molecular formula is C6H11NS2, and the molecular weight is 161.28 g/mol. InChIKey ZFMLVJCASVPGIT-UHFFFAOYSA-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.