This compound belongs to the class of organic compounds known as sulfuric acid diesters. These are organic compounds containing the sulfuric acid diester functional group with the generic structure ROS(OR')(=O)=O, (R,R'=organyl group).
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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.
1.Lei Chen, Wei Yin, Qifan Yu, Menghua Qi, Man Wang, Bingjie Wang. (2025) Efficient and selective mercaptans removal from aviation kerosene by porous alkaline alumina adsorbents: Synthesis, characteristics and application. SEPARATION AND PURIFICATION TECHNOLOGY, [PMID:][10.1016/j.seppur.2025.134342]
2.Jie Zhong, Xin Yi Bai, Zhuo Zhang, Xiao Gang Li, Jun Zi Zhu. (2025) Biocontrol potential of Streptomyces lactacystinicus producing volatile organic compounds against postharvest anthracnose of chili pepper. POSTHARVEST BIOLOGY AND TECHNOLOGY, [PMID:][10.1016/j.postharvbio.2025.113758]
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Application Protocols
No standardized biological assay protocols are specified for this item. As a chemical reagent, usage depends on the synthetic transformation being targeted.
General synthetic protocol sketch (literature/general):
Dry glassware and solvent; charge nucleophile and base under inert atmosphere.
Cool if necessary; add dibutyl sulfate slowly with stirring.
Heat to target temperature (as needed) and monitor by TLC/GC/HPLC.
Quench into aqueous base; extract, wash, dry, concentrate, and purify by chromatography or crystallization.
For any application-specific methods, consult your lab SOPs and adapt conditions to your substrate. Always refer to the product’s SDS for safe handling steps.
Biological Roles
This product is intended strictly for research use; no biological role is claimed for the catalog item.
General context (literature/biochemistry):
Endogenous occurrence: Dialkyl sulfates like dibutyl sulfate are not known endogenous metabolites; they are synthetic sulfate diesters.
Reactivity with biomolecules: As alkylating agents, dialkyl sulfates can react with nucleophilic residues in biomolecules (e.g., thiols, amines), which underlies their general cytotoxic/irritant properties in biological systems.
Metabolic fate (general): In aqueous/physiological environments, slow hydrolysis to butanol/butyl hydrogen sulfate or sulfate species can occur; rates depend on pH and temperature.
Practical implication for researchers:
Avoid contact with biological materials unless the experimental design specifically tests chemical reactivity. Use appropriate containment when handling around cell cultures, proteins, or nucleic acids.
No clinical, therapeutic, or diagnostic use is implied or permitted.
Buffer Applications
Dibutyl sulfate is not a buffering agent and is not typically used to prepare biological or analytical buffers. Its hydrolysis and strong electrophilicity are incompatible with maintaining stable pH systems.
If your workflow involves buffers, select a dedicated buffer system (e.g., phosphate, HEPES, acetate) and conduct any alkylation steps in a separate, aprotic organic phase or biphasic system where the buffer provides base only via phase-transfer catalysis.
For buffer recipes and pH control, consult reagents specifically designed for buffering; this product is unsuitable for that role.
Green Alternatives
While dibutyl sulfate is effective for n‑butyl transfer, dialkyl sulfates are potent alkylating agents with notable hazard profiles. Consider greener or safer electrophiles and solvents where feasible.
1-Butyl acetate or butyl carbonate derivatives activated under catalytic conditions (e.g., carbonate-based alkylations) – reduced acute toxicity; may require catalysts (e.g., TBD, alkali bases) and higher temperatures.
1-Bromobutane/1-chlorobutane or butyl tosylate/mesylate – operationally simpler; halides are less inherently reactive than sulfates but can present lower chronic toxicity concerns. Tradeoff: halides generate halide waste and may require stronger bases/longer times.
Enzymatic or biocatalytic butylations (for esters) using lipases with n‑butanol – excellent EHS profile but scope limited to acyl transfer rather than C–O/C–N/C–S butylation.
Greener solvent swaps (for the reaction medium):
Polar aprotic greener choices: Acetonitrile (with recovery), propylene carbonate (high bp, minimal VOC), or 2‑MeTHF/EtOAc vs DMF/DMSO.
Comparison (high level):
Dibutyl sulfate: high reactivity; significant alkylation hazard; hydrolysis waste is sulfate.
Butyl tosylate: moderate reactivity; p‑TsO− waste; often safer handling vs sulfate esters.
2‑MeTHF medium: renewable, good workup; may need higher temperature.
Selecting a greener route requires balancing EHS, process mass intensity, waste profile, and selectivity for the specific substrate.
Pharmaceutical Uses
No excipient or clinical use is claimed. For research use only.
Alkylating reagent in API/intermediate synthesis: Dibutyl sulfate can serve as an n‑butyl donor for O‑, N‑, or S‑alkylation when synthesizing hydrophobic protecting groups, pro-moieties, or tailoring side chains during medicinal chemistry campaigns.
Quaternization steps: Though less common than methyl/ethyl sulfates, it may be used to quaternize tertiary amines to produce butylammonium salts in process development.
Considerations for process chemists:
Evaluate impurity profiles (over-alkylation, transesterification, hydrolysis) and define purge strategies.
Implement robust containment due to alkylation hazard; closed charge, in-line quench, and validated cleaning procedures.
Prefer greener media (e.g., 2‑MeTHF, EtOAc, MeCN with recovery) and consider alternative electrophiles if EHS or impurity control is challenging.
Regulatory note: This reagent is not an approved pharmaceutical ingredient or excipient; any use in GMP settings requires full risk assessment, specification setting, and vendor qualification.
Physical Properties
Item-specific specifications (grade-specific cutoffs, stabilizers, and numeric assays) are not provided in the Product Data.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet. (Literature: ~210.29 g/mol for C8H18O4S.)
Molecular Formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet. (Literature: C8H18O4S.)
Boiling behavior (literature): Dialkyl sulfates typically have high boiling points and may undergo decomposition on prolonged heating; di-n-butyl sulfate is reported to have a high bp with potential thermal decomposition rather than clean distillation at ambient pressure.
Melting point (literature): Often liquid at room temperature; specific mp not widely reported for the n-butyl diester.
Density (literature): Expected near or slightly above 1 g/mL at 20–25 °C; consult specific supplier data for exact value.
Solubility (literature/general):
Low solubility in water; slow hydrolysis in aqueous media can occur, especially under acidic or basic conditions.
Miscible with many organic solvents (e.g., ethers, chlorinated solvents, aprotics such as DMF/DMSO, and esters). Polar aprotic media often used for reactions.
LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet (literature values vary and are method-dependent).
Always verify exact physical constants on the item’s CoA for method-specific numbers used in process design.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting potential grades (general):
Analytical/AR grade: Tight controls on purity and common inorganic/organic residues; appropriate when the reagent serves as a titrant or for analytical derivatization where background must be minimized.
Reagent grade: Suitable for most synthetic applications; trace metals/UV-absorbing impurities are not necessarily limited to chromatographic specifications.
HPLC grade (if applicable): Emphasis on low UV background and low nonvolatile residue; relevant only if the reagent is being used as a mobile-phase component or needs optical clarity.
Stabilizers and additives:
Dialkyl sulfates are typically shipped neat without stabilizers; any presence/absence of inhibitors should be taken from the item CoA. Additives, if used, can influence reactivity in SN2 processes.
What to check on receipt:
Water content (Karl Fischer), acidity (acid number), color (APHA), and assay by qNMR/GC are common QC parameters for this class. For this specific item, only the supplier CoA defines acceptance criteria.
Note: No medical or clinical use is intended; this material is offered strictly for research and laboratory applications.
Reaction and Applications
Dibutyl sulfate functions as an electrophilic n-butylating agent via SN2 displacement on one of its primary alkyl groups.
Key transformations (literature/general):
O-Butylation of alcohols/phenols: Formation of n-butyl ethers using alkoxides/phenoxides. Base choices include NaH, K2CO3, Cs2CO3, or t-BuOK depending on substrate. Typical solvents: acetonitrile, DMF, DMSO, 2-MeTHF. Reaction temperatures 25–80 °C; elevated temperatures accelerate sluggish substrates.
S-Butylation of thiols: Rapid generation of thioethers with thiolates; often proceeds at lower temperatures than O-alkylation.
N-Butylation of amines: Primary/secondary amines can be N-alkylated; tertiary amines can undergo quaternization to form butylammonium salts (pace slower than methyl/ethyl analogs). Control over mono‑ vs di‑alkylation requires base and stoichiometry optimization.
C-Butylation (activated carbon): In special cases (e.g., enolates, malonates), C-alkylation can be achieved; however, n-butyl halides/tosylates are more common for such steps.
Mechanistic/practical notes:
Reaction proceeds by SN2 attack on a primary n‑butyl chain, releasing a sulfate monoester as the leaving group.
Water exclusion is important to avoid hydrolysis. Dry glassware, molecular sieves, or azeotropic drying recommended.
Order of addition: Slow addition of dibutyl sulfate to a pre-formed nucleophile/based solution mitigates exotherm and minimizes side hydrolysis.
Workup: Quench with dilute base; extract into organic; sulfate byproducts partition into aqueous as sulfate/sulfonate species upon hydrolysis.
Applications include protecting group strategies (tBu-n-butyl ethers are less common than benzyl), solubility modulation via butylation, and synthesis of hydrophobic analogs for SAR studies.
Reaction Conditions
General, literature-derived guidance for using dibutyl sulfate as an n‑butylating agent. Optimize for your substrate; these are starting points only.
O‑Butylation (phenols/alcohols):
Base: K2CO3 or Cs2CO3 (1.5–2.0 equiv) for phenols; NaH or t‑BuOK (1.1–1.5 equiv) for alcohols.
Solvent: MeCN, DMF, DMSO, or 2‑MeTHF.
Temperature: 25–80 °C; 50–70 °C often sufficient for phenols.
Time: 2–16 h depending on nucleophile and temperature.
Notes: Add dibutyl sulfate slowly to pre-formed alkoxide/phenoxide; maintain anhydrous conditions. Monitor by GC/HPLC.
S‑Butylation (thiols):
Base: Na2CO3/K2CO3 or NaH for sluggish cases.
Solvent: MeCN, DMF, or EtOAc (where soluble).
Temperature: 0–40 °C typically adequate; reactions often rapid.
N‑Butylation (amines):
Base: Triethylamine or Na2CO3; for tertiary amine quats, use neat or MeCN and mild base.
Temperature: 25–60 °C.
Considerations: Control equivalents to limit over-alkylation; quench and basify to decompose residual sulfate esters.
Workup: Quench into aqueous bicarbonate or dilute base; extract organic product with EtOAc or toluene; wash to remove sulfate species; dry and concentrate. Residual sulfate byproducts can be purged via aqueous washes.
Typical yields: Strongly substrate-dependent; many O/S-alkylations report good to excellent conversions under optimized conditions (literature). Always validate on small scale.
Safety: Use a fume hood; control exotherms; avoid contact with protic media that may release heat and acidic species.
Safety and Handling
Hazard classifications are not provided in the Product Data. Dialkyl sulfates are generally potent alkylating agents and should be handled with heightened caution.
GHS (item-specific): Not specified for this item; refer to SDS for authoritative classification, pictograms, and H/P statements.
Primary hazards (general for dialkyl sulfates):
Strong irritants/corrosives to skin, eyes, and respiratory tract; risk of sensitization is possible.
Alkylating activity can lead to severe eye damage and chemical burns on contact; inhalation of vapors/aerosols should be strictly avoided.
Hydrolysis can generate acidic species; thermal decomposition may release sulfur oxides.
PPE: Chemical-resistant gloves (e.g., butyl rubber, Viton; verify compatibility), lab coat, splash goggles/face shield. Use in a certified chemical fume hood.
Incompatibilities: Strong bases (rapid decomposition/alkylation), strong acids (accelerated hydrolysis), strong nucleophiles, moisture (slow hydrolysis), and oxidizable organics under strongly acidic conditions. Avoid contact with amines, azides, thiols without appropriate controls.
First aid (overview; consult SDS):
Skin/eye contact: Immediate decontamination with copious water for ≥15 min; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air; support breathing; medical evaluation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical care.
Ethers/esters: THF, 2-MeTHF, MTBE, EtOAc – useful when solubility permits; often require phase-transfer or base selection to maintain reactivity.
Biphasic systems: Toluene/CH2Cl2 with aqueous base and a PTC (e.g., quats) for phenolates or carboxylates.
When to choose which:
Use acetonitrile/DMF for difficult nucleophiles or lower temperatures.
Choose 2-MeTHF/EtOAc when greener solvent profile is desired and nucleophile is sufficiently reactive.
Employ biphasic + PTC for heterogeneous bases or scale-up robustness.
Avoid/Use caution: Protic solvents (MeOH, H2O) can compete via hydrolysis or transesterification; strong basic aqueous media accelerates decomposition.
Small comparison (general):
Acetonitrile: fast SN2, easy workup, good volatility.
DMF/DMSO: strong rate enhancement but challenging removal; watch for thermal stability.
2-MeTHF/EtOAc: greener, easier removal; may require higher temp or stronger base.
Storage and Reconstitution
Storage Conditions (item-specific from Product Data): Protected from light; Room temperature; Argon charged.
Shipped In: Normal.
Container recommendations (general): Store in a tightly sealed, moisture-free, amber glass bottle with inert headspace (argon or nitrogen) to minimize hydrolysis and oxidation. Avoid contact with reactive metals.
Handling: Minimize air/moisture exposure; use dry syringes or positive-displacement pipettes. Wipe spills promptly; prevent residue accumulation on caps/septa.
Stability considerations: Dialkyl sulfates can hydrolyze slowly in the presence of moisture and may decompose upon prolonged heating. Maintain in the dark at ambient temperature as specified; refrigeration is typically unnecessary unless otherwise noted on CoA.
Reconstitution: Supplied neat (no reconstitution required). If dilution is required for dosing or stock solutions, prepare in anhydrous aprotic solvent (e.g., MeCN, 2‑MeTHF, DMF) immediately before use and store only short-term in sealed vials under inert gas.
Freeze–thaw: Not applicable to neat liquids; if solutions are prepared, avoid repeated freeze–thaw cycles which can introduce moisture upon warming.
Always consult the batch-specific CoA and SDS for definitive storage and stability information.
Structure and Identity
Dibutyl sulfate is the di-n-butyl ester of sulfuric acid — a dialkyl sulfate alkylating reagent.
SKU: D154808
Product Name: Dibutyl Sulfate
CAS: 625-22-9
PubChem CID: 12239
InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet. (A literature InChIKey exists for di-n-butyl sulfate.)
SMILES (literature): CCCCOS(=O)(=O)OCCCC
Molecular Formula (literature): C8H18O4S
Molecular Weight (literature): ~210.29 g/mol
Structural features (general description):
Functional groups: Sulfate diester (–OSO2O–) linking two n-butyl chains.
Backbone: Tetrahedral sulfur(VI) center doubly bonded to two oxygens and single-bonded to two bridging oxygens that each connect to a primary n-butyl group (–CH3–CH2–CH2–CH2–O–SO2–O–(CH2)3–CH3).
Stereochemistry: None (achiral, no stereocenters).
2D description in words: A central sulfate group [S(=O)2] connected via –O– linkages to two straight-chain butyl residues; overall neutral diester.
Notes:
Identifiers and composition above (other than CAS/CID) are provided as literature identity for the named substance. For exact item identifiers (e.g., supplier-confirmed InChIKey), consult the product CoA/Spec Sheet.
Synthetic Utility
Functional handle: a symmetric sulfate diester bearing two primary n‑butyl groups. Reacts as a bifunctional electrophile capable of transferring a single n‑butyl group in SN2 processes.
Electrophile profile: Primary-alkyl SN2 donor; the departing fragment is a sulfate monoester (good leaving group). Favorable for nucleophiles that struggle with poorer electrophiles (e.g., chloride).
O‑Alkylation: Generation of n‑butyl ethers from alcoholates/phenolates; useful when increased lipophilicity or blocking of hydrogen-bond donors is desired.
S‑Alkylation: Efficient formation of thioethers (n‑butyl sulfides) from thiolates.
N‑Alkylation: Butylation of amines; control over selectivity (mono- vs di- vs quaternization) is substrate- and condition-dependent.
Complementarity: Compared to 1‑bromobutane or butyl tosylate, dibutyl sulfate can be more reactive under milder conditions but demands stricter safety and moisture control.
Protecting-group chemistry: While n‑butyl ethers are not classical protecting groups, they can serve as durable blocking groups for harsh conditions where deprotection is not required until late-stage hydrogenolysis/cleavage strategies (often requiring more forcing conditions or alternative routes).
Retrosynthesis tips:
When a target demands selective n‑butylation on a weakly nucleophilic oxygen or sulfur, consider dibutyl sulfate in a polar aprotic solvent with non-nucleophilic base and controlled addition to suppress competing hydrolysis.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent (not an antibody, enzyme, or biological probe). No antigen/epitope or species reactivity applies.
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