This compound belongs to the class of organic compounds known as pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.
External Descriptors
Not available
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.
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Application Protocols
No item‑specific, tested bioassay protocols are provided for this product. It is a small‑molecule reagent rather than an antibody/enzyme.
General laboratory usage examples (informational; adjust to your method)
GC/GC‑MS reference solution: Prepare 1.0 mg/mL in iso‑octane (or methanol for LC). Filter through 0.2 µm PTFE if particulate is present. Store in crimp‑sealed vials at 4–8 °C for short‑term stability; equilibrate to room temp before use.
HS‑SPME spike: Add known µg/L quantities into matrix, equilibrate at 40–60 °C, extract with PDMS/DVB fiber, desorb in injector; validate recovery and linearity.
Benzylic bromination screen: Dissolve substrate (0.2 M) in EtOAc, add NBS (1.1 eq), AIBN (5 mol%), irradiate 365–405 nm, monitor by GC every 30 min; quench, wash, and analyze.
Note
These are generalized research examples. Optimize for your instrumentation and safety standards. Always consult the SDS and your institutional SOPs before use.
Biological Roles
This section provides general biochemical context for pyrazine derivatives; it does not imply biological activity or suitability for clinical/food use for this specific catalog item.
Pyrazine core in biology: The pyrazine ring appears in natural products and cofactors (e.g., the pyrazine substructure is part of some pteridines and biopterins). The heteroaromatic diazine motif can engage in π–π stacking and hydrogen‑bond acceptance with biomacromolecules.
Alkylpyrazines in nature (literature): Various alkylpyrazines have been reported as volatile metabolites from microorganisms and plants and are used in analytical studies as reference standards for metabolomics and volatilome profiling.
Physicochemical determinants: The dual ring nitrogens reduce basicity compared to pyridine, influencing protonation states under physiological pH. The isobutyl substituent increases hydrophobicity, potentially enhancing partitioning into lipid phases or headspace in volatilomics experiments.
Research relevance: In vitro studies may use alkylpyrazines to probe heteroaromatic recognition, to calibrate HS‑SPME/GC‑MS methods, or to study structure–volatility relationships.
Important note
No medical, nutritional, or therapeutic claims are made. This product is for research use only, as stated in the Product Data. Any biological experimentation should follow institutional biosafety and chemical hygiene protocols.
Buffer Applications
Not typically applicable. (2‑Methylpropyl)pyrazine is a neutral organic heteroaromatic, not a classical buffering agent. It does not provide a well‑defined conjugate acid/base pair in the physiological pH range with suitable capacity.
Practical note
If included in aqueous systems (e.g., analytical spikes), use an appropriate external buffer such as phosphate (pH 6–8), acetate (pH 4–5.5), or citrate (pH 3–6). Ensure the compound’s solubility in the chosen aqueous/organic mixture (co‑solvents like MeOH, ACN, or DMSO may be required at low percentages).
Green Alternatives
Sustainability considerations (general for alkylpyrazines)
Hazard profile: Alkylpyrazines are organic liquids with combustible and irritant properties. While not among the most hazardous aromatics, minimizing VOC emissions and solvent use is desirable.
Solvent footprint: When using this compound as an analytical standard or reagent, prefer greener diluents (EtOH, i‑PrOH, MeCN with proper recovery) over chlorinated solvents where feasible.
Potential greener substitutes by function
Analytical aroma markers: Consider shorter‑chain alkylpyrazines (e.g., ethyl‑/isopropylpyrazine) if adequate for separations, as they often require less heating in GC and may lower energy use.
Heteroaromatic donors in coordination studies: Pyrazine itself or 2,6‑dimethylpyrazine may provide similar binding motifs with differing volatility; selection depends on safety and waste considerations.
Use micro‑scale standards and sealed autosampler vials to reduce evaporative losses.
Implement solvent recycling (fractional distillation for alcohols/esters) and closed‑loop ventilation.
Opt for catalytic over stoichiometric oxidants/reductants in transformations (e.g., H2 with reusable Pd/C, electrochemical routes) and aqueous or bio‑derived solvents where compatible.
Pharmaceutical Uses
Formulation/excipient context (general)
This compound is not a standard pharmaceutical excipient. Alkylpyrazines are more commonly encountered as analytical reference materials or synthetic intermediates in medicinal chemistry programs.
Analytical roles in pharma R&D
Can serve as a GC/LC reference standard or system‑suitability marker in method development involving heteroaromatic volatiles.
Potential internal or external standard in headspace GC studies due to moderate volatility and distinctive mass spectrum (literature practice), contingent on validation.
Regulatory status
No pharmacopeial monograph is known for (2‑methylpropyl)pyrazine. For GMP contexts, suitability must be justified via compendial‑neutral qualification: identity, purity, residual solvents, and elemental impurities per ICH Q3A/Q3C/Q3D as applicable.
Important
No therapeutic or clinical use is claimed or implied. This product is offered strictly for research and laboratory use, consistent with the Product Data note: For research use only.
Physical Properties
Item-specific properties (specifications)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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.
General/literature physicochemical profile for alkylpyrazines (for context; not product specifications)
State: Typically colorless to pale yellow liquid with characteristic pyrazine/aromatic odor.
Boiling point: Commonly in the ~180–210 °C range for C4‑alkylpyrazines (literature). Exact value depends on isomer and purity.
Melting point: Generally below room temperature (liquid at ambient; literature).
Density (20–25 °C): Around 0.93–1.00 g/mL for related alkylpyrazines (literature).
Refractive index (nD20): Often ~1.49–1.52 for comparable heteroaromatics (literature).
LogP: Moderately hydrophobic; cLogP typically ~1.0–1.6 for C4‑alkylpyrazines (computed/literature).
pKa: Ring nitrogens are weak bases; conjugate acid pKa typically ~0.6–1.0 (literature), reflecting low basicity of pyrazine.
Solubility: Moderately soluble in water (via heteroatoms) but more soluble in organic solvents (alcohols, ethers, esters, chlorinated, aromatics) — literature trend for alkylpyrazines.
Notes
The above values are provided for planning and comparative purposes only. For this specific catalog item, consult the CoA/Spec Sheet for definitive specifications.
Quality and Grades
Item-specific grade and stabilizers
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
Research grade: Suitable for synthetic, analytical, and discovery work. Typical focus is on identity and purity by GC/HPLC/GC‑MS and water/volatile content as applicable.
High‑purity or GC grade (if specified on CoA): Indicates tighter control of trace impurities and often lower background for chromatographic detection (low UV absorbance/bleed).
Aroma reference standard grade (when offered by some vendors): Emphasizes identity and purity for sensory/analytical calibration; not for food use unless explicitly certified.
What to check on the CoA/Spec Sheet for this material
Identity confirmation: GC‑MS/NMR consistent with an isobutyl‑substituted pyrazine isomer; single major chromatographic peak.
Purity method: GC area percent or quantitative NMR; note any residual solvents.
Volatile impurities: Water content (Karl Fischer) and residual low boilers if relevant — Not specified for this item; refer to CoA/Spec Sheet.
UV/trace metals: Typically not critical for this class; if your application is photochemical or catalytic, verify limits — Not specified for this item; refer to CoA/Spec Sheet.
Fit‑for‑purpose advice
For trace‑analysis or olfactometry method development, prioritize lots with tight GC purity and low baseline noise.
For synthesis, evaluate inhibitor/stabilizer status (if any) to understand downstream compatibility (none specified here).
Reaction and Applications
Research applications (general; expandability from a pyrazine building block)
Analytical chemistry: Frequently used as an alkylpyrazine reference/standard in GC/GC‑MS method development, aroma/volatilome profiling, and pattern recognition studies (literature). Its moderate volatility and single heteroaromatic chromophore aid detection.
Heteroaromatic chemistry: Serves as a substrate or benchmark for studying pyrazine ring electronics (two diazine nitrogens render the ring electron‑deficient), affecting reactivity in electrophilic vs. nucleophilic substitution and in hydrogenation.
Coordination chemistry: The ring nitrogens can serve as weak donors to Lewis acids/transition metals; alkyl substitution modulates binding affinity and sterics.
Transformations (literature examples)
N‑oxidation: Formation of pyrazine N‑oxides with peracids or H2O2/UHP systems, useful for further functionalization via Polonovski‑type chemistry.
Benzylic functionalization: Radical or bromination pathways at the benzylic CH2 (–CH2–) under NBS/AIBN or photochemical conditions, enabling subsequent substitution (e.g., to alcohols, amines, nitriles).
Hydrogenation: Catalytic hydrogenation can reduce the pyrazine to piperazine derivatives or partially hydrogenate the ring; conditions tuned to avoid over‑reduction.
Lithiation/Metalation (directed): Though pyrazines are deactivated to EAS, strong bases (e.g., s‑BuLi/TMEDA, low temperature) can effect metalation at appropriate positions for subsequent electrophile trapping (literature).
Practical tips
Drying: If required water‑sensitive steps are planned, dry over molecular sieves (3Å/4Å) or by brief distillation under inert gas.
Degassing: For air‑sensitive catalysis, sparge solutions with N2/Ar and use Schlenk techniques.
Monitoring: GC‑FID/GC‑MS is highly effective due to volatility and distinct mass spectral fingerprints of alkylpyrazines.
Reaction Conditions
General literature guidance for transformations involving alkylpyrazines (non‑specific; adjust to substrate and scale):
Benzylic bromination (radical)
Typical: NBS (1.1–1.2 eq), AIBN or benzoyl peroxide (cat.), refluxing CCl4, CCl2F2, or greener alternatives like EtOAc or MeCN under photochemical initiation (hv, 365–405 nm). 1–6 h. Monitor by GC.
Workup: Quench, wash with bicarbonate, and purify by column or distillation.
N‑Oxidation
Reagents: mCPBA (1.1–1.5 eq) in DCM at 0–25 °C, or H2O2/UHP with acetic acid or MeOH as solvent. 1–12 h.
Notes: Control exotherm; avoid over‑oxidation. N‑oxide increases polarity and alters basicity.
Hydrogenation
Conditions: H2 (1–10 bar) with Pd/C (5–10 wt%) or Raney Ni in EtOH/EtOAc/AcOH at 20–60 °C, 2–16 h. Partial vs. full ring saturation depends on catalyst/load/pressure.
Caution: Over‑reduction to piperazine derivatives possible; verify by NMR/GC‑MS.
Base: s‑BuLi or t‑BuLi with TMEDA at −78 to −40 °C in THF. Quench with electrophiles (CO2, aldehydes, trialkyl chlorosilanes). Low temperature critical to control regioselectivity.
Benzylic oxidation (milder)
Conditions: Oxidants like TEMPO/NaOCl (aqueous biphasic), or MnO2 to form the corresponding aldehyde/ketone from the benzylic bromide/alcohol intermediates.
Yield expectations
Literature yields for these classes span 50–90% depending on substrate/catalyst and control of side reactions. Always perform small‑scale scouting.
Safety and Handling
Item-specific hazard information
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety profile for alkylpyrazines (informational; consult SDS for this product)
Likely hazards: May cause skin/eye irritation and respiratory tract irritation. Many low‑volatility heteroaromatics can be combustible; treat as flammable combustible liquid, especially as a heated vapor.
Precautions: Use in a chemical fume hood. Avoid breathing vapors/mists. Prevent release to the environment.
Recommended PPE and controls
PPE: Lab coat, safety glasses or splash goggles, and appropriate chemical‑resistant gloves (e.g., nitrile). Consider double‑gloving for extended contact.
Engineering controls: Local exhaust/fume hood. Closed‑transfer where feasible.
Incompatibilities and reactivity (general)
Strong oxidizers (risk of exothermic reactions/oxidation).
Strong acids can form pyrazinium salts; strong bases may promote side reactions (e.g., deprotonation at benzylic CH2 under forcing conditions).
Elevated temperatures can increase vapor concentration; adopt heat‑source controls.
First‑aid (overview; defer to SDS)
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical advice for persistent irritation.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical attention.
Spill/Fire response (general)
Spills: Absorb with inert material (vermiculite), ventilate area, dispose per regulations.
Fire: Use CO2, dry chemical, or foam; cool containers with water spray.
Solvent Selection
Compound solvent behavior (general)
Polarity: Moderately polar heteroaromatic (two ring nitrogens) bearing a hydrophobic isobutyl side chain; overall amphiphilic.
Dielectric/miscibility: Expected miscible with most organic solvents (alcohols, ethers, esters, ketones, aromatics, halogenated). Limited to moderate water miscibility (literature trend for C4‑alkylpyrazines).
Choosing media for handling/analysis
Neat handling: Often a liquid at room temperature; can be dosed neat by microsyringe for GC/GC‑MS work.
Dilution solvents for analytics: Ethanol, methanol, acetonitrile, isopropanol, dichloromethane, or hexanes/toluene depending on detector and column phase. For GC‑FID, nonpolar diluents (hexane, iso‑octane) minimize early solvent interference; for LC‑MS, MeOH/ACN with 0.1% FA (if ionization as [M+H]+ is desired).
Compatibility considerations
Avoid strongly acidic aqueous media if free‑base form must be maintained (protonation to pyrazinium salts reduces volatility and GC amenability).
In basic media, benzylic CH2 next to the ring can be activated under strong base; preserve integrity by avoiding prolonged exposure to strong bases at elevated temperature.
Comparison with alternatives (general)
Versus smaller alkylpyrazines: Lower volatility and higher hydrophobicity can aid late‑eluting GC separation and reduce evaporative losses.
Versus higher alkylpyrazines: Better solubility in polar organics and typically cleaner LC‑MS ionization due to balanced polarity.
Storage and Reconstitution
Storage conditions (from Product Data)
Storage temperature: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling and stability guidance
Container: Store in a tightly sealed amber glass bottle to minimize volatilization and light exposure. Use PTFE‑lined caps to reduce permeation.
Atmosphere: For long‑term storage, blanket headspace with inert gas (N2/Ar) after opening to limit oxidative changes, especially if frequent sampling occurs.
Segregation: Keep away from strong oxidizers and strong acids/bases. Secondary containment advised.
Reconstitution/Preparation
This product is typically supplied neat. If a stock solution is required, prepare in a compatible solvent (e.g., methanol, ethanol, acetonitrile, hexanes, toluene, DCM) at a convenient concentration (e.g., 1–100 mg/mL), filter if necessary through PTFE (0.2 µm), and label with solvent, concentration, date, and preparer.
Stability of solutions: At ambient conditions, alcoholic or hydrocarbon solutions are generally stable for days to weeks in sealed vials; for LC‑MS work, prepare fresh weekly. Refrigeration (2–8 °C) of sealed standards can extend shelf life; allow to warm to room temperature before opening to avoid moisture condensation.
Research use note
For research use only, as stated in the Product Data.
Structure and Identity
Brief description: (2‑methylpropyl)pyrazine is an alkyl‑substituted pyrazine, i.e., a six‑membered, planar, aromatic diazine ring (N atoms at positions 1 and 4) bearing a branched C4 alkyl (isobutyl) side chain.
Item-specific identifiers (from Product Data)
SKU: P1068524
Product Name: Pyrazine, (2-methylpropyl)-
CAS: 29460-92-2
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data shows: 432100, which is incomplete/non-standard.)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structure features (general/literature description)
Core ring: Pyrazine (1,4-diazine) — aromatic, two ring nitrogens opposite each other; electron deficient relative to benzene.
Substituent: (2‑methylpropyl) = isobutyl group (–CH2–CH(CH3)2), typically attached to a ring carbon (positional isomers are known in the literature).
Functional groups: aromatic heterocycle (Lewis basic N sites), hydrophobic branched alkyl side chain.
Stereochemistry: None (no stereogenic centers in the parent isobutyl substituent when attached via the CH2).
Molecular formula and mass
Item-specific formula: Not specified for this item; refer to CoA/Spec Sheet.
Item-specific molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature (typical for C4-alkylpyrazines, mono-substituted): C8H12N2; calculated M r ≈ 136.20 g/mol (literature/computed).
Synthetic Utility
Functional group landscape
Aromatic diazine (pyrazine) ring: Electron‑deficient vs. benzene/pyridine; two ring nitrogens serve as weak Lewis bases and hydrogen‑bond acceptors.
Benzylic CH2 in the isobutyl substituent: Amenable to selective activation (radical, ionic) enabling further elaboration without pre‑functionalizing the ring.
Strategic uses (literature/general)
Benzylic derivatization platform: Convert –CH2– into bromide (NBS/AIBN), alcohol (via radical bromination then hydrolysis), amine (via azide displacement → Staudinger/reduction), or nitrile (cyanation), enabling parallel SAR generation around a constant heteroaromatic core.
Ring‑centric diversification: Though direct EAS is disfavored, directed metalation (e.g., s‑BuLi/TMEDA at low T) or Minisci‑type radical acylation/alkylation under protonated/N‑oxide conditions can introduce additional substituents.
Oxidation/reduction toggles: N‑oxidation (mCPBA, H2O2/UHP) allows subsequent rearrangements or serves as a handle for differential coordination; catalytic hydrogenation can furnish partially/fully saturated analogs (dihydro/tetrahydropyrazines, piperazines) for property modulation.
Cross‑coupling via halogenated analogs: While this substrate is not halogenated, analogous halo‑pyrazines participate in Suzuki, Buchwald–Hartwig, and Negishi chemistry. Your intermediate derived from this compound can be halogenated at benzylic or ring positions for entry into these manifolds.
Practical notes
Protect ring integrity by avoiding strong mineral acids at elevated temperature unless salt formation is desired; protonation can dramatically alter solubility and reactivity.
For photochemical or radical processes, control oxygen and light exposure to limit over‑oxidation.
Target Specificity
Not applicable to this product class. This is a small‑molecule heteroaromatic reagent/standard, not a biological affinity reagent or antibody. No antigen/epitope specificity, clone, isotype, or species reactivity is relevant.
Perguntas frequentes
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 29460-92-2, the molecular formula is C8H12N2, and the molecular weight is 136.190 g/mol. InChIKey YAIMUUJMEBJXAA-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.
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