This compound belongs to the class of organic compounds known as nitriles. These are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
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 tested bioassay or analytical protocols are provided for this item. As a general chemical building block, usage protocols depend on the intended synthetic transformation. For representative procedures, consult literature for:
Alkene hydroboration–oxidation sequences on terminal alkenes bearing nitriles.
Heterogeneous hydrogenation of aliphatic dinitriles to diamines.
Radical thiol–ene additions under photochemical conditions.
For any specific application, perform small-scale trials to optimize stoichiometry, solvent, temperature, and purification, and consult the SDS for safe handling.
Biological Roles
This product is a synthetic organic building block and is not a biological metabolite or cofactor.
General notes (contextual, not item-specific)
Aliphatic dinitriles are not common endogenous metabolites in primary metabolism. They may be used in chemical biology as reactive handles: the terminal alkene can participate in radical additions (e.g., thiol–ene) for surface or biomolecule modification under controlled conditions.
The nitrile functional group is sometimes used in medicinal chemistry as a bioisostere for carbonyl-derived functions, but 2-methyleneglutaronitrile itself is primarily a feedstock/intermediate rather than a probe.
Biocompatibility considerations
Nitriles and their vapors can be irritating and potentially toxic; experiments involving cells or proteins should ensure exhaustive removal of the reagent and solvents prior to biological testing.
Enzymatic relevance
Enzymatic transformations of aliphatic dinitriles (e.g., nitrilases or nitrile hydratases) are known in biocatalysis to produce acids or amides; such approaches could, in principle, be applied to this substrate to form diacids/diamides under mild conditions.
No specific biological role, pathway involvement, or receptor interaction is assigned to this compound.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare aqueous buffer systems. As a hydrophobic aliphatic dinitrile with a terminal alkene, it lacks acid/base conjugate pairs in the physiological pH range that would confer buffering capacity.
For aqueous laboratory work, use conventional buffers (e.g., phosphate, HEPES, Tris) and consult their respective preparation guidelines.
Green Alternatives
Selecting greener options involves solvent and process intensification choices rather than replacing the reagent itself (which is the desired building block). Consider the following to improve sustainability when working with 2-methyleneglutaronitrile.
Greener solvent choices (general guidance)
Prefer 2-MeTHF or CPME over THF/Et2O for hydroborations and radical additions; they are less volatile and can be sourced from biomass.
Use ethanol or isopropanol as hydrogenation media when compatible with the catalyst, reducing reliance on chlorinated solvents.
Replace DMF/DMSO with propylene carbonate or MeOAc where kinetics permit.
Energy and safety
Continuous-flow hydrogenation can reduce solvent volumes and improve heat/mass transfer, enabling lower catalyst loadings.
Photocatalytic thiol–ene reactions under visible light may proceed at ambient temperature, reducing energy input.
Waste minimization
Apply telescoped sequences: e.g., alkene hydroboration followed by oxidative workup without isolation, then nitrile transformation, minimizing solvent exchanges.
Recycle catalysts/supports (Ni, Co on reusable supports) and employ aqueous workups that allow phase separation and solvent recovery.
Comparison snapshot (general)
Parameter | Conventional choice | Greener alternative | Trade-offs
Hydrogenation solvent | THF/MeOH | EtOH/i-PrOH or water/ethanol mixtures | Catalyst solubility may change; rate can drop.
Ether solvent | THF | 2-MeTHF/CPME | Slightly different polarity; need peroxide monitoring reduced.
Implement LCA-driven selection where possible; tailor choices to catalyst compatibility and product isolation.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item.
General context (non-clinical)
2-Methyleneglutaronitrile can serve as a synthetic intermediate toward diamines, diacids, and heterocycles that may be used in process chemistry or materials connected to pharmaceutical manufacturing (e.g., ligands, resins, linkers).
The terminal alkene offers a handle for further derivatization (e.g., conjugation to polymers) before conversion of nitriles to amide/amine functionalities.
Regulatory note
This product is supplied for research use only. It is not intended for human or veterinary use, drug substance, or excipient applications without appropriate qualification and regulatory review.
For formulation-related applications, confirm residual solvents, stabilizers, and impurity profiles via CoA and perform risk assessments per ICH Q3A/Q3C/Q3D as applicable.
Physical Properties
Only limited item-specific physical data are provided for this catalog entry. The following are general/literature values for 2-methyleneglutaronitrile and are NOT item specifications.
Item-specific (from Product Data)
Appearance: 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 and computed properties (for reference)
Molecular formula (literature): C6H6N2
Molecular weight (literature): 106.12 g/mol
Physical state: typically a colorless to pale liquid (literature; may vary with purity and temperature).
Boiling point: literature values for related aliphatic dinitriles often lie in the 180–230 °C range; specific BP for 2-methyleneglutaronitrile should be verified from primary data (Not specified for this item; refer to CoA/Spec Sheet).
Density (20–25 °C): Not specified for this item; refer to CoA/Spec Sheet.
Refractive index (nD): Not specified for this item; refer to CoA/Spec Sheet.
Solubility: expected low solubility in water; miscible with many organic solvents (e.g., ethers, chlorinated solvents, aromatics) — literature expectations; measure for your system.
LogP (estimated): aliphatic dinitriles with a terminal alkene typically show moderate hydrophobicity; consult cheminformatics tools for a precise value.
Vapor pressure: anticipated low at RT relative to light mono-nitriles; confirm before scale-up.
Note: For method validation, chromatography, or engineering calculations, confirm properties on the Certificate of Analysis (CoA) or SDS.
Quality and Grades
Item-specific quality information (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research grade: suitable for most synthetic and development workflows; impurities are typically controlled but may not meet stringent analytical or GMP thresholds.
Purification-sensitive uses (e.g., polymerization studies, fine catalysis, or trace analysis) may require additional purification or specific specifications such as low acid content, water content (Karl Fischer), peroxides, and UV absorbance windows. Since these are not specified here, confirm via CoA.
Stabilizers/inhibitors
Unsaturated nitriles can be offered with or without polymerization inhibitors. No stabilizer information is provided for this item; verify on the CoA. If inhibitor-free, store under inert gas and protect from light/heat.
Batch-specific documentation
For exact assay, residual solvents, water, acidity/alkalinity, and elemental impurities: Not specified for this item; refer to CoA/Spec Sheet.
Suitability notes
If using for metal-catalyzed transformations (hydrogenation, cross-coupling onto the alkene, hydrosilylation), trace metal and sulfur content in the reagent is usually not critical, but solvent and peroxide content can impact outcomes; test and condition accordingly.
For regulated or high-spec applications, request detailed specifications and analytical data for the exact lot.
Reaction and Applications
2-Methyleneglutaronitrile is a bifunctional synthon that combines a terminal alkene and two nitriles, enabling orthogonal or tandem transformations.
Transformations of the alkene (general/literature)
Hydrofunctionalizations: hydroboration–oxidation to give secondary alcohols distal to nitriles; hydrosilylation to access silyl intermediates; hydroazidation or radical additions (thiol–ene) to introduce heteroatoms.
Oxidations: Wacker-type oxidation (Pd) can furnish ketone/aldehyde motifs adjacent to the nitrile-bearing chain (substrate and directing effects to be evaluated).
Cycloadditions: Radical and pericyclic additions to the terminal alkene can build cyclic frameworks, with nitriles serving as latent amide/amine handles.
Transformations of the nitriles (general/literature)
Hydrogenation to diamines (Raney Ni, Co, or Pd catalysts; H2 pressure) yielding 1,5-diamines after reduction; the alkene may be reduced concurrently to a saturated chain.
Hydrolysis to diacids or diamides under acidic or basic conditions; stepwise partial conversions afford amides/esters.
Organometallic additions (RMgX, RLi) to form imines/ketimines that can be hydrolyzed to ketones/aldehydes upon workup.
Tandem and orthogonal strategies
Protect/reduce nitriles first, then functionalize the alkene, or vice versa, depending on catalyst tolerance. For example, selective hydroboration of the alkene in the presence of relatively inert nitriles, followed by nitrile reduction.
Use cases in synthesis (literature examples)
Precursor to specialty diamines, diacids, or amino alcohols for polymer, ligand, or material applications.
Intermediate for installing side chains where terminal alkene enables tagging or crosslinking, while nitriles provide latent functionality.
Note: Optimize conditions to prevent undesired polymerization or over-reduction; catalyst choice and solvent profoundly affect chemoselectivity.
Reaction Conditions
The following are general literature-level guidance for common transformations of 2-methyleneglutaronitrile; they are not item-specific specifications. Optimize and validate for your system.
Alkene hydroboration–oxidation
Typical: 9-BBN (1.1–1.3 equiv) in THF or 2-MeTHF, 0–25 °C, 1–3 h; oxidative workup with H2O2/NaOH (aq). Secondary alcohols formed adjacent to the alkene insertion site. Nitriles are generally tolerated.
Radical thiol–ene addition
Conditions: photoinitiator (e.g., DMPA, 1–2 mol%) or UV/blue-light photocatalyst; solvent toluene/CPME; 20–30 °C; 0.5–2 h. Oxygen exclusion improves yields; monitor for any unintended polymerization.
Nitrile hydrogenation to primary amines
Heterogeneous catalysts: Raney Ni, Co, or Pd/C; solvent EtOH, i-PrOH, or THF; H2 10–60 bar; 25–120 °C; 2–16 h. Alkene typically hydrogenates under these conditions, giving saturated 1,5-diamines. For alkene retention, explore chemoselective catalysts (e.g., Co-based with additives) and lower pressures/temps.
Nitrile hydrolysis
Acidic: conc. H2SO4 or HCl, reflux to 100–120 °C, hours to overnight, yielding diamides/diacids depending on conditions.
Basic: NaOH/KOH in aqueous alcohol, reflux; often requires co-solvent to solubilize substrate.
Organometallic additions
RMgX or RLi (1.1–2.0 equiv per nitrile) in ether solvents at −78 to 0 °C; quench then hydrolyze imines to ketones. Protect alkene if necessary to avoid side reactions under strongly basic/nucleophilic conditions.
Purification
Due to polarity from dinitriles, use gradient normal-phase chromatography or switch to reverse-phase if needed; distillation may be feasible but verify thermal stability.
Safety and Handling
Item-specific hazard classifications are not provided in the Product Data. Always consult the SDS for authoritative information.
GHS/CLP classification
Signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
General hazards for aliphatic dinitriles with terminal alkenes (literature/general)
May be harmful if swallowed, inhaled, or in contact with skin; nitriles can release toxic species under combustion.
Liquid can be irritating to skin/eyes; avoid vapor exposure in poorly ventilated areas.
Combustible; keep away from ignition sources. Nitriles may form hazardous cyanide-containing decomposition products when burned.
Work in a fume hood; avoid inhalation of vapors/aerosols.
Wear appropriate PPE: lab coat, safety glasses or face shield, and chemically resistant gloves (e.g., nitrile gloves; change regularly).
Prevent contact with strong acids/bases and strong oxidizers; avoid strong nucleophiles or acids that could induce polymerization or hydrolysis.
If the material is inhibitor-free, unsaturated systems can, in rare cases, polymerize under radical initiation; minimize exposure to heat, light, and peroxides.
First-aid overview (general)
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; get medical advice if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire response
Use dry chemical, CO2, or alcohol-resistant foam. Fire may produce CO, CO2, NOx, and HCN.
Spill response
Absorb with inert material, collect in chemical waste; ventilate area; avoid ignition sources.
Solvent Selection
As a low-to-moderate polarity aliphatic dinitrile bearing a terminal alkene, 2-methyleneglutaronitrile is typically handled in common organic media. No item-specific solubility data are provided.
General solubility/miscibility (literature expectations)
Likely low solubility in water; soluble in ethers (THF, MTBE), chlorinated solvents (DCM, chloroform), aromatics (toluene), and polar aprotics (MeCN, DMF, DMSO).
For moisture-sensitive steps (e.g., metal-catalyzed hydrogenation of nitriles), use anhydrous solvents.
Polarity and dielectric context (general)
The dinitrile motif increases dipolarity; however, the hydrophobic backbone and terminal alkene maintain good solubility in moderately polar organics.
Selection by application
Catalytic hydrogenation to diamines: alcohols (EtOH, i-PrOH) or polar aprotics (THF, MeOAc) are common; choose based on catalyst compatibility and workup.
Nucleophilic additions or Michael-type chemistry: polar aprotics (DMF, DMSO) can accelerate rates; dilute in toluene or THF for better handling and to moderate reactivity.
Radical thiol–ene or hydrosilylation: non-coordinating solvents (toluene, heptane) or ethers (CPME, THF) are typical.
Practical tips
Remove peroxides from ether solvents before long irradiations (photoinitiated additions).
If phase-transfer or biphasic hydrolysis is attempted, include a co-solvent to improve substrate solubility.
Comparison snapshot (general)
Versus adiponitrile: increased reactivity due to terminal alkene enables more diverse functionalization; slightly lower polarity aids solubility in nonpolar media.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data)
Storage conditions: Room temperature.
Shipped in: Normal.
General storage guidance for unsaturated dinitriles (good practice)
Keep container tightly closed in a cool, well-ventilated place. Protect from heat and direct sunlight.
If supplied without inhibitor, consider storing under inert gas (nitrogen/argon) to minimize potential radical-initiated reactions; avoid contact with peroxides.
Segregate from strong oxidizers, strong acids/bases, and strong nucleophiles.
Packaging/dispensing
Use amber glass where feasible to reduce light exposure. For air/moisture-sensitive operations, use septum caps and syringe/Schlenk techniques.
Reconstitution
Not applicable; product is typically used neat or dissolved directly in a compatible organic solvent. If crystals or precipitates form on cooling, gently warm to ambient and mix thoroughly before use.
Stability note
No item-specific stabilizer or shelf-life data are provided; refer to the CoA/Spec Sheet. Always check for purity by GC/LC/NMR before critical applications, especially after prolonged storage.
Research Use Note
For research use only.
Structure and Identity
Intro: 2-Methyleneglutaronitrile is an aliphatic α-olefinic dinitrile, useful as a bifunctional building block where the combination of a terminal alkene and two terminal nitriles enables diverse downstream transformations.
Item-specific identifiers (from Product Data)
SKU: M132491
Product name: 2-Methyleneglutaronitrile
CAS: 1572-52-7
PubChem CID: 74080
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structure (general/literature description)
Core features: linear C5 backbone bearing nitrile groups at C1 and C5 (dinitrile), with an exocyclic terminal methylene at C2: an allylic terminal alkene flanked by methylene units leading to –C≡N termini.
Functional groups: two nitriles (–C≡N), one terminal alkene (–C(=CH2)–).
Saturation/unsaturation: one C=C and two cumulative C≡N units; no rings; no stereocenters.
Molecular descriptors (literature values, for reference only; not item specifications)
Representative InChIKey (literature): Not provided here; consult authoritative databases if needed.
2D structural description in words (general): From left to right, a terminal nitrile carbon is attached to a methylene (–CH2–), which is bonded to a quaternary carbon bearing a terminal methylene substituent (–C(=CH2)–); this center is then connected to another methylene and finally to a terminal nitrile. The terminal methylene is not conjugated directly to the nitriles but is allylic to both.
Synthetic Utility
The synthetic value of 2-methyleneglutaronitrile lies in its orthogonal reactivity: a terminal alkene for rapid C–C/C–X installation and two nitriles as latent carbonyl/amine equivalents.
Functional group strategies
Alkene-first: Execute selective hydrofunctionalization (e.g., hydroboration–oxidation, halofunctionalization) to place functionality at C2/C3 positions without disturbing nitriles; subsequently reduce or hydrolyze nitriles to diamines/diacids.
Nitrile-first: Conduct chemoselective partial reduction (e.g., to imines/amines) or hydration to amides; then exploit the terminal alkene for tagging or crosslinking.
Named/typical reactions (literature)
Hydroboration–oxidation (BH3·THF, 9-BBN; H2O2/NaOH) to furnish secondary alcohols.
Hydrogenation of nitriles (Raney Ni, Co catalysts) to primary amines; concomitant alkene hydrogenation can saturate the backbone yielding 1,5-diamines.
Radical thiol–ene click to append thiols under photoinitiation.
Nucleophilic addition to nitriles (Grignard or organolithium) to form imines/ketimines, hydrolyzed to ketones.
Hydrolysis to diacids (H2SO4 aq, reflux) or to diamides (nitrile hydration; catalytic or enzymatic).
Retrosynthetic perspective
Serves as a masked 1,5-difunctional synthon allowing spacing control (five-atom tether) with a temporary terminal handle for site-selective installation.
Downstream value
Entry to diamines, diacids, amino alcohols, and cyclic derivatives relevant to polymer precursors, ligands, and specialty materials.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent. No antigen, epitope, species reactivity, clone, or isotype information applies.
Häufig gestellte Fragen
What is the purity of this product, and how is it determined?
This product is supplied at ≥98% purity, determined by gas chromatography (GC). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
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 1572-52-7, the molecular formula is C6H6N2, and the molecular weight is 106.13 g/mol. InChIKey NGCJVMZXRCLPRQ-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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