N,N,N',N'-Tetramethylsuccinamide: Properties & Lab Use FAQ

N,N,N',N'-Tetramethylsuccinamide is a symmetrical diamide derivative of succinic acid in which both terminal nitrogen atoms carry two methyl groups, conferring distinctive solubility and coordination properties that make it useful as a ligand precursor, solvent additive, and building block in organic synthesis.

Chemical Name

N,N,N',N'-Tetramethylsuccinamide

SKU / Catalog Number

N693797

Molecular Formula

C8H16N2O2

Molecular Weight

172.23 g/mol

Functional Class

Symmetrical disubstituted diamide (succinamide derivative)

Key Physical Property

Polar, water-miscible solid or low-melting solid; strong hydrogen-bond acceptor

What Is N,N,N',N'-Tetramethylsuccinamide and How Is It Structured?

N,N,N',N'-Tetramethylsuccinamide (CAS registry; MW 172.23 g/mol; molecular formula C₈H₁₆N₂O₂) is the fully N,N-dimethylated diamide of succinic acid. The molecule consists of a four-carbon backbone (–CH₂CH₂–) flanked on each end by a carbonyl group bearing a dimethylamino substituent. This symmetrical arrangement produces two equivalent amide bonds with pronounced resonance delocalization, making the carbonyl oxygens effective Lewis-basic coordination sites while simultaneously reducing the nitrogen nucleophilicity relative to unsubstituted amides.

Because neither nitrogen carries an N–H bond, the compound cannot act as a hydrogen-bond donor, but its two carbonyl oxygens are strong hydrogen-bond acceptors. This profile is analogous to other popular N,N-dimethylamide solvents and ligands (e.g., DMSO or HMPA analogues) and underlies many of its practical applications in the laboratory.

What Are the Typical Research and Synthetic Applications?

N,N,N',N'-Tetramethylsuccinamide serves several roles in synthetic and analytical chemistry:

• Bidentate ligand precursor: The two carbonyl oxygens can chelate metal ions, making the compound a candidate scaffold for coordination chemistry and catalysis studies.
• Polar aprotic additive: In reactions sensitive to hydrogen-bond donors, this diamide can act as a co-solvent or additive to modulate ion pairing and solvation, analogously to HMPA but without the associated toxicity profile of phosphoramides.
• Building block in organic synthesis: The activated amide bonds can be exploited in further functionalization, and the compound may serve as a starting material for the preparation of more elaborate diamide ligands or macrocyclic frameworks.
• Model compound in physical-organic studies: Its rigid yet flexible C4 backbone and well-defined electronic structure make it suitable for NMR conformational analysis, rotational barrier measurements around the amide bond, and solvation studies.

Researchers should verify suitability for specific applications by consulting primary literature, as the source material does not specify validated protocols.

How Should N,N,N',N'-Tetramethylsuccinamide Be Handled and Stored?

Although N,N,N',N'-Tetramethylsuccinamide is not classified among the most hazardous laboratory reagents, standard good laboratory practice (GLP) should always be observed:

• Personal protective equipment: Wear appropriate gloves, safety glasses, and a lab coat when handling the compound. Avoid inhalation of dust or aerosols.
• Storage: Store in a tightly closed container in a cool, dry, well-ventilated area, away from strong oxidizing agents and strong acids or bases that could hydrolyze the amide bonds. Typical ambient or refrigerated storage is appropriate; consult the product's Safety Data Sheet (SDS) for confirmed conditions.
• Disposal: Dispose of waste according to local, regional, and national regulations. Do not discharge into drains or waterways without treatment.
• Stability: Amide bonds are generally stable under neutral aqueous conditions but susceptible to hydrolysis under strongly acidic or basic conditions and at elevated temperatures.

Always consult the current SDS provided by Aladdin Scientific (SKU N693797) for authoritative hazard, handling, and storage information before use.

How to Order and What Specifications Are Available?

N,N,N',N'-Tetramethylsuccinamide is available from Aladdin Scientific under catalog number N693797. To place an order or inquire about available pack sizes, purity grades, and pricing, customers may:

• Visit the Aladdin Scientific website and search for SKU N693797.
• Contact the Aladdin Scientific sales or customer service team directly for bulk pricing, custom purity specifications, or institutional purchasing arrangements.
• Submit a purchase order through established procurement channels if your institution has an existing account.

Purity grade, available quantities, and current pricing should be confirmed at the time of ordering, as these details may vary. Researchers requiring a Certificate of Analysis (CoA) or additional quality documentation should request these from Aladdin Scientific customer support.

Frequently asked questions

What is the molecular formula and molecular weight of N,N,N',N'-Tetramethylsuccinamide?

N,N,N',N'-Tetramethylsuccinamide has the molecular formula C8H16N2O2 and a molecular weight of 172.23 g/mol. It is the fully N,N-dimethylated diamide of succinic acid.

Can N,N,N',N'-Tetramethylsuccinamide act as a hydrogen-bond donor in reactions?

No. Because all four nitrogen-bound hydrogen atoms have been replaced by methyl groups, the compound has no N–H bonds and therefore cannot act as a hydrogen-bond donor. However, its two carbonyl oxygens are strong hydrogen-bond acceptors, making it a useful polar aprotic-type additive in sensitive reactions.

Where can I find the Safety Data Sheet (SDS) for N,N,N',N'-Tetramethylsuccinamide (SKU N693797)?

The Safety Data Sheet for SKU N693797 is available directly from Aladdin Scientific. You can download it from the product page on the Aladdin Scientific website or request it from the customer service team. Always review the SDS before handling any chemical reagent.

Is N,N,N',N'-Tetramethylsuccinamide stable under aqueous conditions?

The amide bonds in N,N,N',N'-Tetramethylsuccinamide are generally stable under neutral aqueous conditions at ambient temperature. However, like most amides, the compound is susceptible to hydrolysis under strongly acidic or strongly basic conditions, particularly at elevated temperatures. Storage under recommended conditions and away from moisture is advised.

What catalog number should I use to order N,N,N',N'-Tetramethylsuccinamide from Aladdin Scientific?

The catalog number for N,N,N',N'-Tetramethylsuccinamide at Aladdin Scientific is N693797. Use this SKU when searching the website, placing orders, or contacting the sales team for pricing and availability.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference on amide bond properties and reactivity.
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. Reference on N,N-disubstituted amide electronic structure and hydrogen bonding.
3. Aladdin Scientific product page for N,N,N',N'-Tetramethylsuccinamide, SKU N693797. Aladdin Scientific, Shanghai.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.