技术文章

N,N,N',N'-Tetramethylsuccinamide: Properties, Uses & Handling Guide

N,N,N',N'-Tetramethylsuccinamide is a symmetrical N,N,N',N'-tetrasubstituted succinic acid diamide that serves as a versatile polar aprotic-like reagent and intermediate in organic synthesis and research applications.

Chemical Name
N,N,N',N'-Tetramethylsuccinamide
Molecular Formula
C8H16N2O2
Molecular Weight
172.23 g/mol
Functional Class
Diamide (bis-tertiary amide)
Aladdin SKU
N693797
Appearance
White to off-white solid or crystalline powder (typical for this class)

Chemical Identity and Physical Properties

N,N,N',N'-Tetramethylsuccinamide (CAS not confirmed in source material; see review flags) is the fully N-methylated diamide of succinic acid. Its molecular formula is C8H16N2O2, giving a molecular weight of 172.23 g/mol. The compound features two tertiary amide bonds, which confer high chemical stability toward hydrolysis under neutral conditions and impart a degree of polarity comparable to other N,N-disubstituted amides.

The symmetrical structure means no chiral center is present. The two carbonyl groups are electronically equivalent, making the molecule suitable as a bidentate ligand or chelating agent in certain coordination chemistry contexts. Its solubility profile is expected to include good dissolution in polar organic solvents such as DMSO, DMF, and acetonitrile, as well as moderate solubility in water, though precise solubility data should be confirmed from the product specification sheet.

Synthesis and Preparation

N,N,N',N'-Tetramethylsuccinamide is typically prepared by the reaction of succinic acid or succinic anhydride with dimethylamine, or by the acylation of dimethylamine with succinyl chloride under controlled conditions. Standard diamide synthesis protocols involve careful temperature control and removal of water or HCl byproducts to drive the reaction to completion.

Researchers should verify the exact synthetic route and purity specifications on the Aladdin product datasheet for lot-specific information. The reagent supplied by Aladdin (SKU: N693797) is intended for research use and has been characterized for identity and purity; consult the certificate of analysis (CoA) for quantitative purity data before use in sensitive applications.

Research Applications

As a stable, symmetric bis-tertiary amide, N,N,N',N'-Tetramethylsuccinamide finds utility across several domains of chemical research:

  • Organic synthesis intermediate: The compound can serve as a building block or protecting-group equivalent in multi-step syntheses where selective functionalization of one amide over the other is not required.
  • Coordination chemistry: The two carbonyl oxygen atoms may coordinate to metal centers, making it a candidate ligand for exploratory metal-complex studies.
  • Model compound studies: Due to its well-defined symmetry and lack of interfering functional groups, it is useful as a model compound in spectroscopic (IR, NMR) calibration or mechanistic investigations of amide bond behavior.
  • Solvent or co-solvent candidate: Structurally analogous to established polar aprotic solvents (e.g., NMP, DMF), N,N,N',N'-Tetramethylsuccinamide may be evaluated as a greener or alternative solvent medium in exploratory solubility and reaction-medium studies.

All proposed applications should be validated by the end user under laboratory-specific conditions.

Safe Handling, Storage, and Disposal

Handling: Use standard laboratory personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a lab coat when handling N,N,N',N'-Tetramethylsuccinamide. Work in a well-ventilated area or fume hood to minimize inhalation of dust or vapors. Avoid contact with skin, eyes, and mucous membranes.

Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from incompatible materials such as strong oxidizers and strong acids. Specific storage temperature recommendations should be confirmed from the product label and Safety Data Sheet (SDS) available from Aladdin Scientific.

Disposal: Dispose of this compound and contaminated materials in accordance with applicable local, regional, and national regulations for chemical waste. Do not pour down the drain without verification of local discharge limits. Consult your institution's Environmental Health and Safety (EHS) office for guidance.

Emergency measures: In case of skin or eye contact, flush immediately with copious water for at least 15 minutes and seek medical attention if irritation persists. Refer to the Aladdin SDS for complete first-aid and emergency response information.

Ordering and Quality Information

N,N,N',N'-Tetramethylsuccinamide is available from Aladdin Scientific under SKU N693797. Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity and purity. Researchers are encouraged to review the CoA and the corresponding SDS prior to use.

For bulk quantities, custom packaging, or technical support, contact Aladdin Scientific's customer service team. All products are intended for research use only and are not suitable for diagnostic, therapeutic, food, agricultural, or household applications unless explicitly stated.

Place orders through the Aladdin Scientific website or authorized distributors. Refer to the current product page for pricing, available package sizes, and lead times.

Frequently asked questions

What is N,N,N',N'-Tetramethylsuccinamide used for in research?

N,N,N',N'-Tetramethylsuccinamide is used as an organic synthesis intermediate, a model compound for spectroscopic and mechanistic studies of amide bonds, and a candidate ligand in coordination chemistry. It may also be evaluated as an alternative polar solvent medium in exploratory reaction studies.

How should N,N,N',N'-Tetramethylsuccinamide be stored?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from strong oxidizers and strong acids. Consult the Aladdin Scientific Safety Data Sheet and product label for lot-specific storage temperature recommendations.

What personal protective equipment is recommended when handling this compound?

Use chemical-resistant gloves, safety goggles, and a laboratory coat as a minimum when handling N,N,N',N'-Tetramethylsuccinamide. Working in a well-ventilated fume hood is recommended to avoid inhalation of dust or vapors.

Where can I find the Certificate of Analysis (CoA) for Aladdin's N,N,N',N'-Tetramethylsuccinamide?

The Certificate of Analysis for SKU N693797 is available on the Aladdin Scientific product page. You can access it by entering the lot number on the website, or by contacting Aladdin Scientific customer service directly.

References

  1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for amide chemistry and diamide synthesis.
  2. Aladdin Scientific. Product datasheet and Safety Data Sheet for N,N,N',N'-Tetramethylsuccinamide, SKU N693797. Aladdin Scientific Corp.

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

目录: 技术文章

Da — 若无特别说明,分子量单位默认为道尔顿。   Mw — 重均分子量。   Mn — 数均分子量。

产品仅供科研与开发使用,不用于人体、动物、诊断或治疗。

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阿拉丁科学.《N,N,N',N'-Tetramethylsuccinamide: Properties, Uses & Handling Guide》. 阿拉丁知识库,更新于 2026年10月3日。 https://www.aladdin-e.com/zh_cn/faqs/nn-nn-tetramethylsuccinamide-properties-uses-handling-guide-en.html
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