Cas no 1444-05-9 (Diethyl Bis(2-cyanoethyl)malonate)

Diethyl Bis(2-cyanoethyl)malonate is a versatile chemical intermediate primarily used in organic synthesis and pharmaceutical applications. Its structure, featuring two cyanoethyl groups and an active malonate ester, makes it a valuable precursor for constructing complex molecules, particularly in the synthesis of heterocycles and functionalized malonates. The compound's reactivity allows for efficient nucleophilic substitutions and cyclization reactions, enabling the formation of carbon-carbon and carbon-nitrogen bonds. Its stability under standard conditions and compatibility with various reaction conditions enhance its utility in multistep syntheses. The presence of both ester and nitrile functionalities provides flexibility for further derivatization, making it a useful building block in medicinal chemistry and material science.
Diethyl Bis(2-cyanoethyl)malonate structure
1444-05-9 structure
Product Name:Diethyl Bis(2-cyanoethyl)malonate
CAS No:1444-05-9
MF:C13H18N2O4
MW:266.293023586273
CID:83675
PubChem ID:74046
Update Time:2025-05-25

Diethyl Bis(2-cyanoethyl)malonate Chemical and Physical Properties

Names and Identifiers

    • Diethyl 2,2-bis(2-cyanoethyl)malonate
    • 4,4-Dicarbethoxypimelonitrile
    • Bis(2-cyanoethyl)malonic acid diethyl ester~Bis(4,4-ethoxycarbonyl)pimelonitrile
    • Diethyl bis(2-cyanoethyl)malonate
    • Propanedioic acid, 2,2-bis(2-cyanoethyl)-, 1,3-diethyl ester
    • diethyl 2,2-bis(2-cyanoethyl)propanedioate
    • DIETHYL BIS-(2-CYANOETHYL)-MALONATE
    • FT-0617032
    • EN300-129248
    • AI3-13041
    • NSC-3669
    • MLS000104225
    • 4,4-DICARBETHOXYPIMELODINITRILE
    • SR-01000408042
    • AKOS005206989
    • 1,3-diethyl 2,2-bis(2-cyanoethyl)propanedioate
    • CHEMBL1524071
    • DTXSID90932301
    • SCHEMBL1341844
    • NSC 3669
    • SR-01000408042-1
    • HMS2410B16
    • Z1624134471
    • EINECS 215-886-6
    • CS-0308727
    • 1444-05-9
    • NSC3669
    • Propanedioic acid, bis(2-cyanoethyl)-, diethyl ester
    • SMR000051274
    • NS00045341
    • diethyl bis(2-cyanoethyl)propanedioate
    • DB-042732
    • STK831912
    • Diethyl Bis(2-cyanoethyl)malonate
    • MDL: MFCD00013831
    • Inchi: 1S/C13H18N2O4/c1-3-18-11(16)13(7-5-9-14,8-6-10-15)12(17)19-4-2/h3-8H2,1-2H3
    • InChI Key: KAESGTBHXNCAHO-UHFFFAOYSA-N
    • SMILES: O(CC)C(C(C(=O)OCC)(CCC#N)CCC#N)=O
    • BRN: 1800053

Computed Properties

  • Exact Mass: 266.12700
  • Monoisotopic Mass: 266.127
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 10
  • Complexity: 373
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 0.8
  • Topological Polar Surface Area: 100A^2

Experimental Properties

  • Color/Form: crystal
  • Density: 1.124
  • Melting Point: 60-63°C
  • Boiling Point: 174-176°C 0,5mm
  • Flash Point: 174-176°C/0.5mm
  • Refractive Index: 1.466
  • PSA: 100.18000
  • LogP: 1.70656
  • Solubility: Insoluble

Diethyl Bis(2-cyanoethyl)malonate Security Information

  • Hazardous Material transportation number:3276
  • Hazard Category Code: 20/21
  • Safety Instruction: S22-S36/37/39
  • Packing Group:III
  • Hazard Level:6.1
  • Safety Term:6.1
  • Packing Group:III
  • Risk Phrases:R20/21/22
  • HazardClass:6.1
  • PackingGroup:III
  • TSCA:Yes

Diethyl Bis(2-cyanoethyl)malonate Customs Data

  • HS CODE:2926909090
  • Customs Data:

    China Customs Code:

    2926909090

    Overview:

    2926909090 Other nitrile based compounds. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Diethyl Bis(2-cyanoethyl)malonate Pricemore >>

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Diethyl Bis(2-cyanoethyl)malonate Production Method

Additional information on Diethyl Bis(2-cyanoethyl)malonate

Recent Advances in the Application of Diethyl Bis(2-cyanoethyl)malonate (CAS: 1444-05-9) in Chemical Biology and Pharmaceutical Research

Diethyl Bis(2-cyanoethyl)malonate (CAS: 1444-05-9) is a versatile chemical intermediate that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This compound, characterized by its malonate backbone and cyanoethyl functional groups, serves as a key building block in the synthesis of complex molecules, including heterocyclic compounds and bioactive agents. Recent studies have explored its utility in drug discovery, material science, and biocatalysis, highlighting its broad applicability and importance in advancing scientific research.

One of the most notable advancements involving Diethyl Bis(2-cyanoethyl)malonate is its role in the synthesis of novel heterocyclic compounds. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its use as a precursor in the development of pyridine and pyrimidine derivatives, which exhibit promising antimicrobial and anticancer activities. The researchers employed a multi-step synthetic route, leveraging the reactivity of the cyanoethyl groups to facilitate cyclization reactions. The resulting compounds showed significant inhibitory effects against a panel of bacterial strains and cancer cell lines, underscoring the potential of Diethyl Bis(2-cyanoethyl)malonate in medicinal chemistry.

In addition to its applications in drug discovery, Diethyl Bis(2-cyanoethyl)malonate has been investigated for its role in material science. A recent report in Advanced Materials highlighted its use as a crosslinking agent in the fabrication of biodegradable polymers. The study revealed that the incorporation of this compound into polymer matrices enhanced mechanical strength and thermal stability while maintaining biocompatibility. These findings suggest potential applications in biomedical engineering, such as the development of drug delivery systems and tissue scaffolds.

Furthermore, biocatalytic transformations involving Diethyl Bis(2-cyanoethyl)malonate have been explored to achieve greener and more sustainable synthetic processes. A 2022 publication in ACS Catalysis described the enzymatic hydrolysis of this compound using engineered lipases, yielding high-value chiral intermediates with excellent enantioselectivity. This approach not only reduces the reliance on traditional chemical catalysts but also aligns with the growing demand for environmentally friendly synthetic methodologies in the pharmaceutical industry.

Despite these promising developments, challenges remain in the large-scale production and application of Diethyl Bis(2-cyanoethyl)malonate. Issues such as cost-effectiveness, scalability, and regulatory compliance need to be addressed to fully realize its potential. Ongoing research efforts are focused on optimizing synthetic routes, improving yield, and exploring new applications in emerging fields such as nanotechnology and agrochemicals.

In conclusion, Diethyl Bis(2-cyanoethyl)malonate (CAS: 1444-05-9) continues to be a valuable tool in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate, coupled with recent advancements in drug discovery, material science, and biocatalysis, positions it as a compound of significant interest. Future studies are expected to further elucidate its potential and address existing challenges, paving the way for innovative applications in science and industry.

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