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CS-W001157 4
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Methyl 2-cyano-2-methylpropanoate

  • CAS No. 72291-30-6

  • Cat. No. CS-0028771
  • Purity≥98%
  • MDL No.MFCD03428328

*For research and further manufacturing use only, not for direct human use.

Methyl 2-cyano-2-methylpropanoate|CS-0028771

Structure of 72291-30-6

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General Information

  • CAS No. 72291-30-6
  • Cat. No. CS-0028771
  • Purity ≥98%
  • MDL No. MFCD03428328
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₉NO₂
  • Molecular Weight 127.14
  • Synonym(s) 2,2-Dimethyl-2-cyanoacetic acid methyl ester; 2-Cyano-2,2-dimethylacetic acid methyl ester; 2,2-DIMETHYLCYANOACETATE METHYL ESTER
  • SMILES CC(C)(C#N)C(OC)=O

Description

Methyl 2-cyano-2-methylpropanoate features a sterically hindered α,α-dimethyl ester group flanked by a nitrile functionality, enabling robust participation in Michael additions and multicomponent couplings. This bench-stable reagent integrates efficiently into synthetic sequences requiring controlled carbon–carbon bond formation under mild conditions.

Application

Methyl 2-cyano-2-methylpropanoate serves as a robust building block in synthetic organic chemistry, enabling efficient access to sterically hindered nitriles and α-amino nitriles via nucleophilic addition reactions. Its tert-butyl-like steric profile enhances stability under basic conditions and facilitates straightforward purification. The molecule functions effectively in Michael additions, Mannich-type reactions, and as a precursor to heterocyclic scaffolds including pyrrolidines and imidazoles.

Synthesis

  • Route1
    • In-stock
      Methyl 2-cyanoacetate|CS-W016657
      105-34-0
    • null|null
      74-88-4
    • ~71%
    • In-stock
      Methyl 2-cyano-2-methylpropanoate|CS-0028771
      72291-30-6

    References

    • Nippon Steel Corporation; Nippon Steel Chemical Co., Ltd. Patent: US5866592 A1, 1999 ;
  • Route2
    • null|null
      105-56-6
    • null|null
      77-78-1
    • ~%
    • In-stock
      Ethyl 2-cyano-2-methylpropanoate|CS-0096411
      1572-98-1
    • In-stock
      Methyl 2-cyano-2-methylpropanoate|CS-0028771
      72291-30-6

    References

    • WO2012/21446 A2, ; Page/Page column 29 ;
  • Route3
    • null|null
      74-87-3
    • In-stock
      Methyl 2-cyanoacetate|CS-W016657
      105-34-0
    • ~%
    • In-stock
      Methyl 2-cyano-2-methylpropanoate|CS-0028771
      72291-30-6

    References

    • WO2010/112482 A1, ; Page/Page column 27 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H302+H312+H332-H315-H319
Precautionary Statements : P210-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P370+P378-P403-P501

Quality Control

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Computational Chemistry Data

  • TPSA   50.09
  • LogP   0.70918
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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