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2-(Dimethylamino)-2-methylpropanoic acid

  • CAS No. 220022-94-6

  • Cat. No. CS-0166674
  • Molecule weight131.17
  • Purity≥98%
  • MDL No.MFCD05230762

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

2-(Dimethylamino)-2-methylpropanoic acid|CS-0166674

Structure of 220022-94-6

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General Information

  • CAS No. 220022-94-6
  • Cat. No. CS-0166674
  • Purity ≥98%
  • MDL No. MFCD05230762
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₃NO₂
  • Molecular Weight 131.17
  • Synonym(s) Alanine, N,N,2-trimethyl- (9CI)
  • SMILES CC(C(O)=O)(C)N(C)C

Description

2-(Dimethylamino)-2-methylpropanoic acid features a sterically hindered tertiary carbon bearing both a carboxylic acid and a dimethylamino group, enabling robust nucleophilic reactivity. This structural motif delivers enhanced solubility in polar solvents and stability under standard bench conditions, making it ideal for use in peptide coupling and synthetic transformations requiring controlled basicity.

Application

2-(Dimethylamino)-2-methylpropanoic acid serves as a versatile building block in peptide synthesis and medicinal chemistry, offering a sterically hindered α-amino acid surrogate with enhanced solubility and stability. Its tertiary amine functionality enables facile salt formation and facilitates purification, while the carboxylic acid group supports standard coupling reactions. This compound functions effectively in solid-phase synthesis and is compatible with common protecting group strategies, making it a practical choice for constructing complex molecular architectures.

Synthesis

  • Route1
    • α-Aminoisobutyric acid|CS-0229297
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    • ~%
    • In-stock
      2-(Dimethylamino)-2-methylpropanoic acid|CS-0166674
      220022-94-6

    References

    • BASF Aktiengesellschaft Patent: US6143721 A1, 2000 ;
  • Route2
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      286011-63-0
    • ~%
    • In-stock
      2-(Dimethylamino)-2-methylpropanoic acid|CS-0166674
      220022-94-6

    References

    • Guerlavais, Vincent; Boeglin, Damien; Mousseaux, Delphine; Oiry, Catherine; Heitz, Annie; Deghenghi, Romano; Locatelli, Vittorio; Torsello, Antonio; Ghe, Corrado; Catapano, Filomena; Muccioli, Giampiero; Galleyrand, Jean-Claude; Fehrentz, Jean-Alain; Martinez, Jean Journal of Medicinal Chemistry, 2003 , vol. 46, # 7 p. 1191 - 1203
  • Route3

    References

    • Guerlavais, Vincent; Boeglin, Damien; Mousseaux, Delphine; Oiry, Catherine; Heitz, Annie; Deghenghi, Romano; Locatelli, Vittorio; Torsello, Antonio; Ghe, Corrado; Catapano, Filomena; Muccioli, Giampiero; Galleyrand, Jean-Claude; Fehrentz, Jean-Alain; Martinez, Jean Journal of Medicinal Chemistry, 2003 , vol. 46, # 7 p. 1191 - 1203

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   40.54
  • LogP   0.4112
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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