N-(3,4-Dihydroxyphenethyl)methacrylamide

Name: N-(3,4-Dihydroxyphenethyl)methacrylamide
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CAS No. 471915-89-6
Cat. No. CS-0167925
Molecule weight221.26
Purity≥98%
MDL No.MFCD18816134

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N-(3,4-Dihydroxyphenethyl)methacrylamide|CS-0167925

Structure of 471915-89-6

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General Information

CAS No. 471915-89-6
Cat. No. CS-0167925
Purity ≥98%
MDL No. MFCD18816134
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₅NO₃
Molecular Weight 221.26
Synonym(s) N-[2-(3,4-Dihydroxyphenyl)ethyl]-2-methylacrylamide
SMILES C=C(C)C(NCCC1=CC=C(O)C(O)=C1)=O

Description

N-(3,4-Dihydroxyphenethyl)methacrylamide features a phenolic diol group flanked by an ethyl linker and a methacrylamide acrylate moiety. This dual functionality enables integration into polymer networks via radical polymerization while providing hydrophilic, metal-chelating sites for bioconjugation or surface functionalization. The molecule exhibits enhanced solubility in aqueous systems and stability under standard bench conditions.

Application

N-(3,4-Dihydroxyphenethyl)methacrylamide serves as a versatile building block for bioactive molecule synthesis, featuring a catechol moiety and acrylamide functionality. The ortho-dihydroxy group enables metal chelation and oxidation-sensitive transformations, while the methacrylamide side chain supports conjugate addition and polymerization reactions. Its stability under standard bench conditions facilitates purification and integration into diverse synthetic sequences, including peptide mimetics and heterocyclic scaffolds.

Synthesis

Route1
- In-stock
  
  62-31-7
- 920-46-7
- ~%
- In-stock
  
  471915-89-6
References
- Ham, Hyun Ok; Liu, Zhongqiang; Lau, K. H. Aaron; Lee, Haeshin; Messersmith, Phillip B. Angewandte Chemie - International Edition, 2011 , vol. 50, # 3 p. 732 - 736
Route2
- In-stock
  
  760-93-0
- In-stock
  
  62-31-7
- ~%
- In-stock
  
  471915-89-6
References
- Niu, Rui; Qiao, Jing; Yu, Hang; Nie, Jun; Yang, Dongzhi Frontiers of Chemistry in China, 2011 , vol. 6, # 3 p. 221 - 226

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+P364-P405-P501

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Computational Chemistry Data

TPSA 69.56
LogP 1.3326
H_Acceptors 3
H_Donors 3
Rotatable_Bonds 4

Key Words

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N-(3,4-Dihydroxyphenethyl)methacrylamide

CAS No. 471915-89-6

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