Monoethyl itaconate

Name: Monoethyl itaconate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 57718-07-7
Cat. No. CS-0112955
Purity≥98%
MDL No.MFCD00059138

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 57718-07-7

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General Information

CAS No. 57718-07-7
Cat. No. CS-0112955
Purity ≥98%
MDL No. MFCD00059138
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₁₀O₄
Molecular Weight 158.15
Synonym(s) None
SMILES C=C(CC(OCC)=O)C(O)=O

Description

Monoethyl itaconate features a reactive maleimide-like double bond flanked by electron-withdrawing ester and carboxylate groups, enabling efficient bioconjugation under physiological conditions. This bench-stable derivative integrates readily into peptide and protein labeling workflows, offering high selectivity for cysteine residues without requiring toxic catalysts.

Application

Monoethyl itaconate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized succinate derivatives and heterocyclic scaffolds. Its ester and carboxylic acid functionalities offer orthogonal reactivity for conjugation, amidation, and cycloaddition reactions. The molecule exhibits excellent bench stability, facilitates straightforward purification, and functions effectively in standard coupling protocols and multistep syntheses relevant to medicinal chemistry and process development workflows.

Synthesis

Route1
- 64-17-5
- In-stock
  
  97-65-4
- ~99%
- In-stock
  
  57718-07-7
References
- Rama Devi; Rajaram Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000 , vol. 39, # 4 p. 294 - 296
Route2
- 64-17-5
- In-stock
  
  97-65-4
- ~97%
- In-stock
  
  57718-07-7
- In-stock
  
  2409-52-1
References
- Organic Letters, , vol. 13, # 8 p. 1932 - 1935
Route3
- 64-17-5
- In-stock
  
  2170-03-8
- ~58%
- In-stock
  
  57718-07-7
References
- Ferraboschi, Patrizia; Casati, Silvana; Grisenti, Paride; Santaniello, Enzo Tetrahedron, 1994 , vol. 50, # 10 p. 3251 - 3258

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 63.6
LogP 0.5804
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Skeleton Fatty chain compounds

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Olefins

Building Blocks Functional Group Ester

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Monoethyl itaconate

CAS No. 57718-07-7

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