Bis(2,5-dioxopyrrolidin-1-yl) heptanedioate

Name: Bis(2,5-dioxopyrrolidin-1-yl) heptanedioate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 74648-14-9
Cat. No. CS-0524101
Purity≥98%
MDL No.MFCD01318519

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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+

An item is classified as a dangerous good if our website displays Hazardous Material (HazMat) information for it.

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Bis(2,5-dioxopyrrolidin-1-yl) heptanedioate|CS-0524101

Structure of 74648-14-9

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General Information

CAS No. 74648-14-9
Cat. No. CS-0524101
Purity ≥98%
MDL No. MFCD01318519
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₈N₂O₈
Molecular Weight 354.32
Synonym(s) None
SMILES O=C(ON1C(=O)CCC1=O)CCCCCC(=O)ON2C(=O)CCC2=O

Description

Bis(2,5-dioxopyrrolidin-1-yl) heptanedioate is a bifunctional acylating agent featuring two pyrrolidinone-derived leaving groups. This reagent enables efficient coupling of carboxylic acid functionalities in peptide synthesis and polymer chemistry. The heptanedioate spacer provides optimal chain length for bridging reactive sites, enhancing solubility and reaction kinetics under standard conditions.

Application

Bis(2,5-dioxopyrrolidin-1-yl) heptanedioate serves as a stable, bench-ready active ester derivative enabling efficient amide bond formation under mild conditions. Its seven-carbon spacer provides optimal flexibility for coupling amino acids and other carboxylic acid-containing building blocks in peptide synthesis and macrocycle construction. The pyrrolidinone leaving groups facilitate clean reaction progress with minimal racemization, while the compound’s crystalline nature supports straightforward handling and purification—ideal for iterative synthetic workflows in medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  6066-82-6
- In-stock
  
  111-16-0
- ~99%
- In-stock
  
  74648-14-9
References
- Kaufmann, Gunnar F.; Sartorio, Rafaella; Lee, Sang-Hyeup; Mee, Jenny M.; Altobell III, Laurence J.; Kujawa, David P.; Jeffries, Emily; Clapham, Bruce; Meijler, Michael M.; Janda, Kim D. Journal of the American Chemical Society, 2006 , vol. 128, # 9 p. 2802 - 2803
Route2
- In-stock
  
  6066-82-6
- In-stock
  
  142-79-0
- ~91%
- In-stock
  
  74648-14-9
References
- Hasinoff, Brian B.; Zhang, Rui; Wu, Xing; Guziec, Lynn J.; Guziec Jr., Frank S.; Marshall, Kyle; Yalowich, Jack C. Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 13 p. 4575 - 4582

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

TPSA 127.36
LogP 0.1513
H_Acceptors 8
H_Donors 0
Rotatable_Bonds 8

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Biochemistry Biochemicals and Reagents Bioconjugation Homobifunctional Cross-Linkers

Chemical Biology Pharmaceutical Development and Drug Discovery Research Bioconjugation Homobifunctional Cross-Linkers

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Linkers and Crosslinkers Homobifunctional Cross-Linkers

Chemical Biology Pharmaceutical Development and Drug Discovery Research Linkers and Crosslinkers Homobifunctional Cross-Linkers

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Bis(2,5-dioxopyrrolidin-1-yl) heptanedioate

CAS No. 74648-14-9

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