N-Hydroxymethyl succinimide

Name: N-Hydroxymethyl succinimide
Brand: ChemScene
Availability: InStock
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CAS No. 5146-68-9
Cat. No. CS-0217538
Purity≥97%
MDL No.MFCD01328751

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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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Structure of 5146-68-9

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General Information

CAS No. 5146-68-9
Cat. No. CS-0217538
Purity ≥97%
MDL No. MFCD01328751
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₇NO₃
Molecular Weight 129.11
Synonym(s) N-Methylolsuccinimide
SMILES C1CC(=O)N(CO)C1=O

Description

1-(Hydroxymethyl)pyrrolidine-2,5-dione features a reactive hydroxymethyl group tethered to a pyrrolidine-2,5-dione core, enabling direct conjugation in synthetic workflows. This scaffold integrates readily into peptide and small-molecule architectures, offering enhanced solubility and metabolic stability under standard conditions.

Application

1-(Hydroxymethyl)pyrrolidine-2,5-dione serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized heterocycles and peptide analogs. The pendant hydroxymethyl group provides a handle for selective derivatization, while the pyrrolidinedione core offers stability and compatibility with standard coupling and protection protocols. Its bench-stable nature and broad functional group tolerance facilitate integration into multi-step syntheses, particularly in medicinal chemistry and natural product synthesis workflows.

Synthesis

Route1
- In-stock
  
  123-56-8
- 50-00-0
- ~60%
- In-stock
  
  5146-68-9
References
- Mahfouz, Nadia M.; Omar, Farghaly A.; Aboul-Fadl, Tarek European Journal of Medicinal Chemistry, 1999 , vol. 34, # 7-8 p. 551 - 562
Route2
- 50680-64-3
- ~%
- In-stock
  
  5146-68-9
- 98021-28-4
References
- Kissinger; Ungnade Journal of Organic Chemistry, 1958 , vol. 23, p. 815,818

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-H302-H335
Precautionary Statements : P260-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 57.61
LogP -0.9148
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Key Words

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N-Hydroxymethyl succinimide

CAS No. 5146-68-9

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