1-hydroxypyrrolidine-2,5-dione

• ChemBase ID: 85441
• Molecular Formular: C4H5NO3
• Molecular Mass: 115.0874
• Monoisotopic Mass: 115.02694303
• SMILES: N1(C(=O)CCC1=O)O
• Canonical SMILES: ON1C(=O)CCC1=O
• InChI: InChI=1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2
• InChIKey: NQTADLQHYWFPDB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-hydroxypyrrolidine-2,5-dione
• IUPAC Traditional name: 1-hydroxypyrrolidine-2,5-dione; N-hydroxysuccinimide
• Synonyms: N-Hydroxy-2,5-dioxopyrrolidine; 1-Hydroxysuccinimide; NSC 74335; N-Hydroxy-2,5-pyrrolidinedione; NHS; HOSu; N-HYDROXYSUCCINIMIDE; N-Hydroxysuccinimide; 1-Hydroxypyrrolidine-2,5-dione; 1-Hydroxy-2,5-pyrrolidinedione; N-Hydroxysuccinimide; 1-hydroxypyrrolidine-2,5-dione,HOSu; 1-羟基-2,5-吡咯烷二酮; N-羟基丁二酰亚胺

Database IDs

• CAS Number: 6066-82-6
• EC Number: 228-001-3
• MDL Number: MFCD00005516
• Beilstein Number: 113913
• PubChem SID: 162072557; 24880201; 24847975
• PubChem CID: 80170
• Chemspider ID: 72416
• Unique Ingredient Identifier: MJE3791M4T
• Wikipedia Title: N-Hydroxysuccinimide

CALCULATED PROPERTIES

• Acid pKa: 7.1906595
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.0053807
• LogD (pH = 7.4): -1.4119005
• Log P: -0.99665326
• Molar Refractivity: 24.046 cm^3
• Polarizability: 9.46607 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Colourless solid; Off-White Solid
• Melting Point: 94-99°C; 94-99°C; 95°C; 95-98 °C; 95-98 °C(lit.); 96-98°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C), Desiccate
• Storage Warning: Hygroscopic; Irritant/Hygroscopic/Moisture Sensitive/Store under Argon
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (T); 98%; 98+%
• Grade: purum
• Empirical Formula (Hill Notation): C4H5NO3

DETAILS

MP Biomedicals - 05204265

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102018

Crystalline
A reagent used for the synthesis of water-soluble active esters and as an additive to suppress enantiomerization during carbodiimide condensations ^[1, 2].

Sigma Aldrich - 130672

Frequently Asked Questions
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Application
Additive used in the carbodiimide method for improved amidations1 and peptide couplings.2
Used to activate a carboxyl group for amide bond formation.
Packaging
1 kg in poly bottle
5 g in glass bottle
25, 100, 250 g in poly bottle
5 kg in poly drum

Sigma Aldrich - 56480

General description
may contain 1-3% succinic acid and/or succinic anhydride

Toronto Research Chemicals - H953585

Additive used in the carbodiimide method for improved amidations and peptide couplings.

REFERENCES

• G. W. Anderson, et al. J. Am. Chem. Soc., 1964, 86, 1839.
• F. Weygand, et al. Z. Naturforsch., 1966, 21, 426.
• Reagent for the preparation of active N-hydroxysuccinimide esters for peptide coupling with minimum racemization: J. Am. Chem. Soc., 86, 1839 (1964), or as an additive in the DCC method (see N,N'-Dicyclohexylcarbodiimide, A10973) to suppress racemization: J. Am. Chem. Soc., 89, 7151 (1967). For peptide reagents, see Appendix 6.
• For a study of the aminolysis of N-hydroxysuccinimide esters, see: J. Org. Chem., 53, 3583 (1988).