2,5-dioxopyrrolidin-1-yl 3-(acetylsulfanyl)propanoate

• ChemBase ID: 152398
• Molecular Formular: C9H11NO5S
• Molecular Mass: 245.25234
• Monoisotopic Mass: 245.03579346
• SMILES: CC(=O)SCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCSC(=O)C
• InChI: InChI=1S/C9H11NO5S/c1-6(11)16-5-4-9(14)15-10-7(12)2-3-8(10)13/h2-5H2,1H3
• InChIKey: ZRTJVRDXVSDKPX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-(acetylsulfanyl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-(acetylsulfanyl)propanoate
• Synonyms: N-Succinimidyl 3-(acetylthio)propionate; SATP; 3-(Acetylthio)propionic acid N-succinimidyl ester; Ethanethioic Acid S-[3-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-3-oxopropyl] Ester; 3-(Acetylthio)propanoic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; N-Succinimidyl-S-acetylthiopropionate; N-琥珀酰亚胺-3-乙酰硫代丙酸酯

Database IDs

• CAS Number: 84271-78-3
• MDL Number: MFCD00133023
• Beilstein Number: 5562810
• PubChem SID: 162246543; 24846812
• PubChem CID: 4110341

CALCULATED PROPERTIES

• Acid pKa: 17.708979
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.3420187
• LogD (pH = 7.4): -0.3420187
• Log P: -0.3420187
• Molar Refractivity: 55.0955 cm^3
• Polarizability: 22.00298 Å^3
• Polar Surface Area: 80.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Beige Solid
• Melting Point: 48-50°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0%
• Empirical Formula (Hill Notation): C9H11NO5S

DETAILS

Sigma Aldrich - 10859

Other Notes
Reagent for the modification of peptides and proteins: thionylation1
Packaging
50 mg in poly bottle

Toronto Research Chemicals - S690095

Reacts with primary amines to add protected sulfhydryls.

REFERENCES

• Duncan, R.J.S., et al.: Anal. Biochem., 132, 68 (1983)