1-{[(2-methanesulfonylethoxy)carbonyl]oxy}pyrrolidine-2,5-dione

• ChemBase ID: 137812
• Molecular Formular: C8H11NO7S
• Molecular Mass: 265.24044
• Monoisotopic Mass: 265.0256227
• SMILES: CS(=O)(=O)CCOC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCCS(=O)(=O)C
• InChI: InChI=1S/C8H11NO7S/c1-17(13,14)5-4-15-8(12)16-9-6(10)2-3-7(9)11/h2-5H2,1H3
• InChIKey: KSMLVLJMKBLJJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(2-methanesulfonylethoxy)carbonyl]oxy}pyrrolidine-2,5-dione
• IUPAC Traditional name: 1-{[(2-methanesulfonylethoxy)carbonyl]oxy}pyrrolidine-2,5-dione
• Synonyms: MSC-ONSu; N-[2-(Methylsulfonyl)ethoxycarbonyloxy]succinimide; 2-(Methanesulfonyl)ethyl succinimidyl carbonate; 2-(Methylsulfonyl)ethyl N-succinimidyl carbonate; N-[2-(甲磺酰基)乙氧基羰酰氧基]琥珀酰亚胺; 2-(甲磺酰)乙基琥珀酰亚胺基碳酸酯; N-[2-(甲磺酰)乙氧羰基氧基]琥珀酰亚胺; 2-(甲磺酰)乙基 N-琥珀酰亚胺基碳酸酯

Database IDs

• CAS Number: 57903-15-8
• MDL Number: MFCD00043142
• Beilstein Number: 6584148
• PubChem SID: 162232073; 24862860; 24885897
• PubChem CID: 388550

CALCULATED PROPERTIES

• Acid pKa: 17.634207
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -1.5547767
• LogD (pH = 7.4): -1.5547767
• Log P: -1.5547767
• Molar Refractivity: 52.8885 cm^3
• Polarizability: 22.060804 Å^3
• Polar Surface Area: 107.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 112-114 °C (dec.); 115-118 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (N); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C8H11NO7S

DETAILS

Sigma Aldrich - 69228

Other Notes
Reagent for introducing the 2-(methylsulfonyl)ethoxycarbonyl, MSC, amino protecting group.; The MSC group is stable to acid and to hydrogenolysis, but cleaved by base1,2; Used for the protection of insulin as (MSC)2-insulin3,4