(1,1-dioxo-1λ?-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate

• ChemBase ID: 134452
• Molecular Formular: C14H11NO7S
• Molecular Mass: 337.30464
• Monoisotopic Mass: 337.0256227
• SMILES: c1ccc2c(c1)C=C(S2(=O)=O)COC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)OCC1=Cc2c(S1(=O)=O)cccc2
• InChI: InChI=1S/C14H11NO7S/c16-12-5-6-13(17)15(12)22-14(18)21-8-10-7-9-3-1-2-4-11(9)23(10,19)20/h1-4,7H,5-6,8H2
• InChIKey: XBVMGLSMCWWRLS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1,1-dioxo-1λ?-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate; (1,1-dioxo-1λ^6-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate
• IUPAC Traditional name: (1,1-dioxo-1λ?-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate; (1,1-dioxo-1λ^6-benzothiophen-2-yl)methyl 2,5-dioxopyrrolidin-1-yl carbonate
• Synonyms: Carbonic acid, (1,1-dioxidobenzo[b]thien-2-yl)methyl 2,5-dioxo-1-pyrrolidinyl ester; N-(Benzo[b]thiophenesulfone-2-methoxycarbonyl)succinimide; 1,1-Dioxobenzo[b]thiophen-2-ylmethyl N-succimidyl carbonate; Bsmoc-OSu; N-(Benzo[b]thiophenesulfone-2-methoxycarbonyloxy)succinimide; 1,1-Dioxobenzo[b]thiophen-2-ylmethyl N-succinimidyl carbonate; (1,1-二氧-苯并噻吩-2-甲基) 丁二酸亚胺基 甲酸酯; (1,1-二氧-苯并噻吩-2-甲基)丁二酸亚胺基甲酸酯; 1,1-二杂苯[B]硫代苯甲基 N-琥珀酸胺碳酸盐

Database IDs

• CAS Number: 197244-91-0
• MDL Number: MFCD03095506
• Beilstein Number: 8274967
• PubChem SID: 24857579; 162228728
• PubChem CID: 3344958

CALCULATED PROPERTIES

• Acid pKa: 17.63414
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.71422684
• LogD (pH = 7.4): 0.71422684
• Log P: 0.71422684
• Molar Refractivity: 77.1379 cm^3
• Polarizability: 30.528145 Å^3
• Polar Surface Area: 107.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~165 °C (dec.); 140°C dec.

Safety Information

• Storage Warning: Moisture Sensitive
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0%; 95%; min 98%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C14H11NO7S

DETAILS

Sigma Aldrich - 29237

Other Notes
New base- and nucleophile-sensitive amino-protecting group in peptide coupling, more base-labile than Fmoc, deprot. by tris(2-aminoethyl)amine (TAEA)1

REFERENCES

• Reagent introduced by Carpino for protection of amino acids as their benzothiophenesulfone-2-methoxycarbonyl (Bsmoc) derivatives (see 1,1-Dioxobenzo[b]thiophen-2-ylmethyl chloroformate, L19559): J. Am. Chem. Soc., 119, 9915 (1997); J. Org. Chem., 64, 4324 (1999).