(1,1-dioxo-1λ6-benzothiophen-2-yl)methyl chloroformate

• ChemBase ID: 294993
• Molecular Formular: C10H7ClO4S
• Molecular Mass: 258.67818
• Monoisotopic Mass: 257.97535738
• SMILES: c1ccc2c(c1)C=C(S2(=O)=O)COC(=O)Cl
• Canonical SMILES: ClC(=O)OCC1=Cc2c(S1(=O)=O)cccc2
• InChI: InChI=1S/C10H7ClO4S/c11-10(12)15-6-8-5-7-3-1-2-4-9(7)16(8,13)14/h1-5H,6H2
• InChIKey: ZYXGPSYADVTJGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1,1-dioxo-1λ^6-benzothiophen-2-yl)methyl chloroformate
• IUPAC Traditional name: (1,1-dioxo-1λ^6-benzothiophen-2-yl)methyl chloroformate
• Synonyms: Benzo[b]thiophenesulfone-2-methoxycarbonyl chloride; Bsmoc-Cl; 1-Dioxobenzo[b]thiophen-2-ylmethyl chloroformate; 1,1-二氧-苯并噻吩-2-甲基 氯甲酸酯

Database IDs

• CAS Number: 135204-19-2
• EC Number: 000-000-0
• MDL Number: MFCD01090984
• Beilstein Number: 8258946
• PubChem SID: 180680524
• PubChem CID: 4565178

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.877971
• LogD (pH = 7.4): 1.877971
• Log P: 1.877971
• Molar Refractivity: 60.4426 cm^3
• Polarizability: 23.687086 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 76-77°C

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: UN3261
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

Product Information

• Purity: tech. 90%

REFERENCES

• Reagent introduced by Carpino for protection of amino acids as their benzothiophenesulfone-2-methoxycarbonyl (Bsmoc) derivatives, which represent a significant improvement in solid-phase peptide synthesis over the corresponding Fmoc derivatives. They are more readily cleaved by base, particularly tris(2-aminoethyl)amine: J. Am. Chem. Soc., 119, 9915 (1997); J. Org. Chem., 64, 4324 (1999).