3-bromo-3-methyl-2-[(2-nitrophenyl)sulfanyl]-3H-indole

• ChemBase ID: 103060
• Molecular Formular: C15H11BrN2O2S
• Molecular Mass: 363.22904
• Monoisotopic Mass: 361.9724606
• SMILES: CC1(Br)C(=Nc2c1cccc2)Sc1c(cccc1)[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)c1ccccc1SC1=Nc2c(C1(C)Br)cccc2
• InChI: InChI=1S/C15H11BrN2O2S/c1-15(16)10-6-2-3-7-11(10)17-14(15)21-13-9-5-4-8-12(13)18(19)20/h2-9H,1H3
• InChIKey: BXTVQNYQYUTQAZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-bromo-3-methyl-2-[(2-nitrophenyl)sulfanyl]-3H-indole
• IUPAC Traditional name: 3-bromo-3-methyl-2-[(2-nitrophenyl)sulfanyl]indole
• Synonyms: 2-(2-Nitrophenylsulfenyl)-3-methyl-3-bromoindolenine; BNPS-skatol; 3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole; 2-(2-nitrophenylsulfenyl)-3-methyl-3'-bromoindolenine; 3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole; 3-Bromo-3-methyl-2-(2-nitrophenylmercapto)-3H-indole; BNPS-SKATOLE

Database IDs

• CAS Number: 27933-36-4
• EC Number: 248-737-9
• MDL Number: MFCD00037978
• Beilstein Number: 1491457
• PubChem SID: 162090263; 24891797
• PubChem CID: 94388

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.2755585
• LogD (pH = 7.4): 5.2755923
• Log P: 5.275593
• Molar Refractivity: 90.4539 cm^3
• Polarizability: 33.04124 Å^3
• Polar Surface Area: 58.18 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• 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: ≥85%; ≥96.0% (TLC)
• Empirical Formula (Hill Notation): C15H11BrN2O2S

DETAILS

MP Biomedicals - 02150479

Used to modify tryptophan in proteins when the sulfhydryl groups are protected.

Sigma Aldrich - B4651

Application
Peptide cleavage reagent specific for the carboxyl side of tryptophan residues.

Sigma Aldrich - 17625

Other Notes
For the specific cleavage of proteins at the carboxylic side of tryptophanyl residues1,2

REFERENCES

• Hunziker, P.E., et al., Biochem. J. , 187 : 515, (1980).