3-Bromo-3-methyl-2-((2-nitrophenyl)thio)-3H-indole
Basic information
- CAS
27933-36-4- Standard SMILES
CC1(Br)C(Sc2ccccc2[N+](=O)[O-])=Nc2ccccc21- InChIKey
BXTVQNYQYUTQAZ-UHFFFAOYSA-N- Molecular formula
- C15H11BrN2O2S
- Average molar mass
- 363.2 g/mol
- Monoisotopic mass
- 361.97246
Overview
BNPS-skatole is a bromoindole that is 3H-indole in which the hydrogen at position 2 has been replaced by an (o-nitrophenyl)sulfanyl group and in which the hydrogens at position 3 have been replaced by a bromine and a methyl group. It is used particularly for the selective cleavage of tryptophanyl peptide bonds (cleavage occurs at peptide bonds after amino acids with available Cgamma=Cdelta double bonds such as tryptophan, tyrosine, and histidine). It has a role as a reagent. It is an aryl sulfide, a C-nitro compound and a bromoindole.
Names & identifiers
- Preferred name
- 3-Bromo-3-methyl-2-((2-nitrophenyl)thio)-3H-indole
- IUPAC
- 3-bromo-3-methyl-2-(2-nitrophenyl)sulfanylindole
- English name
- (8S-(8alpha,9beta,10alpha,13alpha,14beta))-Hexadecahydro-10,13-dimethy l-1H-cyclopenta(a)phenanthrene
- Molecular weight
- 0
Names & synonyms
Bnps-skatole27933-36-43-Bromo-3-methyl-2-((2-nitrophenyl)thio)-3H-indole2-(2-Nitrophenylsulfenyl)-3-methyl-3-bromoindolenineCHEBI:859683-Bromo-3-methyl-2-[(2-nitrophenyl)thio]-3H-indole3H-Indole, 3-bromo-3-methyl-2-((2-nitrophenyl)thio)-3H-Indole, 3-bromo-3-methyl-2-[(2-nitrophenyl)thio]-RefChem:120831248-737-93-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole3-bromo-3-methyl-2-(2-nitrophenyl)sulfanylindole
Show more names
(8S-(8alpha,9beta,10alpha,13alpha,14beta))-Hexadecahydro-10,13-dimethy l-1H-cyclopenta(a)phenanthrene
MLS0033894553-bromo-3-methyl-2-[(2-nitrophenyl)sulfanyl]-3H-indole2-(2'-Nitrophenylsulphanyl)-3-methyl-3-bromoindolenineEINECS 248-737-9NSC240875NSC 24087528805-72-3SCHEMBL168417
Database identifiers
- CAS
27933-36-4、28805-72-3- PubChem CID
- 94388
- DTXSID
DTXSID00951447- ChEMBL
CHEMBL2144631- ChEBI
CHEBI:85968- EC Number
- 248-737-9
- Nikkaji
- J250.616E
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 83.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 453
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Hazard information
Hazard Classes and Categories
Skin Irrit. 2 (100%)
Aquatic Chronic 4 (100%)
Chemistry & industry
Additional notes
DefinitionChEBI: BNPS-skatole is a bromoindole that is 3H-indole in which the hydrogen at position 2 has been replaced by an (o-nitrophenyl)sulfanyl group and in which the hydrogens at position 3 have been replaced by a bromine and a methyl group. It is used particularly for the selective cleavage of tryptophanyl peptide bonds (cleavage occurs at peptide bonds after amino acids with available C(gamma)=C(delta) double bonds such as tryptophan, tyrosine, and histidine). It has a role as a reagent. It is an aryl sulfide, a C-nitro compound and a bromoindole.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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