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Sigma-Aldrich

3-Nitro-2-pyridinesulfenyl chloride

95%

Synonym(s):

(3-Nitro-2-pyridyl)sulfenyl chloride, 2-(Chlorosulfanyl)-3-nitropyridine, 3-Nitropyridinyl-2-sulfenyl chloride, [(3-Nitropyridin-2-yl)sulfanyl]chlorane

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About This Item

Empirical Formula (Hill Notation):
C5H3ClN2O2S
CAS Number:
68206-45-1
Molecular Weight:
190.61
MDL number:
MFCD00274609
UNSPSC Code:
12352100
PubChem Substance ID:
24858307
NACRES:
NA.22

Assay

95%

mp

205 °C (dec.) (lit.)

solubility

dichloromethane: soluble(lit.)

storage temp.

2-8°C

SMILES string

[O-][N+](=O)c1cccnc1SCl

InChI

1S/C5H3ClN2O2S/c6-11-5-4(8(9)10)2-1-3-7-5/h1-3H

InChI key

WTKQMHWYSBWUBE-UHFFFAOYSA-N

Related Categories

General description

The 3-nitro-2-pyridinesulphenyl (Npys) moiety is useful as a protecting-activating group for cysteine, particularly in the synthesis of cyclic and unsymmetrical disulfides. The stability of NpysCl was studied in various solvents.

Application

3-Nitro-2-pyridinesulfenyl chloride (NpysCl) was employed as the starting material for the synthesis of N-, O- and S-Npys-protected amino acid.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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O Rosen et al.
International journal of peptide and protein research, 35(6), 545-549 (1990-06-01)
The hydroxylic side-chain functional groups of serine, threonine, hydroxproline and tyrosine, the alpha and epsilon-amino moieties of lysine and the thiol group of cysteine were masked by the 3-nitro-2-pyridinesulfenyl (Npys) protecting group. Deprotection was mildly affected by thiolysis with either
R Matsueda et al.
Peptide research, 5(5), 262-264 (1992-09-01)
Two recent reports on the partial lability of the 3-nitro-2-pyridinesulfenyl (Npys) thiol protecting group towards 1-hydroxy-benzotriazole (HOBt) have prompted a rechecking of the chemical behavior of this group. Using both soluble and polymer-bound forms of Cys(Npys) as test materials, the
S Rajagopalan et al.
International journal of peptide and protein research, 45(2), 173-179 (1995-02-01)
TASPs (template-assembled synthetic peptides) are generated by the covalent attachment of linear peptides to a common peptide backbone, thus generating larger synthetic peptides/proteins with prefolded structure. In this work we present a strategy for the synthesis of a heterotemplate-assembled synthetic
Y Shimohigashi et al.
Journal of chromatography, 597(1-2), 425-428 (1992-04-24)
The thiol groups of leucinthiol, cysteamine and cysteine incorporated into opioid peptides enkephalin and morphiceptin were activated by the 3-nitro-2-pyridinesulphenyl (Npys) group to form mixed disulphides highly reactive to a free thiol. Enkephalin analogues containing Npys-leucinthiol or -cysteine at positions
K C Pugh et al.
International journal of peptide and protein research, 42(2), 159-164 (1993-08-01)
3-Nitro-2-pyridinesulfenyl chloride (NpysCl) is the starting material for the synthesis of N-, O- and S-Npys-protected amino acids. Two efficient, novel synthetic routes to NpysCl are described. The stability of NpysCl was determined in a variety of solvents, with and without
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