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303232

Sigma-Aldrich

3-Nitro-2-pyridinesulfenyl chloride

95%

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Synonym(s):
(3-Nitro-2-pyridyl)sulfenyl chloride, 2-(Chlorosulfanyl)-3-nitropyridine, 3-Nitropyridinyl-2-sulfenyl chloride, [(3-Nitropyridin-2-yl)sulfanyl]chlorane
Empirical Formula (Hill Notation):
C5H3ClN2O2S
CAS Number:
Molecular Weight:
190.61
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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3-Nitro-2-pyridinesulfenyl chloride 95%

303232

3-Nitro-2-pyridinesulfenyl chloride

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4-Morpholinecarbonyl chloride 98%

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4-Morpholinecarbonyl chloride

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N-(Trimethylsilyl)acetamide 95%

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N-(Trimethylsilyl)acetamide

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Sodium chloride puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.5%

31434

Sodium chloride

Essential Grade
solubility

dichloromethane: soluble(lit.)

solubility

-

solubility

-

solubility

water: soluble 100 mg/mL, clear, colorless

mp

205 °C (dec.) (lit.)

mp

-

mp

46-49 °C (lit.)

mp

801 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

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

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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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
R G Simmonds et al.
International journal of peptide and protein research, 43(4), 363-366 (1994-04-01)
The 3-nitro-2-pyridinesulphenyl (Npys) moiety is finding increasing utility as a protecting-activating group for cysteine, particularly in the synthesis of cyclic and unsymmetrical disulfides using the Boc strategy. This chemistry has been extended to peptides assembled by the Fmoc strategy. N-Terminal
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, 7(1), 32-35 (1994-01-01)
Thrombin-induced platelet aggregation has been suggested to play an important role in reocclusion following thrombolytic therapy or angioplasty for treatment of myocardial infarction. We previously demonstrated that thrombin-induced platelet aggregation is indirectly mediated by intracellularly activated calpain expressed on the

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