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303232

3-Nitro-2-pyridinesulfenyl chloride

Name: 3-Nitro-2-pyridinesulfenyl chloride
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

24858307

UNSPSC Code:

12352100

MDL number:

MFCD00274609

Assay:

95%

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Properties

Quality Level

100

assay

95%

mp

205 °C (dec.) (lit.)

solubility

dichloromethane: soluble(lit.)

functional group

nitro

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

Description

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

GHS05

signalword

Danger

hcodes

H314

pcodes

P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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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Use of the 3-nitro-2-pyridine sulfenyl protecting group to introduce N epsilon-branching at lysine during solid-phase peptide synthesis. I. Application to the synthesis of a peptide template containing two addressable sites.

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

Compatibility of the S-(3-nitro-2-pyridinesulfenyl) protecting group with DCC/HOBt coupling chemistry.

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

Thiolysis of the 3-nitro-2-pyridinesulfenyl (Npys) protecting group. An approach towards a general deprotection scheme in peptide synthesis.

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

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Global Trade Item Number

SKU	GTIN
303232-1G	04061825970295