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365246

Sigma-Aldrich

2-Nitrophenyl selenocyanate

97.5%

Synonym(s):

1-Nitro-2-selenocyanatobenzene, o-Nitrophenyl selenocyanate, o-Nitrophenyl selenocyanide, o-Nitrophenylselenyl cyanide

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About This Item

Linear Formula:
O2NC6H4SeCN
CAS Number:
51694-22-5
Molecular Weight:
227.08
Beilstein:
1309777
EC Number:
257-350-4
MDL number:
MFCD00043146
UNSPSC Code:
12352100
PubChem Substance ID:
24862498
NACRES:
NA.22

Assay

97.5%

mp

140-142 °C (lit.)

functional group

nitro

SMILES string

[O-][N+](=O)c1ccccc1[Se]C#N

InChI

1S/C7H4N2O2Se/c8-5-12-7-4-2-1-3-6(7)9(10)11/h1-4H

InChI key

LHBLJWULWKQRON-UHFFFAOYSA-N

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General description

2-Nitrophenyl selenocyanate is a chromophoric selenium compound.

Application

2-Nitrophenyl selenocyanate (o-nitrophenyl selenocyanate) may be used:
  • to study the mechanism of its reaction with the zinc/thiolate clusters of metallothionein
  • in the preparation of 2,3-seco-5 α-cholestane-2,3-diol
  • in the preparation of 4α-methyl-2,3-seco-5 α-cholestane-2,3-diol
  • in the preparation of 2-nitrophenylselenyl derivative
  • in the synthesis of 3α-[(2-Nitrophenyl)seleno]androsta-1,5-dien-17β-ol

Signal Word

Danger

Hazard Statements

H301 + H331,H373,H410

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3840
BCCH2078
BCCC1075
BCBZ4212
BCBW3136

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M Arnó et al.
Steroids, 43(3), 305-314 (1984-03-01)
The reaction of 2,3-seco-5 alpha-cholestane-2,3-diol and 4 alpha-methyl-2,3-seco-5 alpha-cholestane-2,3-diol with o-nitrophenyl selenocyanate was studied. The diols were synthesized from cholesterol.
Shaoman Zhou et al.
Journal of medicinal chemistry, 49(20), 6120-6128 (2006-09-29)
All stereoisomers of adenine and guanine methylene-3-fluoromethylenecyclopropane analogues of nucleosides 9a, 9b, 10a, 10b, 11a, 11b, 12a, and 12b were synthesized and their antiviral activities were evaluated. A highly convergent approach permitted the synthesis of all these analogues using a
Synthesis and radical oxidation of steroidal 1-oxo-5α-alcohols.
Khripach VA, et al.
ARKIVOC (Gainesville, FL, United States), 9, 20-28 (2008)
Wenyi Zheng et al.
Analytical chemistry, 89(14), 7586-7592 (2017-06-24)
p-Xyleneselenocyanate (p-XSC) is one of the most investigated selenium compounds in cancer-prevention and -therapy. Despite the potent anticancer property, there is still no proper method to perform the quantitative analysis of p-XSC in plasma. In this investigation, we aimed at
Y Chen et al.
Antioxidants & redox signaling, 3(4), 651-656 (2001-09-14)
Zinc/thiolate (cysteine) coordination occurs in a very large number of proteins. These coordination sites are thermodynamically quite stable. Yet the redox chemistry of thiolate ligands confers extraordinary reactivities on these sites. The significance of such ligand-centered reactions is that they

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