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557471

Sigma-Aldrich

4-Nitrothioanisole

96%

Synonym(s):

Methyl-4-nitrophenyl sulfide

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About This Item

Linear Formula:
O2NC6H4SCH3
CAS Number:
701-57-5
Molecular Weight:
169.20
MDL number:
MFCD00010868
UNSPSC Code:
12352100
PubChem Substance ID:
24879673
NACRES:
NA.22

assay

96%

form

solid

mp

66-69 °C (lit.)
68-72 °C (lit.)

SMILES string

CSc1ccc(cc1)[N+]([O-])=O

InChI

1S/C7H7NO2S/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3

InChI key

NEZGPRYOJVPJKL-UHFFFAOYSA-N

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General description

4-Nitrothioanisole in acetone-d6 solution exhibits twofold barrier to rotation about the Csp2-S bond as 16.1±1.5kJ/mol. 4-Nitrothioanisole undergoes hydrogenation in the presence of sulfided Pd/C catalysts.

Application

4-Nitrothioanisole may be used to synthesize 4-nitrothioanisole sulfoxide and methyl 4-nitrophenyl sulfoxide.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Horseradish peroxidase-catalyzed two-electron oxidations. Oxidation of iodide, thioanisoles, and phenols at distinct sites.
Harris RZ, et al.
The Journal of Biological Chemistry, 268(3), 1637-1645 (1993)
Photoelectrochemical reduction of meta-halonitrobenzenes and related species.
Robert AW and George WJ.
J. Chem. Soc. Perkin Trans. II, 8, 1673-1677 (1995)
Catalytic hydrogenation of sulfur-containing nitrobenzene over Pd/C catalysts: In situ sulfidation of Pd/C for the preparation of Pd x S y catalysts.
Zhang Q, et al.
Applied Catalysis A: General, 497, 17-21 (2015)
The proximate coupling constant, 5 J (H, CH3), and the torsional mobility of the thiomethyl group in some thioanisole derivatives.
Schaefer T, et al.
Canadian Journal of Chemistry, 69(4), 620-624 (1991)

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