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N27209

Sigma-Aldrich

4-Nitrothiophenol

technical grade, 80%

Synonym(s):

p-Nitrophenyl mercaptan, pNTP, 4-Nitrobenzenethiol

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About This Item

Linear Formula:
O2NC6H4SH
CAS Number:
1849-36-1
Molecular Weight:
155.17
Beilstein:
606924
EC Number:
217-436-4
MDL number:
MFCD00007343
UNSPSC Code:
12352100
PubChem Substance ID:
24897587
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

80%

form

solid

mp

72-77 °C (lit.)

storage temp.

2-8°C

SMILES string

[O-][N+](=O)c1ccc(S)cc1

InChI

1S/C6H5NO2S/c8-7(9)5-1-3-6(10)4-2-5/h1-4,10H

InChI key

AXBVSRMHOPMXBA-UHFFFAOYSA-N

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Application

4-Nitrothiophenol has been used in the synthesis of dual emission fluorescent probe for the differential sensing of of glutathione (GSH) and cysteine/homocysteine (Cys/Hcy). pNTP can also be used to synthesize diaryl thioethers via copper-catalyzed C-S coupling reaction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ligand-free copper-catalyzed C? S coupling of aryl iodides and thiols.
Sperotto E, et al.
The Journal of Organic Chemistry, 73(14), 5625-5628 (2008)
Itai Chipinda et al.
Chemical research in toxicology, 23(5), 918-925 (2010-04-21)
The need for alternatives to animal-based skin sensitization testing has spurred research on the use of in vitro, in silico, and in chemico methods. Glutathione and other select peptides have been used to determine the reactivity of electrophilic allergens to
Y Segall et al.
Mutation research, 158(1-2), 61-68 (1985-10-01)
The mutagenicity of halopropenals for Salmonella typhimurium strain TA100 is as follows (revertants/nmole): 2-halopropenals [H2C = C(X)CHO], F = less than 0.6, Cl = 135, Br = 1140 and I = less than 2.4; 3-substituted-2-halopropenals [CH3CH = C(X)CHO], Cl =
A dual emission fluorescent probe enables simultaneous detection of glutathione and cysteine/homocysteine.
Yang X F, et al.
Chemical Science, 5(6), 2177-2183 (2014)
Ze-Yuan Dong et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(13), 3575-3579 (2006-02-24)
To elucidate the relationships between molecular recognition and catalytic ability, we chose three assay systems using three different thiol substrates, glutathione (GSH), 3-carboxyl-4-nitrobenzenethiol (CNBSH), and 4-nitrobenzenethiol (NBSH), to investigate the glutathione peroxidase (GPx) activities of 2,2'-ditellurobis(2-deoxy-beta-cyclodextrin) (2-TeCD) in the presence
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