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422967

Sigma-Aldrich

4-Aminothiophenol

≥97.0%

Synonym(s):

4-Aminobenzenethiol, 4-Aminophenyl mercaptan, 4-Mercaptoaniline

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About This Item

Linear Formula:
H2NC6H4SH
CAS Number:
1193-02-8
Molecular Weight:
125.19
Beilstein:
906904
EC Number:
214-763-4
MDL number:
MFCD00007880
UNSPSC Code:
12352100
PubChem Substance ID:
24866468
NACRES:
NA.22

Quality Level

100

Assay

≥97.0%

bp

140-145 °C/16 mmHg (lit.)

mp

37-42 °C (lit.)

storage temp.

2-8°C

SMILES string

Nc1ccc(S)cc1

InChI

1S/C6H7NS/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2

InChI key

WCDSVWRUXWCYFN-UHFFFAOYSA-N

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General description

4-Aminothiophenol is a bifunctional aromatic thiol used to form self-assembled monolayers for biosensors.

4-Aminothiophenol (p-aminothiophenol, PATP) is an aromatic thiol. The self-assembly of silver and gold nano particles which are interconnected with 4-ATP to form metal-molecule-metal sandwich architecture has been characterized by surface enhanced Raman scattering (SERS) using an off-surface plasmon resonance condition. Chemical transformation of PATP to 4,4-dimercaptoazobenzene (DMAB) has been extensively studied.

Application

4-Aminothiophenol (4-ATP) was employed as bifunctional molecule to functionalize gold nanoparticles (NPs) used in surface-enhanced Raman spectroscopy (SERS) detection of thrombin by protein recognition.

It may be used in the following studies:
  • As a water insoluble ligand in the synthesis of pectin–4-aminothiophenol conjugates.
  • To functionalize gold nanorods (GNR) in the development of GNR nitrite sensor.
  • To form self-assembled monolayers (SAMs) of 4-aminothiophenol in the development of DNA biosensor.
  • As a linker to thiol (SH) functionalize multiwalled carbon nanotubes (MWCNTs).
  • To generate amino terminated self-assembly monolayers(SAMs) on platinum electrode which forms the base for attachment of single-wall carbon nano tubes (SWCTs).

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Attachment of single-wall carbon nanotubes on platinum surfaces by self-assembling techniques.
Rosario-Castro BI, et al.
Reviews on Advanced Materials, 10, 381-386 (2005)
Surface-enhanced Raman scattering of 4-aminothiophenol self-assembled monolayers in sandwich structure with nanoparticle shape dependence: off-surface plasmon resonance condition.
Hu X, et al.
The Journal of Physical Chemistry C, 111(19), 6962-6969 (2007)
4-Aminothiophenol Self-Assembled Monolayer for the Development of a DNA Biosensor Aiming the Detection of Cylindrospermopsin Producing Cyanobacteria.
Valerio E, et al.
Electroanalysis, 20(22), 2467-2474 (2008)
Effect of aqueous and ambient atmospheric environments on plasmon-driven selective reduction reactions.
Ding Q, et al.
Scientific Reports, 5 (2015)
4-aminothiophenol-intercalated montmorillonite: Organic-inorganic hybrid material as an immobilization support for biosensors
Yahya Yasin Y et al.
Sensors and Actuators B, Chemical, 307, 127665-127665 (2020)
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