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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

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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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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)
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)
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)
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