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Merck
CN

662534

4-Mercaptobenzoic acid

technical grade, 90%

Synonym(s):

4-Carboxybenzenethiol, 4-Carboxythiophenol, 4-Mercaptobenzoic acid, p-Carboxybenzenethiol, p-Mercaptobenzoic acid

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About This Item

Linear Formula:
HSC6H4CO2H
CAS Number:
1074-36-8
Molecular Weight:
154.19
MDL number:
MFCD00016617
UNSPSC Code:
12352100
PubChem Substance ID:
24884591
NACRES:
NA.22

Key Documents

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grade

technical grade

Assay

90%

form

solid

mp

215-224 °C (lit.)

functional group

carboxylic acid

SMILES string

OC(=O)c1ccc(S)cc1

InChI

1S/C7H6O2S/c8-7(9)5-1-3-6(10)4-2-5/h1-4,10H,(H,8,9)

InChI key

LMJXSOYPAOSIPZ-UHFFFAOYSA-N

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General description

4-Mercaptobenzoic acid (4-MBA), also known as 4-Carboxythiophenol or p-Mercaptobenzoic acid, is an aromatic compound used in organic synthesis. 4-MBA promotes the formation of disulfide bonds through its reactive thiol (-SH) group. The sulfur atom in the thiol group is highly nucleophilic, allowing it to attack electrophiles.  facilitates the formation of diverse thiol-containing compounds.  Additionally, 4-MBA serves as a ligand to form coordination complexes and is utilized for surface functionalization, particularly in creating self-assembled monolayers (SAMs) on metal surfaces.

Application

  • SERS substrate for food adulteration detection: 4-Mercaptobenzoic acid was employed in the layer-by-layer biopolymer assembly for the in situ fabrication of AuNP plasmonic paper, serving as a SERS substrate useful in detecting food adulteration (Viriyakitpattana et al., 2024).
  • Development of magneto-plasmonic nanoparticles: Research highlighted the use of 4-Mercaptobenzoic acid in the multiwavelength SERS of magneto-plasmonic nanoparticles, obtained through combined laser ablation and solvothermal methods, showing versatility in nanoparticle synthesis (Talaikis et al., 2023).

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD8518V
MKCQ5928
MKCH7751
MKCD5992
MKCB0454V

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Chitosan-4-mercaptobenzoic acid: synthesis and characterization of a novel thiolated chitosan
Millotti et al.
Journal of Materials Chemistry, 20, 2432-2440 (2010)
Electrochemical and infrared spectroscopy studies of 4-mercaptobenzoic acid SAMs on gold surfaces
Rosendahl et al.
Electrochimica Acta, 53, 6759-6767 (2008)
Coordination chemistry of 3-and 4-mercaptobenzoate ligands: versatile hydrogen-bonding isomers of the thiosalicylate (2-mercaptobenzoate) ligand
Tiekink et al.
Coordination Chemistry Reviews, 341, 19-52 (2017)
A theoretical study of 4-Mercaptobenzoic acid assembled on Ag for surface-enhanced raman scattering applications
Mhlanga et al.
Materials Today Communications, 26, 101698-101698 (2021)
Pablo D Jadzinsky et al.
Science (New York, N.Y.), 318(5849), 430-433 (2007-10-20)
Structural information on nanometer-sized gold particles has been limited, due in part to the problem of preparing homogeneous material. Here we report the crystallization and x-ray structure determination of a p-mercaptobenzoic acid (p-MBA)-protected gold nanoparticle, which comprises 102 gold atoms
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