1,4-Benzenedimethanethiol
[CAS# 105-09-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiol/thiophenol
• Name: 1,4-Benzenedimethanethiol
• Molecular Formula: C₈H₁₀S₂
• Molecular Weight: 170.29
• CAS Registry Number: 105-09-9
• EC Number: 203-269-4
• SMILES: C1=CC(=CC=C1CS)CS

Properties

• Melting point: 45-46 °C
• Boiling point: 156 °C
• Flash point: 113 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1,4-Benzenedimethanethiol, commonly known as 1,4-bis(methylthio)benzene, is an organosulfur compound with the molecular formula C₆H₄(CH₂SH)₂. It consists of a benzene ring with two methylthiol groups attached at the 1 and 4 positions. The compound is a pale yellow crystalline solid with a characteristic thiol (sulfur) odor and is soluble in organic solvents such as ethanol, chloroform, and ether. The presence of the thiol group makes it reactive towards various chemical transformations, especially in forming strong bonds with metals and in thiol-disulfide exchange reactions. 1,4-Benzenedimethanethiol was synthesized during the development of organosulfur chemistry in the early 20th century.

1,4-Benzenedimethanethiol is used as a building block in organic synthesis to introduce thiol groups into molecules. The thiol group can undergo a variety of reactions, including alkylation, oxidation, and metal coordination. 1,4-Benzenedimethanethiol acts as a ligand in catalytic processes. It forms stable complexes with transition metals and is used in a variety of catalytic transformations, including those in the field of green chemistry.

1,4-Benzenedimethanethiol forms self-assembled monolayers on gold surfaces. These monolayers are essential for the development of nanomaterials and devices, including sensors and molecular electronics. The thiol groups bind tightly to gold, forming ordered layers that can modify the surface properties of the substrate. 1,4-Benzenedimethanethiol is added to polymer matrices to enhance durability and chemical resistance. Its sulfur content can increase the mechanical strength and elasticity of polymers for specialized applications.

1,4-Benzenedimethanethiol is used in environmental chemistry to remove heavy metals from contaminated water and soil. The thiol groups of 1,4-Benzenedimethanethiol have a high affinity for heavy metals, which can be effectively chelated and removed from the environment. 1,4-Benzenedimethanethiol is used in waste treatment processes to neutralize and precipitate heavy metals and prevent their release into the environment.

1,4-Benzenedimethanethiol is used in analytical techniques to detect and quantify metal ions. The compound can form colored complexes with metals to analyze metal concentrations in various samples by spectroscopic detection. 1,4-Benzenedimethanethiol is a key component in the development of chemical sensors, especially for the detection of thiol-reactive substances.

1,4-Benzenedimethanethiol is studied as a precursor for drug design and development. The introduction of thiol groups can enhance the biological activity of drugs by promoting binding interactions with biological targets such as enzymes and receptors. 1,4-Benzenedimethanethiol liquids are used to explore prodrug strategies to improve the delivery and activation of therapeutic agents. The thiol group is used to release active drugs under specific conditions, thereby enhancing their efficacy and reducing side effects.

References

2010. Synthesis by Substitution of Dihaloalkanes. Science of Synthesis, SD-045-01382.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-045-01382

2010. Self-Assembly of 1,4-Benzenedimethanethiol Self-Assembled Monolayers on Gold. Langmuir : the ACS journal of surfaces and colloids, 26(5), 20199099.
DOI: 10.1021/la904317b

2011. UPS, XPS, and NEXAFS Study of Self-Assembly of Standing 1,4-Benzenedimethanethiol SAMs on Gold. Langmuir : the ACS journal of surfaces and colloids, 27(6), 21405080.
DOI: 10.1021/la105063u