Difluoromethylthioacetic acid
[CAS# 83494-32-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: Difluoromethylthioacetic acid
• Molecular Formula: C₃H₄F₂O₂S
• Molecular Weight: 142.13
• CAS Registry Number: 83494-32-0
• EC Number: 854-718-1
• SMILES: C(C(=O)O)SC(F)F

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.440, Calc.^*
• Boiling Point: 218.8±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 86.1±25.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Hazard Statements: H302-H315-H318-H410
• Precautionary Statements: P280-P301+P312+P330-P305+P351+P338+P310

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

Difluoromethylthioacetic acid was first synthesized in the late 20th century as part of research into fluorinated organic compounds. Its unique structure features a difluoromethyl group (-CF₂H) attached to a sulfur atom, which in turn is attached to an acetic acid backbone. This was achieved by incorporating fluorine atoms into organosulfur compounds to explore new reactive intermediates for chemical synthesis.

Difluoromethylthioacetic acid can be synthesized by the reaction of difluoromethylthiol with bromoacetic acid or by direct fluorination techniques. The reaction is carried out under controlled conditions, using a suitable base and solvent. Difluoromethylthioacetic acid consists of a -CF₂H group bound to a sulfur atom, which is attached to an acetic acid unit (-COOH). It is a colorless liquid that is soluble in organic solvents; it has limited solubility in water

Difluoromethylthioacetic acid is a valuable intermediate in the synthesis of various drugs. The incorporation of its fluorine and sulfur atoms enhances the pharmacokinetic properties of drugs, improving their stability, bioavailability, and efficacy. Specific applications include use in the development of antiviral drugs, where the difluoromethyl group helps inhibit viral enzymes. As a precursor for the synthesis of compounds that modulate inflammatory pathways, it can be used to treat diseases such as arthritis and asthma. As a component of drugs that affect metabolic processes, it helps treat metabolic disorders.

In agrochemical applications, difluoromethylthioacetic acid is used to synthesize herbicides and fungicides. The presence of the difluoromethylthio group enhances the activity and selectivity of these compounds, making them more effective against pests while minimizing their impact on the environment. It is used to make selective herbicides that control weed growth without damaging crops. It is indispensable in the development of fungicides that protect plants from fungal infections and improve crop yield and quality.

As a versatile building block, difluoromethylthioacetic acid is frequently used in chemical research to explore new fluorinated compounds. Its reactivity with a variety of nucleophiles and electrophiles makes it valuable in the synthesis of complex molecules to study reaction mechanisms and develop new synthetic methods.

Although difluoromethylthioacetic acid is a valuable chemical, it needs to be handled with care. It should be stored in a cool, well-ventilated area away from sources of fire and strong acids or bases. Protective equipment such as gloves and goggles are essential to prevent skin and eye contact. Responsible disposal of difluoromethylthioacetic acid and its derivatives is essential to avoid environmental contamination. Compliance with environmental regulations ensures that their use does not cause pollution or ecological damage.