5-(Ethylthio)-1H-tetrazole CAS No. 89797-68-2

Product Description

5-(Ethylthio)-1H-tetrazole is a derivative of 1H-tetrazole with an ethylthio group (–S–CH₂CH₃) attached to the 5-position of the tetrazole ring. The tetrazole ring is a five-membered heterocycle containing four nitrogen atoms and one carbon atom. This compound is typically a white to off-white solid and is more soluble in polar organic solvents like DMSO and methanol than in water due to the hydrophobic ethyl group. It is commonly used as an intermediate in organic synthesis, particularly in medicinal chemistry, where tetrazole derivatives serve as bioisosteres for carboxylic acids. The ethylthio group can also act as a leaving group or be further modified in chemical reactions. However, tetrazoles can be explosive under certain conditions, especially when dry, so they should be handled with care, avoiding strong oxidizers and high temperatures.

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Product Use & Characteristics

Molecular Formula: C₃H₆N₄S
Molecular Weight: 130.169 g/mol
IUPAC Name: 5-ethylsulfanyl-2H-tetrazole

Structure:

• The compound is a derivative of 1H-tetrazole with an ethylthio group (–S–CH₂CH₃) attached to the 5-position of the tetrazole ring.

• The tetrazole ring is a five-membered heterocycle containing four nitrogen atoms and one carbon atom.

Physical Properties:

• Appearance: Likely a white to off-white solid.

• Melting Point: Varies slightly depending on the source, but generally in the range of 72-90 °C.

• Boiling Point: Around 81-82 °C.

• Solubility: Soluble in water (clear, colorless solution) and acetonitrile; may be slightly soluble in water and easily soluble in common organic solvents such as ethanol, DMF, DMSO, etc.

• Acidity: More acidic than 1H-tetrazole itself, with the tetrazole ring having strong acidity (especially hydrogen at position 1, pKa ≈ 4.5–5).

• Stability: Stable under normal conditions but can decompose rapidly and may explode if heated above 155 °C.

Chemical Properties:

• The tetrazole ring has strong acidity and can form salts with metals.

• The ethylthio group has a certain electron-donating effect, which may affect the reactivity of the tetrazole ring.

• It can participate in a variety of nucleophilic or electrophilic substitution reactions and is suitable for functional modification in medicinal chemistry and materials science.

Synthesis Methods

• One common method for preparing 5-(Ethylthio)-1H-tetrazole involves the [2+3] cycloaddition of alkyl thiocyanate and sodium azide under phase transfer catalytic conditions. The solvent ratio (water to toluene) and reaction temperature are crucial for achieving good yields.

• It has also been synthesized using DMF as a solvent, though with lower yields.

• Other methods include reacting the corresponding nitrile compound with azide in the presence of thiol (or thioether) for [3+2] cycloaddition reaction, or preparing it by multi-step reaction of thioacetamide and hydrazine compounds.

Uses

• Organic Synthesis: Used as an intermediate in organic synthesis, particularly in medicinal chemistry.

• Pharmaceuticals: Tetrazole derivatives are important in pharmaceuticals, for example, as bioisosteres for carboxylic acids. 5-(Ethylthio)-1H-tetrazole can be used as an intermediate to synthesize biologically active compounds, such as antihypertensive drugs (e.g., angiotensin II receptor antagonists).

• Nucleic Acid Synthesis: It is a powerful activator in DNA and RNA synthesis, particularly in oligonucleotide synthesis, where it activates nucleoside phosphoramidites, facilitating their condensation with a nucleoside to form dinucleoside phosphates.

• Agricultural Chemistry: Used in the formulation of agrochemicals to enhance the efficacy of pesticides and herbicides.

• Material Science: Investigated for its potential in developing new materials with improved thermal stability and mechanical strength.

• Analytical Chemistry: Used as a reagent in analytical methods for the detection and quantification of other chemical species.

• Biochemical Assays: Utilized in research to understand enzyme activity and metabolic pathways.

• Ligands and Metal Complexes: Tetrazole can be used as a multidentate ligand to form stable complexes with metal ions, which are used in catalysis, magnetic materials, and other fields.

• High-Energy Materials: Some tetrazole derivatives have high nitrogen content and can be used as components of propellants or explosives.

Safety Information

• Hazard Statements:

  • H225: Highly flammable liquid and vapor

  • H302+H312+H332: Harmful if swallowed, in contact with skin, or if inhaled

  • H315: Causes skin irritation

  • H318: Causes serious eye damage

  • H335: May cause respiratory irritation

• Handling and Storage:

  • Appropriate personal protective equipment (PPE) such as a dust mask (N95), eyeshields, and gloves should be used when handling this compound.

  • It should be stored in a cool, dark place, typically at 2-8°C.

• General Safety: Tetrazoles can be explosive under certain conditions, especially when dry. They should be handled with care, avoiding strong oxidizers and high temperatures.

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Sigma Chemical Group is a major chemical enterprise headquartered in Hangzhou, Zhejiang Province, with a diversified portfolio of subsidiaries including Henan Sigma Biotechnology Co., Ltd, QIngdao Sigma Chemical Co.,Ltd, Nanchang Sigma Chemical Co., Ltd., and Jinan Sigma Chemical Co., Ltd. Established on January 16, 2017, Qingdao Sigma Chemical Co., Ltd. operates as a micro-sized chemical product wholesaler with a registered capital of RMB 100,000. Led by legal representative Yang Yuwen and based at 2-1-2301, Jiahe Xinxing, No. 130 Shandong Road, Shibei District, Qingdao, the company’s operations span chemicals, machinery equipment, and import-export services. Henan Sigma Biotechnology Co., Ltd, located in Dongmafang, Muye District, Xinxiang City, Henan Province, specializes in the sales of pesticides, pharmaceuticals, veterinary drugs, and mixed feed additive series, including products like adenine, florfenicol injection, carbasalate calcium soluble powder, and cefotaxime sodium chloride injection. Guided by a win-win and innovative business philosophy, the company employs a modern management approach and customer-centric service, upholding integrity, diligence, and a commitment to quality, thereby earning customer trust through diverse product offerings and competitive pricing. Nanchang Sigma Chemical Co., Ltd., situated in Nanchang, Jiangxi Province, is dedicated to producing high-purity plant extracts, emphasizing eco-friendly, non-toxic chemical raw materials that generate no environmental pollutants. Jinan Sigma Chemical Co., Ltd., located in Jinan, the capital of Shandong Province known as the "City of Springs," focuses on manufacturing active pharmaceutical ingredients (APIs) and pharmaceutical intermediates. The company maintains long-term industry-academia-research collaborations with Shandong University and Qilu University of Technology, continuously enhancing R&D investments to drive innovation and growth.