Periodinane CAS 87413-09-0

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The representative compound of Periodinane,DMP, is an efficient and highly selective oxidizing agent. Its chemical formula is C₁₃H₁₃IO₈, and it appears as colorless to pale yellow crystals. The melting point is 130-133℃. It is easily soluble in organic solvents such as chloroform and acetone. The core structure of this compound is a high-valent iodine (V) compound. Through oxygen atom bridges, it connects two acetoxy groups and a benzene ring, forming a stable five-membered ringed its structure. The most prominent electronic effect of this reagent is its selectivity in the oxidation of alcohols: primary alcohols can be oxidized gently to aldehydes, secondary alcohols to ketones.

The reaction conditions are close to room temperature and do not require strong acids or heavy metal catalysts, avoiding the excessive oxidation or environmental pollution problems caused by traditional oxidants (such as chromates). Its oxidation mechanism relies on the high positive charge of the iodine (V) center, achieving efficient conversion through single electron transfer or cooperative oxygen transfer processes. At the same time, it has excellent compatibility with sensitive functional groups (such as double bonds, acetal groups), and is widely used in the synthesis of drug intermediates and natural products.

Reagent preparation

Step 1

Add 730 ml of 0.73M sulfuric acid to a 2L clean flask, and carefully add 85.2 g of o-iodobenzoic acid [CAS: 88-67-5] while stirring; while maintaining vigorous stirring and keeping the temperature below 55°C, carefully add Add 76 grams of potassium bromate. After the addition is complete, allow it to rise to 65°C and stir for 3.6 hours. Cool to 0°C, filter, and wash with 1000 ml of deionized water, then with 50 mL×2 ethanol, and dry to obtain 89 g of compound 1 (93%).

Step 2

In a 1L round-bottomed flask, add 400 ml of acetic anhydride and 0.5 g of p-toluenesulfonic acid containing one crystal water. Then 100 g of compound 2 was carefully added under stirring. Insert the drying tube, raise the temperature to 80°C and stir for 2 hours. Cool to 0°C, filter, and wash with anhydrous ether 50 mL × 5 times to obtain a white crystalline solid, namely Dess-Martin hyperiodine reagent 138 g (91%).

Note:

Handle with care to prevent explosion. According to literature recommendations, washing with ethanol can suppress explosions and remove bromate and other impurities as much as possible to reduce the risk of possible explosions.

Precautions:
Filtration and washing should be done quickly and preferably with inert gas protection. Dess-Martin periodinane high iodine reagent will be hydrolyzed when left in humid air.

Oxidation reaction

Oxidant for organic matter to convert certain organic matter into ketones, aldehydes, carboxylic acids and other compounds. For example, it can oxidize primary alcohols to aldehydes or ketones, and reducing agents and nitro compounds to carboxylic acids.

Dehydrogenation reaction

Dehydrogenation reaction to dehydrogenate certain hydrogen-containing compounds to form double bonds or cyclic compounds. For example, it can dehydrogenate alcohols or ketones to aldehydes, imines or cyclic compounds.

Synthesis reaction

Some synthesis reactions, such as the synthesis of aldehyde condensation reactions, the synthesis of aromatic ketones, etc. It can catalyze the transformation of organic matter under appropriate reaction conditions and promote chemical reactions.

Organic Synthesis Laboratory

 

Organic synthesis experiments for oxidation reactions, dehydrogenation reactions and other synthetic reactions. It can help synthetic chemists convert certain organic compounds into target compounds to achieve specific synthetic purposes.

Medicinal Chemistry

 

In medicinal chemistry research, it can be used to synthesize intermediates or structural modules of drugs, thereby realizing the design and development of new drugs. It can introduce specific functional groups or change the molecular structure into synthetic drug molecules to enhance the activity of the drug or improve its properties.

Chemical Production

 

Used in some chemical industries. For example, in the industrial production process of certain organic synthesis reactions, it can be used as a catalyst or oxidant to promote chemical reactions and improve product yield and quality.

It should be noted that when using dess martin its reagent, safe operating procedures should be strictly followed and reaction conditions should be controlled to ensure the safety and efficiency of the laboratory or industrial production process.

In recent years, organic hypervalent iodine compounds have been widely used in modern organic synthesis as new reagents for organic synthesis that are easy to prepare, have mild performance, high selectivity and are environmentally friendly. Dess-Martin hypervalent iodine compound (DMP) is one of the most studied and widely used reagents. Dess-Martin periodinane [also known as Dess-Martin high iodine reagent] is a commonly used, mild, and selective oxidizing reagent. It is often used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Its advantages are mild reaction conditions, moderate speed, low dosage, and simple post-processing.

side effect

This is an important class of organic compounds, typically referring to high iodine reagents such as iodobenzene diacetate (PIDA), (diacetoxyiodide) benzene (DIB), and 2-iodoylbenzoic acid (IBX). These compounds have a wide range of applications in organic synthesis, drug development, and other fields due to their unique oxidative properties. However, with the continuous expansion of its application, the potential side effects of it have gradually received attention. 

Side effect analysis

Skin and mucosal irritation

This is irritating to the skin, and long-term or high concentration exposure may cause symptoms such as redness, swelling, itching, and blisters. This stimulating effect may be related to the oxidative properties of it, which can damage the lipid layer on the skin surface, leading to impaired skin barrier function. Periodic vapors or dust may cause irritation to mucous membranes such as the eyes and nose, leading to symptoms such as tearing, coughing, and sore throat. This stimulating effect may cause mucosal congestion, edema, and even inflammation.

Respiratory irritation and injury

Inhalation of Periodic vapors or dust may cause irritation to the respiratory tract, leading to symptoms such as coughing, sore throat, and difficulty breathing. Long term exposure to the periodic environment may lead to chronic respiratory inflammation and even trigger respiratory diseases such as asthma. Inhaling high concentrations of it vapor may cause lung damage, such as pulmonary edema, pulmonary hemorrhage, etc. This type of injury may cause respiratory failure and even endanger life.

Gastrointestinal discomfort

Ingestion of Periodine or prolonged exposure to its vapors may cause irritation to the gastrointestinal tract, leading to symptoms such as nausea, vomiting, abdominal pain, and diarrhea. This stimulating effect may cause congestion, edema, and even ulceration of the gastrointestinal mucosa. Animal experiments have shown that long-term high-dose intake of Periodine may have toxic effects on the liver, leading to abnormal liver function. This liver toxicity may manifest as symptoms such as elevated transaminase levels and jaundice, and in severe cases may lead to liver failure.

Neurotoxicity

High dose exposure to Periodinane may cause acute neurological symptoms such as dizziness, headache, and confusion. These symptoms may be related to the direct toxic effects of this on the nervous system. Long term exposure to it may have chronic effects on the nervous system, such as decreased motor coordination and impaired learning and memory abilities. This effect may be related to the accumulation of it in the body, leading to gradual impairment of neurological function.

Reproductive and developmental toxicity

Animal experiments have shown that high-dose this med may affect the reproductive function of male animals, such as reduced sperm count and decreased sperm motility. This impact may lead to a decrease in fertility and even infertility. Exposure to Perinane during pregnancy may have adverse effects on fetal development, such as weight loss and skeletal deformities. This developmental toxicity may lead to adverse pregnancy outcomes such as miscarriage and premature birth.

Carcinogenicity and Genotoxicity

There is currently controversy over the carcinogenicity of this. Some studies suggest that it may be carcinogenic, especially under high-dose long-term exposure. However, due to the lack of conclusive human research evidence, its carcinogenic risk still needs further evaluation. In vitro experiments have shown that this may have genotoxicity and can induce DNA damage and chromosomal aberrations. This genotoxicity may increase the risk of genetic diseases such as cancer.

Special population risk

Pregnant and lactating women may have increased sensitivity to it. Long term or high-dose exposure to Periodine may have adverse effects on fetuses or infants. Therefore, it is recommended that pregnant and lactating women avoid contact with this. Children's metabolic and immune systems are not yet fully developed, and their tolerance to it may be low. Long term exposure to this may have adverse effects on the growth and development of children.

Special population risk

Therefore, caution should be exercised when using children's products and foods containing drug. The liver and kidney function of elderly people may decrease, and their metabolism and excretion ability of periodines may be weakened. Long term exposure to Periodine may lead to its accumulation in the body, increasing the risk of side effects. Therefore, elderly people should pay attention to dosage control when using this.

In summary, Periodinane, as a representative compound of the this family, stands out as a superior oxidizing agent in organic synthesis due to its unique structural characteristics and excellent performance. Its stable five-membered ring structure, composed of a high-valent iodine (V) center linked to two acetoxy groups and a benzene ring via oxygen atom bridges, endows it with high stability and selective reactivity. Unlike traditional oxidants, DMP achieves gentle and efficient oxidation of alcohols under mild conditions close to room temperature, without the need for strong acids or heavy metal catalysts, effectively avoiding over-oxidation of primary alcohols to carboxylic acids and environmental pollution caused by toxic by-products. Its remarkable compatibility with sensitive functional groups further expands its application scope, making it an indispensable tool in the synthesis of complex drug intermediates and natural products, where structural integrity and reaction selectivity are critical. By virtue of its high efficiency, selectivity, and mild reaction conditions, DMP has revolutionized the oxidation reaction in organic synthesis, providing a reliable and environmentally friendly solution for researchers, and continuing to play an irreplaceable role in advancing the fields of medicinal chemistry, natural product synthesis, and fine chemical engineering.

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