General Description

Bromodiphenylmethane is a white crystalline solid with limited solubility in water but can dissolve in organic solvents. It falls under the diphenylmethane family. This compound is odorless, stable under normal conditions, but can decompose when exposed to strong oxidizing agents or acids. Bromodiphenylmethane is used as an intermediate in the synthesis of Modafinil, a medication for sleep disorders. It is also used as a reagent in the synthesis of O-(triazolyl)methyl carbamate, which inhibits FAAH. Safety precautions include wearing protective equipment, avoiding inhalation, and following proper handling procedures.

Figure 1. Bromodiphenylmethane

Properties

Bromodiphenylmethane, with a molecular weight of 257.1 g/mol, is a crystalline solid that appears white or off-white in color. It falls under the diphenylmethane family. While it has limited solubility in water, it can dissolve in various organic solvents such as ethanol, ether, and benzene. This compound is typically odorless and remains stable under normal storage and handling conditions. However, it is important to note that bromodiphenylmethane may decompose or react when exposed to strong oxidizing agents or acids. Its melting point range is between 85-87°C, and it has a high boiling point of 184°C under a pressure of 20 mm Hg. The density of this compound is approximately 0.9 g/cm3, and its estimated refractive index stands at 1.6290. At 25°C, bromodiphenylmethane exhibits a vapor pressure of 0.000358 mmHg. Although bromodiphenylmethane holds potential for industrial applications, caution must be exercised due to its properties. ¹

Applications

Bromodiphenylmethane has important applications in various fields due to its chemical properties. One of its primary uses is as an intermediate in the synthesis of Modafinil, a medication used to treat sleep disorders such as narcolepsy and sleep apnea. Modafinil is developed by the French company Lafon and is a central nervous system stimulant drug. It was first marketed in France in 1994 and has since gained global popularity as a cognitive enhancer. In addition to its use in pharmaceuticals, bromodiphenylmethane is also used as a reagent in the synthesis of O-(triazolyl)methyl carbamate, which is a novel and effective inhibitor of fatty acid amide hydrolase (FAAH). FAAH is an enzyme involved in the metabolism of endocannabinoids, which are neurotransmitters that play a role in pain regulation and cognitive function. Inhibiting FAAH activity can lead to increased levels of endocannabinoids, which may have therapeutic potential for conditions like anxiety and chronic pain. Overall, bromodiphenylmethane is an important compound used in the synthesis of pharmaceuticals and other organic compounds. Its unique chemical properties make it a valuable reagent in the development of new drugs, which can have beneficial effects on human health and quality of life. ²

Safety

Bromodiphenylmethane is a highly corrosive substance that can cause severe harm to various organs and bodily systems. To ensure safety when working with bromodiphenylmethane, several guidelines must be followed. Firstly, it is crucial to wear appropriate personal protective equipment, such as gloves, goggles, and suitable clothing to prevent skin and eye contact. Additionally, it is important to avoid inhaling any dust, vapor, mist, or gas produced by bromodiphenylmethane. This can be achieved by working in well-ventilated areas. In case of contact with the eyes, immediate flushing with water for at least 30 minutes is necessary, followed by seeking medical help. If bromodiphenylmethane comes into contact with the skin, washing the affected area with plenty of water for at least 15 minutes is recommended. Contaminated clothing should also be removed and washed before reuse. When handling bromodiphenylmethane in the event of a fire, it is crucial to use dry chemical, carbon dioxide, or appropriate foam for firefighting. Water should be avoided as it can react with the substance and produce corrosive vapors. Finally, bromodiphenylmethane should only be used in well-ventilated areas, and the container should be tightly closed when not in use. It should be stored in a secure location. ³

Reference

1. Benzene, 1,1'-(bromomethylene)bis-. NIST Chemistry WebBook.

2. Galun AB, Kalir A. p-Bromodiphenylmethane. Organic Syntheses, 2003.

3. Material Safety Data Sheet: Bromodiphenylmethan. Coleparmer, 2005, Catalog Numbers: AC106900000.