Tricaprylmethylammonium Chloride

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A colorless, odorless solid which is readily soluble in water. It is used as a phase transfer catalyst and as an extraction reagent in the synthesis of extended p-systems and other aromatic aldehydes. It is also useful in the Suzuki-Miyaura cross-coupling reaction. When heated to decomposition, it produces toxic fumes of NOx, NH3 and Cl-.

This article is part of the Chemistry in Context series, a collection of articles that provide context for important chemical concepts through definitions, illustrations, and discussion questions. It is intended for use in high school and college chemistry courses as well as for general interest.

The chloride ion is important in many aspects of normal body physiology and is involved in cellular respiration, electrolyte balance and fluid balance. Its concentration in extracellular fluid is influenced by several variables including acid-base imbalance, renal and hepatic function and metabolic states.

Overdosage can cause a serious degree of acidosis, confusion and coma and requires immediate treatment with a hyperchloremic solution to correct the condition. Intravenous administration of ammonium chloride is contraindicated in patients with severe impairment of renal or hepatic function, in cardiac edema and in those who have developed metabolic acidosis due to vomiting of hydrochloric acid (with associated loss of sodium). It is also a poor choice in the presence of metabolic alkalosis with hypotonic shock as it causes an increased risk for intravascular volume expansion and pulmonary edema. During infusion of the compound, monitor the patient for signs and symptoms of a hyperchloremic response such as nausea, vomiting or confusion.

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