BCAT

Description

BCAT (benzotriazole-1-carboxamidinium tosylate) is an organic synthesis reagent used to convert primary and secondary amines to guanidines. The reaction takes place under mild conditions with good to moderate product yields for a wide range of substrates, which makes the reagent a convenient tool in medicinal chemistry, where the guanidine group is included in the structure of many medicinal substances. The guanidine fragment is present in the structure of a number of known pharmacologically active compounds - from antihypertensive drugs to antimicrobial and antiparasitic agents, which explains the constant interest of synthetic chemistry in convenient methods of its administration.

Basic Attributes

• CAS No: 163853-10-9
• Chemical formula: C14H15N5O3S
• Molecular weight: 333.37
• Exact weight: 333.089569
• EU number: 1533716-785-6
• PSA Specifications: 143.33000
• XLogP3: 3.29540

Mechanism of action of the reagent

The molecule consists of a benzotriazole moiety linked to a carboxamidinium group and a tosylate counterion. The carboxamidinium group acts as an electrophilic center: when interacting with an amine, nucleophilic substitution of the benzotriazole fragment occurs with the formation of guanidine. This mechanism for converting amines into guanidines is considered a more convenient alternative to previous synthesis methods. The reaction byproduct, benzotriazole, is easily removed during the purification step, making the isolation of the target guanidine easier than techniques that use more difficult-to-volatile or toxic leaving groups.

Scope of application

It is used in laboratory practice of organic and medicinal chemical synthesis to obtain guanidine derivatives from a wide range of primary and secondary amines.

Safety Information

• Hazard Statement: H315 (causes skin irritation)
• Precautions: P261, P264, P271, P280, P302 + P352, P304 + P340, P305 + P351 + P338, P312, P321, P332 + P313, P337 + P313, P362, P403 + P233, P405, P501

Storage and handling

According to notification in the ECHA C&L Inventory register from 1 company, the H315 classification was confirmed for 100% of cases. There is no data on melting point, solubility, vapor pressure, transport codes and LD50 values ​​in the dump; no additional information was found in open sources - these items are not filled in to avoid entering false values. Store in a dry place, use skin and eye protection when working. The moderately high value of the polar surface area (PSA 143.33000) reflects the presence of several nitrogen-containing functional groups in the benzotriazole and amidine fragments of the molecule.

Implications for medicinal chemistry

The advent of convenient and selective guanylating reagents like BCAT has simplified the synthesis of guanidine derivatives during the development of new drug candidates, from antihypertensive and antiarrhythmic agents to antiparasitic and antimicrobial compounds, in which the guanidine group often provides a key interaction with the biological target. The tosylate counterion ensures sufficient stability and solubility of the reagent when stored under laboratory conditions.