454653-24-8

Usage

Type of compound

Trifluoro derivative of triazine

Common use

Reagent in organic synthesis

Known for

Activating carboxylic acids for amide bond formation

Applications

a. Peptide and protein chemistry
b. Synthesis of pharmaceuticals
c. Synthesis of agrochemicals

Reagent efficiency

Versatile and efficient for amide bond formation in organic chemistry

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 1075-59-8 2-hydroxy-4,6-dimethoxy-1,3,5-triazine 
• 1075-59-8 2-hydroxy-4,6-dimethoxy-1,3,5-triazine 

Relevant academic research and scientific papers

Primary-amine-specific lactamization of ω-amino acids by an artificial cyclotransferase based on [18] crown-6

Feet first: Carboxylic acids with a primary amino group in the farthest position from the carboxy group are specifically bound to an artificial cyclotransferase based on [18]crown-6. The amino group fits into the [18]crown-6 substrate-binding site to bring the carboxyl group close to the 2-ammonio-1,3,5-triazine reaction site for selective conversion into a lactam. (Chemical Equation Presented)

Labeling study of avidin by modular method for affinity labeling (MoAL)

We studied the specific labeling of avidin with biotinylated modular ligand catalysts via MoAL, which we recently established. The labeling yield was found to depend on the linker length connecting the catalytic site to biotin in the modular ligand catalyst 1, and the maximum yield was obtained with 1d possessing octamethylene linker. The labeling reaction reached a maximum rate with only 4 equiv of the ligand catalyst. Presumably, all the subunits of avidin with homotetrameric structure formed a stable complex with 4 equiv of the catalyst because of the extremely high affinity. The ligand catalyst bound to avidin first catalyzed N-triazinylation of the -amino group of Lys111, and the resulting regenerated catalyst then catalyzed the reaction of Asp108 and CDMT.

DEHYDRATING CONDENSATION AGENT HAVING PROPERTY OF ACCUMULATING AT INTERFACE WITH WATER

The present invention provides a 1,3,5-triazine compound represented by the following formula I: This compound can be synthesized easily and more economically and can be used as a dehydrating condensing agent having the property of accumulating at a water interface. In the case where carboxylic acid, amine, alcohol or other reaction substrate is amphiphilic, when mixing the dehydrating condensing agent of the present invention, which is amphiphilic, and the substrate to form various molecular aggregate phase including micelles in an aqueous solution, the substrate and the dehydrating condensing agent can be accumulated at the water interface. As a result, the concentration of the substrate increases locally at the water interface, and condensation reaction can be performed extremely efficiently.

Unusual rate enhancement of bimolecular dehydrocondensation to form amides at the interface of micelles of fatty acid salts

(Chemical Equation Presented) Speeding up: A micelle-water interface acts as a suitable reaction field for dehydrocondensation. The coupling reaction of fatty acid salts with a triazine-type amphiphilic dehydrocondensing agent in a micellar system (see picture) underwent up to 2000-fold acceleration. The rate enhancement can be attributed to the higher local concentration and preorientation of the reactants in the micelles.

Approach to green chemistry of DMT-MM: Recovery and recycle of coproduct to chloromethane-free DMT-MM

A simple procedure for the isolation of 2-hydroxy-4,6-dimethoxy-1,3,5-triazine (HO-DMT), a coproduct arising from dehydrating condensation using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) has been established. HO-DMT can be recycled by treatment with POCl3 to give 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), which is further converted to DMT-MM. Alternatively, reaction with triflic anhydride followed by addition of N-methylmorpholine gives DMT-MM triflate.