F Pentylamine

Slaughter, T.F., Achyuthan, K.E., Lai, T.-S., and Greenberg, C.S. (1992) A microtiter plate transglutaminase assay utilizing 5-(biotinamido)pentylamine as substrate. Anal. Biochem. 205, 1-6. 

Hydroperoxides and peroxides oxidize primary and secondary aliphatic amines to imines. Thus f-butyl hydroperoxide oxidizes 4-methyl-2-pentyl-amine to 2-(4-methylpentylidene)-4-methyl-2-pentylamine in 66% yield [29]. Di-r-butyl peroxide reacts in a similar manner [29]. However, this reaction is... 

PENTYLAMINE or n-PENTYLAMINE (110-58-7) Forms explosive mixture with air (flash point 30°F/- 1°C also reported at 45°F/7°C oc). A weak base. Keep away from heat, sunlight. Incompatible with strong oxidizers, acids, organic anhydrides, isocyanates, vinyl acetate, acrylates, substituted allyls, alkylene oxides, epichlorohydrin, ketones, aldehydes, alcohols, glycols, phenols, cresols, caprolactum solution. May accumulate static electrical charges, and may cause ignition of its vapors. 

Pyridine can become involved in nucleophilic substitution when very reactive trifiates are being synthesized. One approach to minimize this disadvantage is to replace it with sterically hindered bases, such as 2,6-di-f-butyl-4-methylpyridine, 2,4,6-trisubs-tituted pyrimidines, or nonnucleophilic aliphatic amines (usually W,W-diisobutyl-2,4-dimethyl-3-pentylamine). No salt formation appears to take place under these conditions. The triflic anhydride seems to be the direct triflating agent and the base only neutralizes the triflic acid formed. Numerous alkyl triflates have been prepared in the literature by the above method. Some recent examples of triflates prepared from alcohols are illustrated in eqs 2 and 3. As an exception, 2,6-dinitrobenzyl alcohol does not react with Tf20 although similar sulfonyl esters could be prepared. ... 

Other bases such as pyridine, lutidine, EtsN, polymer-bound 2,6-di-f-butyl-4-methylpyridine, and 2,4,6-trialkyl-sub-stituted pyrimidines were also used. The commercially available 7V,A-diisobutyl-2,4-dimethyl-3-pentylamine is a very convenient base to prepare the vinyl triflates. In the case of nonfunction-alized ketones, anhydrous Na2C03 has been proved to be very successful. ... 

---