The tests recorded pressure rise rates below the instrument's calibrated threshold, hence were thought to be negative for potential explosivity . UN Dangerous Goods Test 3a (ii) BAM Fall Hammer impact testing of 6 and 7 at 60J resulted in decomposition, producing a change in both materials' color and an odor without flame or explosion. The decomposition observed may be due to the impact test generating enough heat to reach each material's low thermal onset at 79 °C and 84 °C, respectively, to catalyze their exothermic decomposition. During the many gramscale batch runs using 6 and 7 (vide supra) no hazardous events were observed. However, in order to preemptively address potential concerns on scale, reagent 6 was tested on even larger scale using a flow setup (Figure ). Thus, chlorination of celecoxib analogue (53) was pursued in flow at 20 gram-scale. A separate substrate specific optimization was pursued in order to increase the reaction rate and subsequent potential throughput of the reaction. The reaction rate was sensitive to both temperature and solvent composition where the conditions shown in Figure were found to provide >95% conversion in 25 minutes. From these optimized conditions a flow experiment was designed wherein 20 grams of 53 was converted to the desired product over 130 minutes in flow with 82% isolated yield. Observations from the lab-scale demonstration in flow determined that the reaction could be further scaled with minimal consideration.