ChemicalTagger: A tool for semantic text-mining in chemistry

Table 1 Phrases Recognised by ChemicalTagger

Phrase Name	Example
Add-Phrase	Benzoyl peroxide (85 mg) was added to the solution
Apparatus-Action	A 50-ml round-bottom flask sealed with a septum.
Concentrate-Phrase	The filtrate was concentrated under reduced pressure without heating.
Cool-Phrase	The reaction was then cooled to rt.
Degass-Phrase	The solution was purged with argon for 30 min.
Dissolve-Phrase	Salt was dissolved in water.
Dry-Phrase	The yellow product was dried under vacuum.
Extract-Phrase	the products were extracted with diethyl ether (3 × 100 ml).
Filter-Phrase	The solution was filtered through a short silica gel column.
Heat-Phrase	The mixture was heated under reflux for 8 h.
Partition-Phrase	The reaction mixture was partitioned between H2O (100 ml) and EtOAc (400 ml).
Precipitate-Phrase	Precipitating in methanol.
Purify-Phrase	The mixture was purified by column chromatography.
Quench-Phrase	The reaction was quenched with methanol.
Recover-Phrase	The precipitate was recovered by filtration.
Remove-Phrase	The solvent was removed under reduced pressure.
Stir-Phrase	The reaction mixture was stirred at room temperature for 16 h.
Synthesize-Phrase	Synthesis of aromatic polyethers by Scholl reaction.
Wait-Phrase	The mixture was left 2d under stirring.
Wash-Phrase	The resin was washed with DMF.
Yield-Phrase	Chromatography afforded the alcohol 10 as a colourless oil (88 mg, 70%).

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