The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium. Fullerenes are soluble in many organic solvents, such as toluene, chlorobenzene, and 1,2,3-trichloropropane. It is prepared from the reaction of chlorobenzene, PCl, and sodium. Thiophenol can be manufactured from chlorobenzene and hydrogen sulfide over alumina at . Reactions are typically conducted in chlorobenzene solution. Fullerene reacts with chlorobenzene and aluminium chloride in a Friedel-Crafts alkylation type reaction. Products include&colon; aniline, caustic soda, chlorine, chlorobenzene, nitrochlorobenzene, nitrobenzene, vinyl chloride monomer (VCM). For example, this approach is used to convert toluene into toluidines and chlorobenzene into 4-chloroaniline. Dow's Process may also refer to the hydrolysis of chlorobenzene in the preparation of phenol. The aryl halides produced on the largest scale are chlorobenzene and the isomers of dichlorobenzene. Benzene can be easily converted to chlorobenzene by electrophilic aromatic substitution. The bacterium "Rhodococcus phenolicus" degrades chlorobenzene as sole carbon sources. A chlorobenzene reductive dehalogenase has also been identified in the strain CBDB1. First, m-cresol, chlorobenzene, sodium hydroxide, potassium hydroxide, and copper chloride react to yield m-phenoxytoluene. Chlorobenzene exhibits "low to moderate" toxicity as indicated by its of 2.9 g/kg.