Borane dimethylsulfide

[1] BMS is commercially available at much higher concentrations than its tetrahydrofuran counterpart (10 M) and does not require sodium borohydride as a stabilizer, which could result in undesired side reactions.

Although a structure of BMS has not been determined crystallographically, (pentafluorophenyl)-borane dimethylsulfide (C6F5BH2·S(CH3)2), has been examined by X-ray crystallography.

[5] In hydroborations with BMS, the dimethylsulfide dissociates in situ, liberating diborane, which rapidly adds to the unsaturated bonds.

Activation by the nitrogen of the chiral oxazaborolidine[clarification needed] catalyst of the stoichiometric reducing agent allows for asymmetric control of the reagent.

[clarification needed] In general BMS does not lead to significantly greater enantiomeric selectivities than borane-THF, however its increased stability in the presence of moisture and oxygen makes it the reagent of choice for the reduction.