Borane dimethylsulfide
chemical compound
Borane dimethylsulfide (BMS) is a chemical compound with the chemical formula BH3·S(CH3)2. It is an adduct between borane molecule (BH3) and dimethyl sulfide molecule (S(CH3)2). It is a complexed borane reagent that is used for hydroborations and reductions. The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility. 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. In contrast, BH3·THF requires sodium borohydride to inhibit reduction of THF to tributyl borate (B(OCH2CH2CH2CH3)3). BMS is soluble in most aprotic solvents.
Preparation and structure
Although usually purchased, BMS can be prepared by absorbing diborane into dimethyl sulfide:
B2H6 + 2 S(CH3)2 → 2 BH3·S(CH3)2
It can be purified by bulb to bulb vacuum transfer. Although a structure of BMS has not been determined crystallographically, (pentafluorophenyl)-borane dimethylsulfide (C6F5BH2·S(CH3)2), has been examined by X-ray crystallography. The boron atom adopts a tetrahedral molecular geometry.
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