Borane-dimethyl sulfide complex

• Catalog No.: L07705
• CAS Number: 13292-87-0
• M. F.: C2H9BS
• M. W.: 75.96886
• Purity: 94%

SYNONYMS

• Title: 硼烷二甲基硫醚
• IUPAC name: (methylsulfanyl)methane borane
• IUPAC Traditional name: dimethyl sulfide borane
• Synonyms: BMS; Borane-methyl sulfide

DATABASE IDS

• Beilstein Number: 3663489
• EC Number: 236-313-6
• MDL Number: MFCD00013189
• CAS Number: 13292-87-0

PROPERTIES

• Purity: 94%
• Boiling Point: ca 44°C dec.
• Density: 0.801
• Flash Point: -1°C(30°F)
• Melting Point: -38°C
• Refractive Index: 1.4570
• GHS Hazard statements: H225-H260-H301-H335-H314-H318
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P280-P305+P351+P338-P309+P311-P370+P378I-P402+P404
• Risk Statements: 11-14/15-25-37/38-41
• RTECS: PV5080000
• Safety Statements: 16-23-26-36/37/39-43-45
• Storage Warning: Air & Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2924
• Packing Group: II

REFERENCES

• Stable, convenient reagent for a wide range of reduction and hydroboration reactions. Reviews: Org. Prep. Proced. Int., 13, 225 (1981); Chem. Rev., 76, 773 (1976); A. Pelter et al, Borane Reagents, Academic Press, N.Y. (1988).
• Carboxylic acids are readily reduced to alcohols: J. Org. Chem., 38, 2786 (1973).
• Conditions for reduction of amino acids to amino alcohols without racemization are described for L-valine: Org. Synth. Coll., 7, 530 (1990).
• By use of refluxing THF as solvent, the reduction can be extended to include esters, primary, secondary and tertiary amides and nitriles: J. Org. Chem., 47, 1389 (1982); Synth. Commun., 21, 1579 (1991).
• The selectivity of BMS in reducing free acids more rapidly than esters is reversed in the case of monoesters of malonic acids. The borane binds initially to the acid function, but reduces the ester group intramolecularly: Tetrahedron Lett., 30, 6687 (1989):
  
• For a discussion of the effect of the alkene structure on hydroboration with borane dimethyl sulfide, see: J. Org. Chem., 48, 644 (1983). For cis-anti-Markovnikov hydration of alkenes by hydroboration with BMS, followed by H₂O₂ oxidation of the borane, see: J. Org. Chem., 39, 1437 (1974).