(methylsulfanyl)methane borane

• ChemBase ID: 139969
• Molecular Formular: C2H9BS
• Molecular Mass: 75.96886
• Monoisotopic Mass: 76.05180169
• SMILES: B.CSC
• Canonical SMILES: CSC.B
• InChI: InChI=1S/C2H6S.BH3/c1-3-2;/h1-2H3;1H3
• InChIKey: RMHDLBZYPISZOI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (methylsulfanyl)methane borane
• IUPAC Traditional name: dimethyl sulfide borane
• Synonyms: (Dimethyl sulfide)trihydroboron; BMS; Borane-dimethyl sulfide; Borane dimethyl sulfide complex; Trihydro[thiobis[methane]]boron; Borane dimethyl sulfide complex solution; Borane methyl sulfide complex; Dimethyl sulfide borane; Borane-methyl sulfide; Borane-dimethyl sulfide complex; Borane-dimethyl sulfide complex, 2M in toluene; Borane-dimethyl sulfide complex, 2M in THF; Borane-dimethyl sulfide complex, nominally 5M in ether; Borane-Methyl sulfide coMplex; 硼烷二甲基硫醚络合物; 硼烷二甲基硫醚络合物 溶液; 硼烷二甲硫醚; 硼烷甲基硫醚络合物; 硼烷二甲基硫醚; 硼烷二甲基硫醚络合物,2M甲苯溶液, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲基硫醚络合物, 2M 四氢呋喃溶液, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲基硫醚络合物, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲基硫醚络合物, 通常 5M乙醚溶液, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲硫醚络合物

Database IDs

• CAS Number: 13292-87-0
• EC Number: 236-313-6
• MDL Number: MFCD00013189
• Beilstein Number: 3663489
• PubChem SID: 24849576; 162234215; 24851577; 24851529; 24850657; 24851335; 24851530; 24868320
• PubChem CID: 9833925

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.2235795
• LogD (pH = 7.4): 1.2235795
• Log P: 1.2235795
• Molar Refractivity: 18.8917 cm^3
• Polarizability: 7.4785047 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Melting Point: -38°C
• Boiling Point: ~34 °C; ca 44°C dec.
• Flash Point: 1.4 °F; -1°C(30°F); -1°C(31°F); -17 °C; -17°C(-1°F); 18 °C; -31 °F; -35 °C; -35°C(-31°F); -40 °C; -40 °F; 44.6 °F; 64.4 °F; 7 °C; 7°C(45°F)
• Density: 0.74 g/mL at 25 °C; 0.789; 0.789 g/mL at 25 °C; 0.801; 0.801 g/mL at 20 °C(lit.); 0.801 g/mL at 25 °C(lit.); 0.855; 0.855 g/mL at 25 °C; 0.856; 0.856 g/mL at 25 °C; 1.287 g/mL at 25 °C
• Refractive Index: 1.4570

Safety Information

• Storage Warning: Air & Moisture Sensitive
• RTECS: PV5080000
• European Hazard Symbols: Flammable (F); Highly flammable (F+); Toxic (T); X; Irritant (Xi); Harmful (Xn)
• UN Number: 3398; 3399; UN2924; UN3399
• German water hazard class: 1; 3
• Hazard Class: 3; 4.3
• Packing Group: 1; 2; I; II
• Risk Statements: 11-14/15-19-22-37/38-41; 11-14/15-19-37-41; 11-14/15-22-38-41-48/20-63-67; 11-14/15-25-37/38-41; 11-14/15-36-40; 11-14/15-37/38-41; 12-14/15-19-20/22-37/38-41-67; 12-14/15-19-22-37/38-41-67; 12-14/15-19-22-38-41-67; 63-11-14/15-38-41-48/20-65-67
• Safety Statements: 16-23-26-33-36/37/39-43; 16-23-26-33-36/39; 16-23-26-36/37/39-43-45; 16-26-29-33-36/37/39-43; 16-26-36/37/39-43-62; 16-26-36/37-43; 16-26-39-43
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H224-H260-H302-H315-H318-H335-H336; H224-H260-H315-H318-H335-H336; H224-H261-H314-H318-H302-H336; H225-H260-H301 + H311-H315-H318-H335; H225-H260-H301-H335-H314-H318; H225-H260-H302 + H312-H304-H315-H318-H336-H361d-H373; H225-H260-H315-H318-H335; H225-H260-H318-H315-H361-H373-H302-H336; H225-H261-H318-H315-H302-H335; H225-H261-H318-H351
• GHS Precautionary statements: P210-P223-P231 + P232-P261-P370 + P378-P422; P210-P231 + P232-P280-P305 + P351 + P338-P422; P210-P280-P243-P305+P351+P338-P370+P378I-P402+P404; P210-P280-P305+P351+P338-P309+P311-P370+P378I-P402+P404; P280-P305+P351+P338-P301-P315-P370+P378I-P402+P404
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3398 4.3/PG 2; UN 3399 4.3/PG 1
• Supplemental Hazard Statements: May form explosive peroxides., Reacts violently with water.; Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: 94%
• Concentration: ~5 M in diethyl ether; >90% in dimethyl sulfide; 1.0 M in methylene chloride; 2.0 M in diethyl ether; 2.0 M in THF; 2.0 M in toluene; 2M in THF; 2M in toluene; 5.0 M in diethyl ether; nominally 5M in ether
• Grade: purum; technical
• Packaging: packaged under Argon in resealable ChemSeal? bottles
• Linear Formula: (CH3)2S · BH3

DETAILS

Sigma Aldrich - 447145

Packaging
100 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

Sigma Aldrich - 179825

Application
Reagent for hydroboration reduction and other applications.1,2
Used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones. CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols. Highly enantioselective reduction of ketones catalyzed by C3-symmetric tripodal hydroxyamides.
Other Notes
10.0-10.2 M as BH3. May contain excess methyl sulfide.
Packaging
25, 4×25, 100, 800 mL in Sure/Seal™
8, 18 L in Kilo-Lab™
View returnable container options.

Sigma Aldrich - 194824

Packaging
100, 800 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

Sigma Aldrich - 15587

Other Notes
Convenient and stable source of borane for hydroborations, reviews 6,7,8; Selective reduction of α-hydroxyesters9
Packaging
25, 100 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4
• Synthesis of cage compounds5

Sigma Aldrich - 193038

Packaging
100, 800 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

Sigma Aldrich - 192120

Application
Used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.6 CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to chiral 1,3-diols.7 Highly enantioselective reduction of ketones catalyzed by C3-symmetric tripodal hydroxyamides.8
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5
Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 192112

Packaging
100, 800 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

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).