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Sigma-Aldrich

Borane dimethyl sulfide complex

Sinonimo/i:

(Dimethyl sulfide)trihydroboron, BMS, Borane-dimethyl sulfide

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About This Item

Formula condensata:
(CH3)2S · BH3
Numero CAS:
13292-87-0
Peso molecolare:
75.97
Beilstein:
3663489
Numero CE:
236-313-6
Numero MDL:
MFCD00013189
Codice UNSPSC:
12352112
ID PubChem:
24850657
NACRES:
NA.22

Forma fisica

liquid

Impiego in reazioni chimiche

reagent type: reductant

Densità

0.801 g/mL at 25 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

B.CSC

InChI

1S/C2H6S.BH3/c1-3-2;/h1-2H3;1H3
RMHDLBZYPISZOI-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

Borane dimethyl sulfide complex (BMS) is a commonly used reagent and a mediator for hydroboration reaction for the preparation of organoborane compounds, which are utilized as key intermediates in organic synthesis. BMS is also employed as a reducing agent for the reduction of various functional groups such as aldehydes, ketones, epoxides, esters, and carboxylic acids to corresponding alcohols.

Applicazioni

Borane-dimethyl sulfide (BH3 Me2S) can be used as a reagent:
  • For the selective synthesis of 1,3,5-oxygenated compounds from dimethyl 3-oxoglutarate.
  • For the conversion of ozonides to alcohols.
  • In the CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols.
  • For enantioselective reduction of ketones to chiral secondary alcohols in the presence of C3-symmetric tripodal hydroxyamide as a ligand.
  • For the hydroboration reduction and other applications.
  • With a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.

Confezionamento

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
View returnable container options.

Altre note

10.0-10.2 M as BH3. May contain excess methyl sulfide.

Note legali

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Avvertenze

Danger

Classi di pericolo

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - Water-react 1

Codice della classe di stoccaggio

4.3 - Hazardous materials which set free flammable gases upon contact with water

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

64.4 °F

Punto d’infiammabilità (°C)

18 °C

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificati d'analisi (COA)

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Efficient synthesis of 1, 3, 5-oxygenated synthons from dimethyl 3-oxoglutarate: first use of borane-dimethyl sulfide complex as a regioselective reducing agent of 3-oxygenated glutarate derivatives
Riatto VB, et al.
Journal of the Brazilian Chemical Society, 22(1), 172-175 (2011)
Study of Hydroboration of (μ-H)2Os3(CO)10 with Various Borane Complexes(BH3?L: L=Lewis base)
Chung JH
J. Korean Chem. Soc., 47, 675-678 (2003)
Highly catalytic enantioselective reduction of aromatic ketones using chiral polymer-supported Corey, Bakshi, and Shibata catalysts
Degni S, et al.
Tetrahedron Asymmetry, 15, 1495-1499 (2004)
Generation of bis (pentafluorophenyl) borane-dimethyl sulfide complex as a solution of hexane and its application to hydroboration of alk-1-yne with pinacolborane
Hoshi M, et al.
Tetrahedron Letters, 48(48), 8475-8478 (2007)
A convenient method for the reduction of ozonides to alcohols with borane-dimethyl sulfide complex
Flippin LA, et al.
The Journal of Organic Chemistry, 54(6), 1430-1432 (1989)
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