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13292-87-0 - Borane-dimethyl sulfide complex, 94% - BMS - Borane-methyl sulfide - L07705 - Alfa Aesar

L07705 Borane-dimethyl sulfide complex, 94%

Número CAS
13292-87-0
Nombre Alternativo
BMS
Borane-methyl sulfide

Tamaño Precio ($) Cantidad Disponibilidad
25ml 52,20
100ml 119,00
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Borane-dimethyl sulfide complex, 94%

MDL
MFCD00013189
EINECS
236-313-6

Propiedades químicas

Fórmula
C2H9BS
Peso molecular
75.97
Punto de fusión
-38°
Punto de ebullición
ca 44° dec.
Punto de inflamabilidad
-1°(30°F)
Densidad
0.801
Índice de refracción
1.4570
Sensibilidad
Air & Moisture Sensitive
Solubilidad
Miscible with ethyl ether, dichloromethane, benzene, xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene, methylene chloride and other aprotic solvents.

Aplicaciones

Borane- dimethyl sulfide is used for hydroboration and reduction reactions. It is used in the reduction of aldehydes, ketones, epoxides and carboxylic acids to give corresponding alcohols. It is also involved in the Corey-Itsuno reduction. It acts as an intermediate in the preparation of highly pure semiconductor. It is also employed as a rocket propellant.

Notas

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Store in a cool place. Incompatible with acids, water, alcohols, bromine, acid anhydrides, acid chlorides and oxidizing agents.

Referencias documentales

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).

James, S. N.; Coster, M. J. Synthesis of N-alkylsulfonamides by borane-dimethyl sulfide reduction of N-acylsulfonamides. Tetrahedron Lett. 2015, 56 (16), 2059-2061.

Xie, Z.; Zhou, T.; Gou, Y. Synthesis and characterization of zirconium diboride ceramic precursor. Ceram. Int. 2015, 41 (5), 6226-6231.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H225-H260-H300-H314-H318-H335

Highly flammable liquid and vapour. In contact with water releases flammable gases which may ignite spontaneously. Fatal if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage. May cause respiratory irritation.

Indicaciones de precaución: P223-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from any possible contact with water, because of violent reaction and possible flash fire. IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
3663489
Clase de peligro
3
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2942.00
TSCA
Yes
RTECS
PV5080000

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