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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%

Numéro CAS
13292-87-0
Synonymes
BMS
Borane-methyl sulfide

Dimensions Prix ($) Quantité Disponibilité
25ml 47,97
100ml 120,51
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Borane-dimethyl sulfide complex, 94%

MDL
MFCD00013189
EINECS
236-313-6

Propriétés chimiques

Formule
C2H9BS
Poids formulaire
75.97
Point de fusion
-38°
Point d'ébullition
ca 44° dec.
Point d'éclair
-1°(30°F)
Densité
0.801
Indice de réfraction
1.4570
Sensibilité
Air & Moisture Sensitive
Solubilité
Miscible with ethyl ether, dichloromethane, benzene, xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene, methylene chloride and other aprotic solvents.

Applications

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.

Notes

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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H225-H260-H300-H335-H314-H318

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

Mentions de prudence: P210-P231+P232-P260-P261-P301+P310-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3663489
Classe de danger
3
Groupe d'emballage
II
Code tarifaire harmonisé
2942.00
TSCA
Yes
RTECS
PV5080000

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