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192120

Sigma-Aldrich

Borane dimethyl sulfide complex solution

2.0 M in THF

Synonyme(s) :

BMS, Trihydro[thiobis[methane]]boron

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About This Item

Formule linéaire :
(CH3)2S · BH3
Numéro CAS:
13292-87-0
Poids moléculaire :
75.97
Beilstein:
3663489
Numéro MDL:
MFCD00013189
Code UNSPSC :
12352112
ID de substance PubChem :
24851530
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Forme

liquid

Niveau de qualité

200

Pertinence de la réaction

reagent type: reductant

Concentration

2.0 M in THF

Densité

0.855 g/mL at 25 °C

Groupe fonctionnel

thioether

Température de stockage

2-8°C

Chaîne SMILES 

B.CSC

InChI

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

Clé InChI

RMHDLBZYPISZOI-UHFFFAOYSA-N

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Catégories apparentées

Description générale

Borane dimethyl sulfide complex (BMS) acts as a highly efficient and selective reducing agent in the presence of catalytic sodium tetrahydroborate for α-hydroxy esters.[1] Asymmetric borane reduction of a variety of prochiral ketones with BMS using spiroborate esters as catalyst has been reported.[2]

Application

Borane dimethyl sulfide complex (BMS) solution may be used in the following studies:
  • One-pot conversion of alkynes into 1,2-diols.[3]
  • Preparation of iminopentitols.[4]
  • Reduction of representative organic functional groups, such as esters, nitriles and amides.[5]
  • Used along with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.[6]
  • 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 agent

Reactant involved in:
  • Hydroboration / oxidation
Synthesis of cage compounds

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - STOT SE 3 - Water-react 1

Organes cibles

Respiratory system

Risques supp

EUH019

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

1.4 °F - closed cup

Point d'éclair (°C)

-17 °C - closed cup

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
SHBR5604
SHBQ3319
SHBM8590
SHBK2909
STBH6310

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Ana M Gómez et al.
Organic letters, 4(3), 383-386 (2002-02-01)
Primary ozonides derived from alkenyl stannanes display an unusual stability and can be transformed into 1,2-diols by treatment with dimethyl sulfide and borane-methyl sulfide complex. This observation has been incorporated into the development of a novel one-pot strategy for the
Viatcheslav Stepanenko et al.
Tetrahedron letters, 48(33), 5799-5802 (2007-08-13)
Novel spiroborate esters derived nonracemic 1,2-aminoalcohols and ethylene glycol are reported as highly effective catalysts for the asymmetric borane reduction of a variety of prochiral ketones with borane-dimethyl sulfide complex at room temperature. Optically active alcohols were obtained in excellent
M Godskesen et al.
Bioorganic & medicinal chemistry, 4(11), 1857-1865 (1996-11-01)
The four stereoisomeric 1,5-dideoxy-1,5-iminopentitols with D-arabino-(D-lyxo-) (3), ribo- (9), L-lyxo (L-arabino-) (13) and xylo-(18) configurations were synthesized. The corresponding aldonolactones (1, 7 and 11) or aldonic acid ester (15b) having a leaving group at C-5 gave by reaction with aqueous
Selective reductions. 29. A simple technique to achieve an enhanced rate of reduction of representative organic compounds by borane-dimethyl sulfide.
Brown HC, et al.
The Journal of Organic Chemistry, 47(16), 3153-3163 (1982)
Highly Enantioselective Borane Reduction of Prochiral Ketones Catalyzed by C3-Symmetric Tripodal β-Hydroxy Amides
Fang T, et al.
Synlett, 1559-1559 (2006)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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