Accéder au contenu
MilliporeSigma
Toutes les photos(2)

Principaux documents

Voir toute la documentation

179825

Sigma-Aldrich

Borane dimethyl sulfide complex

Synonyme(s) :

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

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme

Sélectionner une taille de conditionnement

25 ML
106,00 $
4 X 25 ML
216,00 $
100 ML
321,00 $
800 ML
1 250,00 $
18 L
13 530,00 $

106,00 $

En stockDétails

Devis pour commande en gros
Toutes les photos(2)

Sélectionner une taille de conditionnement

Changer de vue
25 ML
106,00 $
4 X 25 ML
216,00 $
100 ML
321,00 $
800 ML
1 250,00 $
18 L
13 530,00 $

About This Item

Formule linéaire :
(CH3)2S · BH3
Numéro CAS:
13292-87-0
Poids moléculaire :
75.97
Beilstein:
3663489
Numéro CE :
236-313-6
Numéro MDL:
MFCD00013189
Code UNSPSC :
12352112
ID de substance PubChem :
24850657
Nomenclature NACRES :
NA.22

106,00 $

En stockDétails

Devis pour commande en gros

Forme

liquid

Niveau de qualité

200

Pertinence de la réaction

reagent type: reductant

Densité

0.801 g/mL at 25 °C (lit.)

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

Catégories apparentées

Description générale

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.[1][2]

Application

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.[3]
  • For the conversion of ozonides to alcohols.[4]
  • In the CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols.[5]
  • For enantioselective reduction of ketones to chiral secondary alcohols in the presence of C3-symmetric tripodal hydroxyamide as a ligand.[6]
  • For the hydroboration reduction and other applications.[7][8]
  • With a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.[9]

Conditionnement

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.

Autres remarques

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

Informations légales

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

Mention d'avertissement

Danger

Classification des risques

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

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)

64.4 °F

Point d'éclair (°C)

18 °C

Équipement de protection individuelle

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

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
SHBL1345
SHBQ9982
SHBQ9974
SHBM1643
SHBQ4594

Vous ne trouvez pas la bonne version ?

Si vous avez besoin d'une version particulière, vous pouvez rechercher un certificat spécifique par le numéro de lot.

Rechercher un(e) COA

Déjà en possession de ce produit ?

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

Consulter la Bibliothèque de documents

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)
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)
Borane Dimethyl Sulfide
Zaidlewicz M, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)
Afficher tous les articles scientifiques apparentés

Questions

1–2 of 2 Questions  

  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

      Helpful?

  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

      Helpful?

Reviews

No rating value

Active Filters

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique