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Merck

179825

Sigma-Aldrich

Borane dimethyl sulfide complex

Sinónimos:

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

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25 ML
MXP 1,892.00
100 ML
MXP 5,112.00
4 X 25 ML
MXP 5,148.00
800 ML
MXP 23,064.00

MXP 1,892.00


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Fórmula lineal:
(CH3)2S · BH3
Número CAS:
Peso molecular:
75.97
Beilstein/REAXYS Number:
3663489
EC Number:
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22

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form

liquid

Quality Level

reaction suitability

reagent type: reductant

density

0.801 g/mL at 25 °C (lit.)

functional group

thioether

storage temp.

2-8°C

SMILES string

B.CSC

InChI

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

Inchi Key

RMHDLBZYPISZOI-UHFFFAOYSA-N

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Este artículo
192120255106262064
reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

density

0.801 g/mL at 25 °C (lit.)

density

0.855 g/mL at 25 °C

density

-

density

1.347 g/mL at 25 °C

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

form

liquid

form

liquid

form

solid

form

liquid

functional group

thioether

functional group

thioether

functional group

thioether

functional group

thioether

General description

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]

Packaging

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

Other Notes

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

Legal Information

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

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Danger

Hazard Classifications

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

Clase de almacenamiento

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

wgk_germany

WGK 1

flash_point_f

64.4 °F

flash_point_c

18 °C

ppe

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


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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)
Borane Dimethyl Sulfide
Zaidlewicz M, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)

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/418/501/product-dating-information-06-25-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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