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179825

Borane dimethyl sulfide complex

Synonym(s):

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

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25 mL
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PLN 429.00
100 mL
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PLN 1,230.00
4 x 25 mL
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PLN 1,240.00
800 mL
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PLN 5,210.00

About This Item

Linear Formula:
(CH3)2S · BH3
CAS Number:
13292-87-0
Molecular Weight:
75.97
UNSPSC Code:
12352112
NACRES:
NA.22
PubChem Substance ID:
24850657
EC Number:
236-313-6
Beilstein/REAXYS Number:
3663489
MDL number:
MFCD00013189

PLN 429.00

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form

liquid

Quality Level

200

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

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.

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

Packaging

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.

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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Borane dimethyl sulfide complex

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Dibromoborane dimethyl sulfide complex

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reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

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

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

functional group

thioether

functional group

thioether

functional group

thioether

functional group

thioether

form

liquid

form

liquid

form

solid

form

liquid

signalword

Danger

Storage Class

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

wgk

WGK 1

flash_point_f

64.4 °F

flash_point_c

18 °C

ppe

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

Hazard Classifications

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2681
SHBQ9982
SHBQ9974
SHBQ4594
STBK8639

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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)
View All Related Papers

Global Trade Item Number

SKUGTIN
179825-18L-C04061838230751
179825-100ML04061838754479
179825-4X25ML04061838754493
179825-800ML04061838754509
179825-25ML04061838754486

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/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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