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Sigma-Aldrich

Borane dimethyl sulfide complex solution

greener alternative

1.0 M in 2-methyltetrahydrofuran

Synonym(s):

BMS, Trihydro[thiobis[methane]]boron

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About This Item

Linear Formula:
(CH3)2S · BH3
CAS Number:
13292-87-0
Molecular Weight:
75.97
Beilstein:
3663489
MDL number:
MFCD00013189
UNSPSC Code:
12352112
PubChem Substance ID:
329767736
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: reductant

greener alternative product characteristics

Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

concentration

1.0 M in 2-methyltetrahydrofuran

density

0.844 g/mL at 25 °C

greener alternative category

, Aligned

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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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product, 1.0 M in 2-methyltetrahydrofuran aligns with "Safer Solvents and Auxiliaries", "Use of Renewable Feedstocks" and "Inherently Safer Chemistry for Accident Prevention". Find details here.

Application

2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry
Commonly used in hydroboration of olefins and as a reductant of carbonyls. 2-Me-THF has shown potential as an environmentally friendly solvent compared to commonly used solvents; e.g. dichloromethane and THF.
For an alternative to Tetrahydrofuran and Dichloromethane, please see: An alternative to Tetrahydrofuran and Dichloromethane
Reactant used as a regioselective reducing agent

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

Packaging

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

Legal Information

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - Skin Irrit. 2 - Water-react 1

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

9.3 °F

Flash Point(C)

-12.6 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Isidoro González-Álvaro et al.
Rheumatology (Oxford, England), 54(7), 1200-1209 (2014-12-21)
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Inflammatory bowel diseases, 21(11), 2598-2604 (2015-08-06)
Inflammatory bowel diseases (IBD) are systemic conditions that commonly display extraintestinal manifestations. Inflammatory articular disease (IAD: axial or peripheral) is the most common extraintestinal manifestation. The aim of this study was to evaluate the prevalence and the clinical characteristics associated
Santiago Palacio et al.
International journal of stroke : official journal of the International Stroke Society, 10(5), 686-691 (2013-05-23)
It remains controversial whether dual antiplatelet therapy reduces stroke more than aspirin alone. We aimed to assess the effects of adding clopidogrel to aspirin on the occurrence of stroke and major haemorrhage in patients with vascular disease. Meta-analysis of published
Elin S Gray et al.
Oncotarget, 6(39), 42008-42018 (2015-11-03)
Repeat tumor biopsies to study genomic changes during therapy are difficult, invasive and data are confounded by tumoral heterogeneity. The analysis of circulating tumor DNA (ctDNA) can provide a non-invasive approach to assess prognosis and the genetic evolution of tumors
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