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901464

Sigma-Aldrich

2,2′-Bi-1,3,2-dioxaborinane

greener alternative

≥95%

Synonym(s):

B2(pro)2, Propanediol diboron

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About This Item

Empirical Formula (Hill Notation):
C6H12B2O4
CAS Number:
13826-25-0
Molecular Weight:
169.78
MDL number:
MFCD08460171
UNSPSC Code:
12352200
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder or crystals

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

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Greener Alternative Product

mp

156 °C

greener alternative category

Aligned,

storage temp.

−20°C

InChI

1S/C6H12B2O4/c1-3-9-7(10-4-1)8-11-5-2-6-12-8/h1-6H2

InChI key

FOGDFVUQHQEIPV-UHFFFAOYSA-N

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 has been enhanced to increase catalytic efficiency. Click here for more information.

Application

As reported by the laboratory of James Morken, B2(pro)2 is an effective reagent for enantioselective diboration of alkenes when used in conjunction with the carbohydrate-derived catalysts TBS-DHG (901235) or DHR (901237). Useful for synthesis of other boron-containing molecules.

Other Notes

Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

901464-BULK:
901464-500MG:
901464-VAR:

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TBS-DHG Catalyst ≥95%

Sigma-Aldrich

901235

TBS-DHG Catalyst

Lu Yan et al.
Journal of the American Chemical Society, 140(10), 3663-3673 (2018-02-15)
A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

Articles

Carbohydrate-Catalyzed Enantioselective Alkene Diboration

Enantioselective alkene diboration is a valuable strategy for transforming unsaturated hydrocarbons into useful chiral building blocks.

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