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901464

Sigma-Aldrich

2,2′-Bi-1,3,2-dioxaborinane

greener alternative

≥95%

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Synonym(s):
B2(pro)2, Propanediol diboron
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
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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

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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 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

related product

Product No.
Description
Pricing

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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.

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Morken Group – Professor Product Portal

Chiral organoboronic esters are well known as versatile intermediates for chemical synthesis. Not only are these compounds stable under a variety of reaction conditions, they are generally non-toxic and can be transformed with minimal generation of hazardous waste.

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