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790796

Sigma-Aldrich

Zinc benzylsulfinate

Synonym(s):

Zinc benzylsulfinate, Baran BNS Reagent

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About This Item

Empirical Formula (Hill Notation):
C14H14O4S2Zn
CAS Number:
21799-75-7
Molecular Weight:
375.78
UNSPSC Code:
12352002
PubChem Substance ID:
329768240
NACRES:
NA.22

form

solid

reaction suitability

reaction type: Alkylations
reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation
reagent type: diversification reagent

mp

56 °C (Decomposition)

storage temp.

2-8°C

SMILES string

O=S(O[Zn]OS(CC1=CC=CC=C1)=O)CC2=CC=CC=C2

InChI

1S/2C7H8O2S.Zn/c2*8-10(9)6-7-4-2-1-3-5-7;/h2*1-5H,6H2,(H,8,9);/q;;+2/p-2

InChI key

AHSIXHPQMGLVIG-UHFFFAOYSA-L

Application

Zinc benzylsulfinate (BNS) is part of a zinc sulfinate toolbox developed by Phil Baran for the simple and rapid diversification of heterocycles.


Practical and Innate Carbon-Hydrogen Functionalization of Heterocycles

Learn More at the Professor and Product Portal of Professor Phil S. Baran.

Other Notes

may contain up to 1 mole eq ZnCl2

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3756
MKCQ5697
MKCG3302
MKBV1021V
MKBQ7984V

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Fionn O'Hara et al.
Journal of the American Chemical Society, 135(32), 12122-12134 (2013-07-19)
Radical addition processes can be ideally suited for the direct functionalization of heteroaromatic bases, yet these processes are only sparsely used due to the perception of poor or unreliable control of regiochemistry. A systematic investigation of factors affecting the regiochemistry
Yuta Fujiwara et al.
Nature, 492(7427), 95-99 (2012-12-04)
Nitrogen-rich heterocyclic compounds have had a profound effect on human health because these chemical motifs are found in a large number of drugs used to combat a broad range of diseases and pathophysiological conditions. Advances in transition-metal-mediated cross-coupling have simplified

Articles

Baran Diversinates™

The synthesis of heteroaromatic and aromatic compounds is at the heart of the chemical industry. The ever-growing demand for new chemical entities, coupled with dwindling resources and time constraints allotted to any given research project, a rapid way to diversify (hetero)aromatic scaffolds is needed.

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