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106550

Sigma-Aldrich

meso-1,2-Dibromo-1,2-diphenylethane

≥97%

Synonym(s):

Stilbene dibromide

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About This Item

Linear Formula:
C6H5CH(Br)CH(Br)C6H5
CAS Number:
Molecular Weight:
340.05
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥97%

form

solid

mp

241 °C (dec.) (lit.)

functional group

bromo
phenyl

SMILES string

Br[C@H]([C@H](Br)c1ccccc1)c2ccccc2

InChI

1S/C14H12Br2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H/t13-,14+

InChI key

GKESIQQTGWVOLH-OKILXGFUSA-N

General description

meso-1,2-Dibromo-1,2-diphenylethane undergoes electrochemical dehalogenation in acetonitrile. It is reduced by electrogenerated C60−3.

Application

meso-1,2-Dibromo-1,2-diphenylethane(meso-SBr2) was used to study the reaction of ± and meso-SBr2 with 9-substituted fluorenide ions in dimethyl sulfoxide.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  4. Is Stilbene dibromide, Product 106550, optically active?

    Generally, chiral molecules are optically active, rotating polarized light. Meso compounds, such as 106550, are unique in that there are chiral carbons in the molecule yet they are not optically active. meso-1,2-Dibromo-1,2-diphenylethane has chiral carbons that are virtually identical but the arrangement of the groups on this carbon are different; the result of these opposing effects is a net optical rotation of zero.

  5. In what solvents is Stilbene dibromide, Product 106550, soluble?

    Sigma-Aldrich does not currently test this product for solubility in a particular solvent. However, our quality control does solubilize this product with acetonitrile (with sonication) for analysis by HPLC at a concentration of 0.5mg/mL.

  6. Where can I find product similar to meso-1,2-Dibromo-1,2-diphenylethane offered by Sigma-Aldrich?

    The Sigma-Aldrich website provides many resources for locating products with similar structural characteristics. At the bottom of the product information page for product 106550, there are links to "Related Categories". These links including listings of Sigma-Aldrich products that fall in the same category as meso-1,2-Dibromo-1,2-diphenylethane. Alternatively, Sigma-Aldrich offers an online catalog that provides organized listings of products useful for chemical synthesis, grouped by similar characteristics.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

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Reduction of Vicinal Dihalides. I. The Electrochemical Reduction of meso and (?)-1, 2-Dibromo-1, 2-diphenylethane.
Fawell P, et al.
Australian Journal of Chemistry, 43(8), 1421-1430 (1990)
Electro-organic chemistry of fullerenes. Part 1. Indirect cathodic reduction of vic-dihalides and perfluoroalkyl halides using C60 as mediator. Cyclic voltammetric study and preparative-scale electrolysis.
Fuchigami T, et al.
Journal of Electroanalytical Chemistry, 411(1), 115-119 (1996)
Debromination of meso-and (?)-1, 2-Dibromo-1, 2-diphenylethane by 9-Substituted Fluorenide Ions: Correlation between Stereochemical Results and Redox Potentials.
Lund T, et al.
Acta Chemica Scandinavica, 47, 877-877 (1993)

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