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673099

Sigma-Aldrich

Biphenyl-4,4′-dithiol

95%

Synonym(s):

4,4′-Dimercaptobiphenyl, BDT, BPDT

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About This Item

Linear Formula:
HSC6H4C6H4SH
CAS Number:
6954-27-4
Molecular Weight:
218.34
EC Number:
230-136-8
MDL number:
MFCD00046826
UNSPSC Code:
12352103
PubChem Substance ID:
24885141
NACRES:
NA.23

Assay

95%

form

solid

mp

165-174 °C

storage temp.

−20°C

SMILES string

Sc1ccc(cc1)-c2ccc(S)cc2

InChI

1S/C12H10S2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8,13-14H

InChI key

VRPKUXAKHIINGG-UHFFFAOYSA-N

Related Categories

General description

Biphenyl-4,4′-dithiol (BPDT) is an aryl dithiol that is prepared by taking a mixture of stannous chloride dihydrate and glacial acetic acid with anhydrous hydrogen chloride. It forms a self-assembled monolayer on a variety of surfaces by attaching one thiol group to the surface while the other can create nucleation sites for other functional groups.

Application

BPDT can be used to functionalize iron nanoparticles (NPs) with the gold shell (Fe−Au) on polyethylene substrate. It can also be coated on the p-doped gallium arsenic (GaAs) substrate for a variety of semiconductor applications.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H413

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Journal of the American Chemical Society, 73(3), 1097-1099 (1951)
Michael Riskin et al.
Journal of the American Chemical Society, 128(4), 1253-1260 (2006-01-26)
The electroswitchable and the biocatalytic/electrochemical switchable interfacial properties of a Ag(+)-biphenyldithiol (BPDT) monolayer associated with a Au surface are described. Upon the application of a potential corresponding to -0.2 V the Ag(+)-BPDT is reduced to the Ag(0)-BPDT interface, and silver
Niels W L Van Steenkiste et al.
Science advances, 5(7), eaaw4337-eaaw4337 (2019-07-23)
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