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Sigma-Aldrich

2,5-Dibromothiophene

95%

Synonym(s):

2,5-dibromo-thiophene

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About This Item

Empirical Formula (Hill Notation):
C4H2Br2S
CAS Number:
3141-27-3
Molecular Weight:
241.93
EC Number:
221-547-3
MDL number:
MFCD00005420
UNSPSC Code:
12352100
PubChem Substance ID:
24846807
NACRES:
NA.22

Assay

95%

refractive index

n20/D 1.629 (lit.)

bp

211 °C (lit.)

mp

−6 °C (lit.)

density

2.147 g/mL at 25 °C (lit.)

SMILES string

Brc1ccc(Br)s1

InChI

1S/C4H2Br2S/c5-3-1-2-4(6)7-3/h1-2H

InChI key

KBVDUUXRXJTAJC-UHFFFAOYSA-N

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General description

2,5-Dibromothiophene polymerizes by debromination with magnesium catalyzed by nickel compounds to form poly(2,5- thienylene) .

Application

2,5-Dibromothiophene was used as starting reagent for the synthesis of α,α′-didecylquater-, -quinque- and -sexi-thiophenes. It was used in the preparation of soluble α,ω-diformyl-a-oligothiophenes.

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

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

210.2 °F - closed cup

Flash Point(C)

99 °C - closed cup

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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Synthesis and characterization of 3−hexyl multi−substituted α, ω−diformyl−α−oligothiophenes (n= 3, 6, 8).
Olinga T, et al.
Macromolecular Chemistry and Physics, 198(4), 1091-1107 (1997)
Preparation of thermostable and electric-conducting poly (2, 5-thienylene).
Yamamoto T, et al.
Journal of Polymer Science - Part C: Polymer Letters, 18(1), 9-12 (1980)
Synthesis and thermal behaviour of α, α'-didecyloligothiophenes.
Ponomarenko S and Kirchmeyer S.
Journal of Materials Chemistry, 13(2), 197-202 (2003)
Minami Kato et al.
ChemSusChem, 13(9), 2379-2385 (2020-02-11)
Many types of batteries have been proposed as next-generation energy-storage systems. One candidate is a rocking-chair-type "molecular ion battery" in which a molecular ion, instead of Li+ , works as a charge carrier. Previously, we reported a viologen-type derivative as

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