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Sigma-Aldrich

2-Bromothiophene

98%

Synonym(s):

2-Thienyl bromide

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10 G
$42.90
50 G
$74.70
250 G
$58.00

About This Item

Empirical Formula (Hill Notation):
C4H3BrS
CAS Number:
1003-09-4
Molecular Weight:
163.04
Beilstein/REAXYS Number:
104663
EC Number:
213-699-4
MDL number:
MFCD00005417
UNSPSC Code:
12352100
PubChem Substance ID:
24847601
NACRES:
NA.22

$42.90

Available to ship onApril 22, 2025Details

Request a Bulk Order

Quality Level

100

assay

98%

form

liquid

refractive index

n20/D 1.586 (lit.)

bp

149-151 °C (lit.)

density

1.684 g/mL at 25 °C (lit.)

functional group

bromo

storage temp.

2-8°C

SMILES string

Brc1cccs1

InChI

1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H

InChI key

TUCRZHGAIRVWTI-UHFFFAOYSA-N

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General description

2-Bromothiophene undergoes metalation-alkylation reaction with various electrophiles to form various 5-alkylated 2-bromo products[1]. It undergoes coupling with 4-bromo allyl phenyl ether to form allyl phenyl thiophene ether, which is a novel potential dielectric material for organic thin film transistors[2].

Application

2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium perchlorate by cyclic voltammetry and controlled-potential electrolysis[3].

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Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

125.6 °F - closed cup

flash_point_c

52 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBL1062
STBK7747
STBK6692
STBK3748
STBK2886

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Novel self assembled monolayers of allyl phenyl thiophene ether as potential dielectric material for organic thin film transistors.
Sathyapalan A, et al
Thin Solid Films, 516(16), 5645-5648 (2008)
R A Ingle et al.
The Journal of chemical physics, 147(1), 013914-013914 (2017-07-10)
The ultraviolet photochemistry of 2-bromothiophene (C
Synlett, 974-974 (2007)
First example of base-promoted tandem alkylation-bromination of 2-bromothiophene via halogen dance process: a remarkable temperature effect.
Peyron C, et al.
Tetrahedron Letters, 46(19), 3315-3318 (2005)
Mohammad S. Mubarak et al.
The Journal of organic chemistry, 61(23), 8074-8078 (1996-11-15)
Cyclic voltammetry and controlled-potential electrolysis have been employed to probe the electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium perchlorate. Reduction of 2-bromo-, 3-bromo-, 2-chloro-, 3-chloro-, and 2-iodothiophene gives rise to a
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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