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550442

Sigma-Aldrich

2-Thienylmagnesium bromide solution

1.0 M in THF

Synonym(s):

(Thiophen-2-yl)magnesium bromide, Bromo-2-thienylmagnesium

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About This Item

Empirical Formula (Hill Notation):
C4H3BrMgS
CAS Number:
5713-61-1
Molecular Weight:
187.34
MDL number:
MFCD03094046
UNSPSC Code:
12352103
PubChem Substance ID:
24879115
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

bp

65 °C

density

1.011 g/mL at 25 °C

SMILES string

Br[Mg]c1cccs1

InChI

1S/C4H3S.BrH.Mg/c1-2-4-5-3-1;;/h1-3H;1H;/q;;+1/p-1

InChI key

GSHPYJFNTAMRJF-UHFFFAOYSA-M

Related Categories

Application

2-Thienylmagnesium bromide is a Grignard reagent that can be used as a reactant to synthesize:
  • 1-(2-thienyl)-carbinols by condensation reaction with aldehydes. Carbinols are further dehydrated to form 2-thienyl olefins.
  • Thiophene-functionalized polystyrene macromonomer (ThPStM), which is employed as a key intermediate to synthesize polystyrene-graft-polythiophene (PSt-g-PTh) via a combination of atom transfer radical polymerization (ATRP) and Grignard reaction.
  • Thienylene oligomers, which are used as conducting polymers and as potential OLEDs.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-6.0 °F - closed cup

flash_point_c

-21.1 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM6662
SHBF8386V
SHBD1420V
43196TM
09304CJ

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A convenient synthesis of 2, 5-thienylene oligomers; some of their spectroscopic and electrochemical properties
Van Pham C, et al.
Phosphorus, Sulfur, and Silicon and the Related Elements, 46(3-4), 153-168 (1989)
Synthesis and characterization of 9, 9-dialkylfluorene capped benzo [c] thiophene/benzo [c] selenophene analogs as potential OLEDs
Mohanakrishnan AK, et al.
Tetrahedron Letters, 49(32), 4792-4795 (2008)
Condensations of aldehydes with 2-thienyllithium, 2-thienylsodium and 2-thienylmagnesium bromide
Van ZG, et al.
Journal of the American Chemical Society, 78(9), 1955-1958 (1956)
Atom transfer radical polymerization of MMA with a macromolecular ligand in a fluorinated solvent and in supercritical carbon dioxide.
Grignard B, et al.
European Polymer Journal, 44(3), 861-871 (2008)

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