2-Thienylmagnesium bromide

Base Information

• Chemical Name: 2-Thienylmagnesium bromide
• CAS No.: 5713-61-1
• Molecular Formula: C4H3BrMgS
• Molecular Weight: 187.343
• Hs Code.: 29349990
• European Community (EC) Number: 692-749-0
• Mol file: 5713-61-1.mol

Synonyms:2-thienylmagnesium bromide;5713-61-1;Bromo-2-thienylmagnesium;2-thienyl magnesium bromide;thiophen-2-ylmagnesium bromide;magnesium;2H-thiophen-2-ide;bromide;MFCD03094046;Thienylmagnesiumbromide;thienylmagnesium bromide;thienyl magnesium bromide;SCHEMBL72771;bromo(thiophen-2-yl)magnesium;thiphen-2-yl magnesium bromide;thiophen-2-yl magnesium bromide;thiophen-2-yl-magnesium bromide;thiophene-2-yl magnesium bromide;thiophene-2-yl-magnesium bromide;GSHPYJFNTAMRJF-UHFFFAOYSA-M;2-Thienylmagnesium bromide, 1.0 M in THF;2-Thienylmagnesium bromide, 1.0 M in 2-MeTHF

Chemical Property of 2-Thienylmagnesium bromide

Chemical Property:

• Vapor Pressure: 81.7mmHg at 25°C
• Boiling Point: 65 °C
• Flash Point: −6 °F
• PSA: 28.24000
• Density: 1.011 g/mL at 25 °C
• LogP: 2.39390
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 185.89893
• Heavy Atom Count: 7
• Complexity: 79.8

Purity/Quality:

98% ^*data from raw suppliers

2-Thienylmagnesium bromide solution 1.0 M in THF ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,C,Xn
• Statements: 11-14-19-22-34-40-36/37
• Safety Statements: 16-26-36/37/39-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CS[C-]=C1.[Mg+2].[Br-]
• Uses: 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.

Technology Process of 2-Thienylmagnesium bromide

There total 12 articles about 2-Thienylmagnesium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2-bromothiophene (1003-09-4) → thiophen-2-yl magnesium bromide (5713-61-1)

Guidance literature:

With magnesium; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere; Flow reactor;

DOI:10.1021/acs.oprd.9b00493

Reference yield: 86.0%

2-bromothiophene (1003-09-4) + magnesium (7439-95-4) → thiophen-2-yl magnesium bromide (5713-61-1)

Guidance literature:

In tetrahydrofuran; at 66 ℃; Time; Inert atmosphere; Heating;

DOI:10.1021/op700080t

Reference yield:

2-bromothiophene (1003-09-4) + 1-[1-(3-hydroxymethyl-piperidino)-cyclohexan-1-yl]-carbonitrile (131774-16-8) → thiophen-2-yl magnesium bromide (5713-61-1) + N-[1-(thien-2-yl)-cyclohexan-1-yl]-3-hydroxymethyl-piperidine

Guidance literature:

With magnesium;

upstream raw materials:

thiophene

2-thienyl lithium

2-bromothiophene

oxothien-2-yl-acetic acid 1-azabicyclo[2.2.2]oct-4-yl ester

Downstream raw materials:

2-thiophenethanol

2-hydroxy-2,2-di(thiophen-2-yl)acetic acid

Phenyl-[2]pyridyl-[2]thienyl-methanol

3-(piperidin-1-yl)-1-(thiophen-2-yl)propan-1-one

Refernces

Extensively Conjugated Tetrathiafulvalene (TTF) ?-Electron Donors with Oligothiophenes Spacer Groups

10.1039/c39930000689

This research focuses on the development of new n-electron donors by combining the tetrathiafulvalene (TTF) system with conjugated backbones of substituted terthienyls to improve control of charge transport and superconducting properties of the corresponding cation radical salts (CRSs). The study aims to increase material dimensionality by modifying the spatial extension of the n-donor and intermolecular interstack bonding. The researchers synthesized extended π-electron donors of the TTF series containing substituted terthienyl spacers using a five-step synthetic route. Key chemicals used include 3-octyl and 3-(3,6-dioxaheptyl)thiophene, bromine, 2-thienylmagnesium bromide, N-methylformanilide, acetic anhydride, and phosphonic acid. The study found that substitution of the conjugated spacer significantly affects the solubility, electronic absorption spectrum, and electrochemical behavior of the donor molecules. For example, the introduction of methyl groups increases solubility, while longer alkyl or oxyalkyl substituents cause red shifts in the absorption spectrum. The terthienyl spacer also leads to a marked decrease in oxidation potentials and a reduction in on-site coulombic repulsion between positive charges in the dication state. The research concludes that these new structures can be considered as first examples of oligothiophenes derivatized by a TTF system, and further work is needed to clarify the mechanisms behind the observed spectral changes and to explore the electrical properties of the conducting adducts obtained by iodine doping.