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%,99%, ^*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

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

4-chloro-2-(thiophene-2-carbonyl)-benzoic acid

5-chloro-2-(thiophene-2-carbonyl)-benzoic acid

Refernces

• 1、 Wu, Jiazun,Li, Xiangchun,Liu, Xiaodong,Wu, Shuanghong,Lai, Wen-Yong,Zheng, Yonghao. "Effects of conjugated bridges on the photovoltaic properties of: Ortho -functionalized perylene diimides for non-fullerene polymer solar cells". . p. 13171 - 13178. Retrieved 2018.
• 2、 Deitmann, Eva,G?ssl, Lars,Hofmann, Christian,L?b, Patrick,Menges-Flanagan, Gabriele. "Scalable Continuous Synthesis of Grignard Reagents from in Situ-Activated Magnesium Metal". . p. 315 - 321. Retrieved 2020/03/10.