95184-07-9

Basic information

• Product Name: 3-METHYL-2-THIENYLMAGNESIUM BROMIDE
• Synonyms: 3-METHYL-2-THIENYLMAGNESIUM BROMIDE, 0.5M SOLUTION IN TETRAHYDROFURAN;3-methyl-2-thienylmagnesium bromide solution;3-Methyl-2-thienylmagnesium bromide solution 0.5 in THF;3-Methyl-2-thienylmagnesium bromide, 0.5M solution in THF, AcroSeal;3-Methyl-2-thienylMagnesiuM broMide, 0.5M solution in THF, J&KSeal;3-METHYL-2-THIENYLMAGNESIUM BROMIDE;3-Methyl-2-thienylmagnesium bromide solution 0.5M in THF
• CAS NO: 95184-07-9
• Molecular Formula: C₅H₅BrMgS
• Molecular Weight: 201.37
• Product Categories: Grignard Reagents;Heteroaryl;Organometallic Reagents
• Mol File: 95184-07-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 65 °C
• Flash Point: 1 °F
• Appearance: Clear yellow to brown/Solution
• Density: 0.951 g/mL at 25 °C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-METHYL-2-THIENYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-2-THIENYLMAGNESIUM BROMIDE(95184-07-9)
• EPA Substance Registry System: 3-METHYL-2-THIENYLMAGNESIUM BROMIDE(95184-07-9)

Safety Data

• Hazard Codes: F,C,F+,Xn
• Statements: 11-14-19-22-34-40-12-36/37
• Safety Statements: 16-23-26-36/37/39-45-36/37
• RIDADR: UN 2924 3/PG 2
• Hazardous Substances Data: 95184-07-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H5S.BrH.Mg/c1-5-2-3-6-4-5;;/h2-3H,1H3;1H;/q;;+1/p-1/rC5H5BrMgS/c1-4-2-3-8-5(4)7-6/h2-3H,1H3

Upstream product

• 14282-76-9 2-bromo-3-methylthiophene 

Downstream Products

• 99727-96-5 2-allyl-3-methylthiophene 
• 95184-17-1 3-methyl-2-(2-methyl-1,3-diphenylcyclopropen-3-yl)thiophene 
• 95184-10-4 3-methyl-2-(3-methyl-1,2-diphenylcyclopropen-3-yl)thiophene 
• 157925-24-1 4-chloro-β-methyl-butyrothienone 
• 81294-15-7 3,3”-dimethyl-2,2’:5’,2”-terthiophene 

Relevant articles and documents

The Synthesis of Novel GABA Uptake Inhibitors. Part 2. Synthesis of 5-Hydroxytiagabine, a Human Metabolite of the GABA Reuptake Inhibitor Tiagabine

(R)-1-(4-(2,5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl)butyl)-3-piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2-bromo-3-methylthiophene 3.Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane.An alternative approach involving acylation of 2-lithio-3-methylthiophene 17a was found less satisfying.A metalloporphyrin assisted hydroxylation of tiagabine 1 also yielded the target metabolite.The structure of 5-hydroxytiagabine was confirmed by NMR-data including COSY, ROESY, HMQC and HMBC experiments.