5-Bromo-1-methyl-1H-imidazole

Base Information

• Chemical Name: 5-Bromo-1-methyl-1H-imidazole
• CAS No.: 1003-21-0
• Molecular Formula: C4H5BrN2
• Molecular Weight: 161.001
• Hs Code.: 29332900
• European Community (EC) Number: 629-338-2
• DSSTox Substance ID: DTXSID60363926
• Nikkaji Number: J465.886H
• Wikidata: Q72447166
• Mol file: 1003-21-0.mol

Synonyms:5-Bromo-1-methyl-1H-imidazole;1003-21-0;5-Bromo-1-methylimidazole;1H-Imidazole, 5-bromo-1-methyl-;5-bromo-1-methyl imidazole;MFCD01632218;5-bromo-1-methyl-imidazole;5-bromo-N-methyl-imidazole;SCHEMBL308102;1-Methyl-5-bromo-1H-imidazole;AMY3032;DTXSID60363926;BBL101461;CL2235;STL555257;AKOS005259131;AB09509;CS-W001220;PS-3312;5-Bromo-1-methyl-1H-imidazole, 97%;SY016736;FT-0657370;EN300-93712;A18006;J-650275

Chemical Property of 5-Bromo-1-methyl-1H-imidazole

Chemical Property:

• Appearance/Colour: White to tan crystalline solid
• Vapor Pressure: 0.0106mmHg at 25°C
• Melting Point: 40-44 °C(lit.)
• Refractive Index: 1.606
• Boiling Point: 271.725 °C at 760 mmHg
• PKA: 5.25±0.10(Predicted)
• Flash Point: 118.135 °C
• PSA: 17.82000
• Density: 1.693 g/cm³
• LogP: 1.18260
• Storage Temp.: Keep Cold
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 159.96361
• Heavy Atom Count: 7
• Complexity: 66.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Bromo-1-methyl-1H-imidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C=NC=C1Br

Technology Process of 5-Bromo-1-methyl-1H-imidazole

There total 11 articles about 5-Bromo-1-methyl-1H-imidazole 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: 69.0%

4-bromo-1 H-imidazole (2302-25-2) + methyl iodide (74-88-4) → 5-bromo-N-methylimidazole (1003-21-0)

Guidance literature:

4-bromo-1 H-imidazole; With 2,2,6,6-tetramethylpiperidinylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 70 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02994

Reference yield: 51.0%

4-bromo-1 H-imidazole (2302-25-2) + methyl iodide (74-88-4) → 4-bromo-1-methyl-1H-imidazole (25676-75-9) + 5-bromo-N-methylimidazole (1003-21-0)

Guidance literature:

In methanol; at -25 ℃; for 120h;

Reference yield: 16.0%

1-methyl-1H-imidazole (616-47-7) → 5-bromo-N-methylimidazole (1003-21-0) + 4,5-dibromo-1-methyl-1H-imidazole (1003-50-5)

Guidance literature:

With N-Bromosuccinimide; In chloroform; for 2h; Heating;

upstream raw materials:

4-bromo-1 H-imidazole

dimethyl sulfate

4-bromo-1,3-dimethyl-1H-imidazolium iodide

1-methyl-1H-imidazole

Downstream raw materials:

(5-bromo-1-methyl-1H-imidazol-2-yl)methanol

C₂₃H₂₁N₃O₃

(R,S)-6-[(4-chlorophenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-(3-hydroxy-3-methylbutyn-1-yl)-phenyl)-1-methyl-1H-quinolin-2-one

1-methyl-5-(4-methoxyphenyl)-1H-imidazole

Refernces

• 1、 Bellina, Fabio,Lessi, Marco,Marianetti, Giulia,Panattoni, Alessandro. "Highly regioselective C-5 alkynylation of imidazoles by one-pot sequential bromination and Sonogashira cross coupling". supporting information. p. 3855 - 3857. Retrieved 2015/06/08.
• 2、 Ohba,Mukaihira,Fujii. "Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines". . p. 1784 - 1790. Retrieved 2007/10/02.