5-Chloro-1-methylimidazole

Base Information

• Chemical Name: 5-Chloro-1-methylimidazole
• CAS No.: 872-49-1
• Molecular Formula: C4H5ClN2
• Molecular Weight: 116.55
• Hs Code.: 2933290090
• European Community (EC) Number: 212-827-6
• DSSTox Substance ID: DTXSID50236175
• Nikkaji Number: J26.568C
• Wikidata: Q72454071
• Mol file: 872-49-1.mol

Synonyms:5-Chloro-1-methylimidazole;872-49-1;5-Chloro-1-methyl-1H-imidazole;1-Methyl-5-chloroimidazole;1H-Imidazole, 5-chloro-1-methyl-;C4H5ClN2;EINECS 212-827-6;MFCD00014505;5-Chloro-1-Methylimidazole,98%;SCHEMBL1132866;DTXSID50236175;5-Chloro-1-methylimidazole, 98%;5-Chloro-1-methyl-1H-imidazole #;STK505483;AKOS001284087;AM804452;AS-14596;SY041529;BB 0254715;C2317;CS-0151157;FT-0620217;EN300-24053;W10455;A842051;AA-516/30012007;Z168874650

Chemical Property of 5-Chloro-1-methylimidazole

Chemical Property:

• Appearance/Colour: pale yellow oil
• Vapor Pressure: 0.33mmHg at 25°C
• Melting Point: 82-85 °C(11 mmHg)
• Refractive Index: n20/D 1.511(lit.)
• Boiling Point: 207.1 °C at 760 mmHg
• PKA: 5.31±0.10(Predicted)
• Flash Point: 96.1 °C
• PSA: 17.82000
• Density: 1.26 g/cm³
• LogP: 1.07350
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in chloroform and insoluble in water
• Water Solubility.: insoluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 116.0141259
• Heavy Atom Count: 7
• Complexity: 66.7

Purity/Quality:

99% ^*data from raw suppliers

5-Chloro-1-methylimidazole-13C4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C=NC=C1Cl
• Uses: 5-Chloro-1-methylimidazole is a labelled useful synthetic intermediate.

Technology Process of 5-Chloro-1-methylimidazole

There total 7 articles about 5-Chloro-1-methylimidazole 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: 96.0%

1-methyl-1H-imidazole (616-47-7) → N-methyl-5-chloroimidazole (872-49-1)

Guidance literature:

With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; In acetonitrile; at 0 ℃; for 0.25h; Green chemistry;

DOI:10.1016/j.tetlet.2020.152689

Reference yield: 95.0%

N,N'-dimethyloxamide (615-35-0) → N-methyl-5-chloroimidazole (872-49-1)

Guidance literature:

With phosphorus pentachloride; trichlorophosphate; 1.) 100 deg C, 45min; 2.) 92 deg C, 75min;

Reference yield: 69.0%

4-chloro-1H-imidazole (15965-31-8) + methyl iodide (74-88-4) → N-methyl-5-chloroimidazole (872-49-1)

Guidance literature:

4-chloro-1H-imidazole; With methylmagnesium 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

upstream raw materials:

dimethyloxamide

N,N'-dimethyloxamide

N-formylglycine methylamide

1-allyl-4-chloro-3-methyl-imidazolium; bromide

Downstream raw materials:

Br^(1-)*C₂₀H₁₈ClN₂O⁽¹⁺⁾

Br^(1-)*C₂₀H₁₆Cl₃N₂O⁽¹⁺⁾

Br^(1-)*C₂₂H₂₂ClN₂O₃⁽¹⁺⁾

5-chloro-1-methyl-2-(4-trifluoromethylphenyl)imidazole

Refernces

• 1、 Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh. "Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)". supporting information. . Retrieved 2021/01/04.
• 2、 Chen, Shuai,Graceffa, Russell F.,Boezio, Alessandro A.. "Direct, Regioselective N-Alkylation of 1,3-Azoles". supporting information. p. 16 - 19. Retrieved 2016/01/15.