1,3-Dimethylimidazolium iodide

Base Information

• Chemical Name: 1,3-Dimethylimidazolium iodide
• CAS No.: 4333-62-4
• Molecular Formula: C5H9IN2
• Molecular Weight: 224.044
• Hs Code.: 29332900
• European Community (EC) Number: 801-371-9
• NSC Number: 114468
• DSSTox Substance ID: DTXSID40962991
• Wikidata: Q27131032
• Metabolomics Workbench ID: 61590
• ChEMBL ID: CHEMBL1214173
• Mol file: 4333-62-4.mol

Synonyms:1,3-Dimethylimidazolium iodide;4333-62-4;1,3-dimethyl-1H-imidazol-3-ium iodide;1,3-dimethylimidazol-1-ium iodide;1-Methylimidazole methiodide;1,3-dimethylimidazol-1-ium;iodide;1,3-Dimethyl-3-imidazolium Iodide;NSC 114468;CHEBI:61324;MFCD00159685;IMIDAZOLIUM, 1,3-DIMETHYL-, IODIDE;1,3-Dimethylimidazoliumiodide;C5H9IN2;SCHEMBL359425;C5H9N2.I;1,3-dimethyl imidazolium iodide;CHEMBL1214173;DTXSID40962991;C5-H9-N2.I;NSC114468;AKOS015964830;1,3-dimethyl-1H-imidazol-3-iumiodide;NSC-114468;SB21851;AS-19711;LS-79775;SY039191;A6988;CS-0038445;D4654;FT-0600272;1H-Imidazolium, 1,3-dimethyl-, iodide (9CI);Q27131032

Chemical Property of 1,3-Dimethylimidazolium iodide

Chemical Property:

• Melting Point: 84.0 to 89.0 °C
• PSA: 8.81000
• LogP: -3.14640
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 223.98105
• Heavy Atom Count: 8
• Complexity: 55.1

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dimethylimidazolium Iodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C=C[N+](=C1)C.[I-]

Technology Process of 1,3-Dimethylimidazolium iodide

There total 28 articles about 1,3-Dimethylimidazolium iodide 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: 100.0%

1-methyl-1H-imidazole (616-47-7) + methyl iodide (74-88-4) → 1,3-dimethylimidazolim iodide (4333-62-4)

Guidance literature:

In dichloromethane; for 1h;

DOI:10.1021/acs.joc.5b01682

Reference yield: 100.0%

(1,3-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene)diiodo(pyridine)palladium → 1,3-dimethylimidazolim iodide (4333-62-4)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 140 ℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1021/acs.organomet.8b00124

Reference yield: 96.6%

2-(Hydroxy-diphenyl-methyl)-1,3-dimethyl-3H-imidazol-1-ium; iodide (111931-07-8) → benzophenone (119-61-9) + 1,3-dimethylimidazolim iodide (4333-62-4)

Guidance literature:

With potassium carbonate; In benzene; at 60 ℃; for 2h; Product distribution; further reagent; var. time;

upstream raw materials:

1H-imidazole

methyl iodide

1-methyl-1H-imidazole

2-(1-hydroxy-1-phenyl-1-pentyl)-1-methyl-1H-imidazole

Downstream raw materials:

1,3-dimethyl-1H-imidazol-3-ium hydrogen carbonate

N,N'-dimethylimidazolium-2-carboxylate

(1,3-dimethyl-1H-imidazol-3-ium-2-yl)(phenyl)dihydroborate

(1,3-dimethyl-1H-imidazol-3-ium-2-yl)(4-methoxyphenyl)dihydroborate

Refernces

• 1、 Denning, Derek M.,Thum, Matthew D.,Falvey, Daniel E.. "Photochemical Reduction of CO2 Using 1,3-Dimethylimidazolylidene". . p. 4152 - 4155. Retrieved 2015.
• 2、 Sarmiento, Gabriela P.,Zelcer, Andrés,Espinosa, Mariela S.,Babay, Paola A.,Mirenda, Martin. "Photochemistry of imidazolium cations. Water addition to methylimidazolium ring induced by UV radiation in aqueous solution". . p. 155 - 163. Retrieved 2016.
• 3、 Dzyuba,Bartsch. "New room-temperature ionic liquids with C2-symmetrical imidazolium cations". . p. 1466 - 1467. Retrieved 2001.
• 4、 Xie, Han Jin,Gélinas, Bruno,Rochefort, Dominic. "Electrochemical and physicochemical properties of redox ionic liquids using electroactive anions: Influence of alkylimidazolium chain length". . p. 283 - 289. Retrieved 2016.
• 5、 Gothe, Yvonne,Marzo, Tiziano,Messori, Luigi,Metzler-Nolte, Nils. "Iridium(I) Compounds as Prospective Anticancer Agents: Solution Chemistry, Antiproliferative Profiles and Protein Interactions for a Series of Iridium(I) N-Heterocyclic Carbene Complexes". . p. 12487 - 12494. Retrieved 2016.
• 6、 Oertel, Anna Magdalena,Ritleng, Vincent,Burr, Loic,Chetcuti, Michael J.. "Synthesis and structural characterization of half-sandwich nickel complexes bearing two different n-heterocyclic carbene ligands". . p. 6685 - 6691. Retrieved 2011.
• 7、 Bolotin, Dmitrii S.,Il'in, Mikhail V.,Novikov, Alexander S.,Suslonov, Vitalii V.,Sysoeva, Alexandra A.. "Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study". supporting information. p. 7611 - 7620. Retrieved 2021/09/22.
• 8、 Mandal, Tanmoy,Yadav, Sudha,Choudhury, Joyanta. "Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes". . . Retrieved 2021/09/06.