37067-95-1

Basic information

• Product Name: 2-Iodo-1-methyl-1H-imidazole
• Synonyms: 2-IODO-1-METHYL-1H-IMIDAZOLE;2-IODO-1-METHYLIMIDAZOLE;1H-Imidazole, 2-iodo-1-methyl-
• CAS NO: 37067-95-1
• Molecular Formula: C₄H₅IN₂
• Molecular Weight: 208
• Product Categories: blocks;Imidazoles;Iodides;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Indazoles;New Products for Chemical Synthesis
• Mol File: 37067-95-1.mol

Chemical Properties

• Melting Point: 87 °C
• Boiling Point: 120-122°C 45mm
• Flash Point: 113.1 °C
• Appearance: /
• Density: 2.076 g/cm³
• Vapor Pressure: 0.0103mmHg at 25°C
• Refractive Index: 1.681
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.17±0.25(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 2-Iodo-1-methyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-1-methyl-1H-imidazole(37067-95-1)
• EPA Substance Registry System: 2-Iodo-1-methyl-1H-imidazole(37067-95-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-41-37/38
• Safety Statements: 26-36/37/39-22-39
• WGK Germany: 3
• Hazardous Substances Data: 37067-95-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Iodo-1-methyl-1H-imidazole is used as an intermediate in the synthesis of various pharmaceutical compounds for its potential biological activity and reactivity in chemical reactions. Its imidazole ring structure allows for versatile modifications, making it a valuable building block in drug development.
Used in Chemical Research:
2-Iodo-1-methyl-1H-imidazole is used as a research compound in academic and industrial laboratories for studying the properties and reactions of imidazole derivatives. Its iodo and methyl groups provide opportunities for further functionalization and exploration of new chemical pathways.
Used in Material Science:
2-Iodo-1-methyl-1H-imidazole is used as a component in the development of new materials with specific properties, such as in the synthesis of ionic liquids or as a dopant in organic semiconductors. Its unique structure and reactivity contribute to the creation of materials with tailored characteristics for various applications.

InChI:InChI=1/C4H5IN2/c1-7-3-2-6-4(7)5/h2-3H,1H3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 

Downstream Products

• 111600-87-4 1-methyl-2-(2-phenylethynyl)-1H-imidazole 
• 37570-94-8 1,1'-dimethyl-2,2'-biimidazole 
• 13369-86-3 2-Iodo-1-methyl-4-nitroimidazole 
• 949097-24-9 C₁₄H₁₄N₄ 
• 1351782-57-4 2-(2-bromophenyl)-1-methylimidazole 
• 1346244-13-0 N-(3,5-dimethoxyphenyl)-N-[3-(1-methyl-1H-imidazol-2-yl)prop-2-yn-1-yl]-3-(1-methyl-1H-pyrazol-4-yl)quinoxalin-6-amine 
• 616-47-7 1-methyl-1H-imidazole 
• 1022964-91-5 [2-(1-methyl-1H-imidazol-2-yl)-phenyl]-carbamic acid tert-butyl ester 
• 92506-23-5 2-benzyl-1-methyl-1H-imidazole 
• 910918-23-9 2-(3,5-di-tert-butyl-2-methoxybenzyl)-1-methylimidazole 
• 910918-22-8 2-(2-methoxybenzyl)-1-methylimidazole 
• 3475-07-8 N-methyl-2-phenyl-1H-imidazole 

Relevant articles and documents

Noble Metal Corrosion: Halogen Bonded Iodocarbenium Iodides Dissolve Elemental Gold—Direct Access to Gold–Carbene Complexes

A common method to dissolve elemental gold involves the combination of an oxidant with a Lewis base that coordinates to the gold surface, thus lowering the metal's redox potential. Herein we report the usage of organic iodide salts, which provide both oxidative power and a coordinating ligand, to dissolve gold under formation of organo-gold complexes. The obtained products were identified as AuIII complexes, all featuring Au?C bonds, as shown by X-ray single-crystal analysis, and can be isolated in good yields. Additionally, our method provides direct access to N-heterocyclic carbene (NHC-type) complexes and avoids costly organometallic precursors. The investigated complexes show dynamic behavior in acetonitrile and in the case of the NHC(-type) complexes, the involved species could be identified as a monocarbene [AuI3(carbene)] and biscarbene complex [AuI2(carbene)2]+.

NMR Quantification of Halogen-Bonding Ability to Evaluate Catalyst Activity

Quantification of halogen-bonding abilities is described for a series of benzimidazolium-, imidazolium- and bis(imidazolium) halogen-bond donors (XBDs) using 31P NMR spectroscopy. The measured Δδ(31P) values correlate with calculated activation free energ

Zinc-Ion-Stabilized Charge-Transfer Interactions Drive Self-Complementary or Complementary Molecular Recognition

Here, we show that charge-transfer interactions determine whether donor and acceptor ditopic ligands will associate in a complementary or self-complementary fashion upon metal-ion clipping. Anthracene-based (9,10LD and 1,5LD) and anthraquinone-based (1,5LA) ditopic ligands containing two imidazole side arms as zinc coordination sites were designed. The 9,10LD and 1,5LA systems associated in a complementary fashion (LA/LD/LA) upon clipping by two zinc ions (Zn2+) to form an alternating donor-acceptor assembly [(9,10LD)(1,5LA)2-(Zn2+)2]. However, once the charge-transfer interactions were perturbed by subtle modifications of the imidazole side arms (9,10LD′(S) and 1,5LA′(S)), self-complementary association (LD′/LD′/LD′/LD′ and LA′/LA′/LA′/LA′) between the donor (9,10LD′(S)) and acceptor (1,5LA′(S)) ligands predominantly occurred to form homoassemblies [(9,10LD′(S))4-(Zn2+)2 and (1,5LA′(S))4-(Zn2+)2]. As in the case of a homochiral pair (9,10LD′(S) and 1,5LA′(S)), self-complementary association (narcissistic self-sorting) occurred in the Zn2+ assembly with heterochiral combinations of the donor and acceptor ligands (9,10LD′(S)/1,5LA′(R) and 9,10LD′(S)/1,5LA′(R)/1,5LA′(R)). Narcissistic self-sorting also took place between the positional isomer of the donor ligands (9,10LD and 1,5LD) to form individual homoligand assemblies [(9,10LD)4-(Zn2+)2 and (1,5LD)4-(Zn2+)2]. Conversely, statistical association took place in the Zn2L4 assembly process of an isomorphous pair of the donor and acceptor ligands (1,5LD and 1,5LA).

Dynamic Open Coordination Cage from Nonsymmetrical Imidazole–Pyridine Ditopic Ligands for Turn-On/Off Anion Binding

This work demonstrates a new nonconventional ligand design, imidazole/pyridine-based nonsymmetrical ditopic ligands (1 and 1S), to construct a dynamic open coordination cage from nonsymmetrical building blocks. Upon complex formation with Pd2+ at a 1:4 molar ratio, 1 and 1S initially form mononuclear PdL4 complexes (Pd2+(1)4 and Pd2+(1S)4) without formation of a cage. The PdL4 complexes undergo a stoichiometrically controlled structural transition to Pd2L4 open cages ((Pd2+)2(1)4 and (Pd2+)2(1S)4) capable of anion binding, leading to turn-on anion binding. The structural transitions between the Pd2L4 open cage and the PdL4 complex are reversible. Thus, stoichiometric addition (2 equiv) of free 1S to the (Pd2+)2(1S)4 open cage holding a guest anion ((Pd2+)2(1S)4?G?) enables the structural transition to the Pd2+(1S)4 complex, which does not have a cage and thus causes the release of the guest anion (Pd2+(1S)4+G?).

Palladium(ii) N-heterocyclic allenylidene complexes with extended intercationic Pd?Pd interactions and MMLCT phosphorescence

Extended intercationic Pd?Pd contacts of 3.30 ? in the crystal structure and distinct MMLCT transitions absorbing at 528 nm and emitting beyond 600 nm in solutions have been revealed with cyclometalated Pd(ii) N-heterocyclic allenylidene complexes. The Pd

T -BuONa-mediated direct C-H halogenation of electron-deficient (hetero)arenes

An efficient halogenation of electron-deficient (hetero)arenes is described. The reaction utilizes common t-BuONa as a catalyst (for iodination) or a promoter (for bromination and chlorination), and perfluorobutyl iodide, CBr4 or CCl4 as the readily-available halogenating agents, respectively. The protocol features broad scope, high efficiency, mild conditions and gram scalability. An ionic pathway involving halogen bond formation and halophilic attack is proposed. The utility of the resulting iodinated heteroarenes is demonstrated in visible light-mediated Caryl-Caryl cross-coupling reaction.

Synthesis of Complexes with Protic NH,NR-NHC Ligands by Oxidative Addition of N-Alkyl-2-iodoimidazoles to [M(PPh3)4] (M = Pd, Pt) Complexes

The oxidative addition of N-methyl-2-iodoimidazole (1) or N-benzyl-2-iodoimidazole (2) to complexes [Pd(PPh3)4] or [Pt(PPh3)4] followed by the protonation of the unsubstituted imidazolato ring nitrogen atom yielded complexes trans-[M(NH,NMe-NHC)(PPh3)2I]PF6 (M = Pd: trans-[3]PF6; M = Pt: trans-[4]PF6) and trans-[M(NH,NBz-NHC)(PPh3)2I]PF6 (M = Pd: trans-[5]PF6; M = Pt: trans-[6]PF6) bearing imidazole-derived protic NH,NR-NHC (pNHC) ligands. In the absence of a proton source, the reaction of 1 with [Pd(PPh3)4] yielded the dinuclear dipalladium complex [7] featuring bridging imidazolato ligands metalated at the C2 ring-carbon atom and the N3 ring-nitrogen atom. Palladium complex trans-[3]PF6 undergoes halogen abstraction with AgPF6 to give acetonitrile complex trans-[Pd(NCCH3)(NH,NMe-NHC)(PPh3)2](PF6)2 trans-[8](PF6)2. This complex reacts further with 1,10-phenanthroline (phen), affording complex [Pd(NH,NMe-NHC)(PPh3)(phen)](PF6)2 [9](PF6)2.

Method for preparing halogenated (hetero) aromatic hydrocarbons

The invention relates to a method for preparing halogenated (hetero) aromatic hydrocarbons. The halogenated (hetero) aromatic hydrocarbons are prepared from cheap and easily available perfluorobutyl iodide, carbon tetrabromide and carbon tetrachloride as iodinated, brominated and chlorinated reagents respectively under the action of alkali catalysis (promotion). The method comprises the following steps: firstly, (hetero) aromatic hydrocarbons, a halogenated reagent and an inorganic base are placed in an organic solvent, stirred at room temperature and monitored with TLC until a substrate disappears, and the reaction is stopped; then, a reaction mixed solution is poured into water and extracted, an organic phase is dried, and the organic solvent is removed under reduced pressure; finally, silica-gel column chromatography is performed on a crude product, and a product is obtained. Purification can also be performed by recrystallization. The method has the advantages that the synthetic route is wide in substrate range, raw materials and reagents are cheap and easily available, operation is simple, conditions are mild, yield is high, energy consumption is reduced, the reaction route is safe, gram-grade preparation can be performed and the like.

Zwitterionic-Type Molten Salt Catalyzed Iodination in Water: Synthesis of Iodoimidazoheterocycles

An environmentally benign protocol for the iodination of imidazoheterocycles has been developed through sp2 C-H bond functionalization with molecular iodine in water at room temperature. The reaction is catalyzed by an imidazole-based zwitterio

Homoleptic gold(i) N-heterocyclic allenylidene complexes: Excited-state properties and lyotropic chromonics

A series of phosphorescent Au(i) bis(N-heterocyclic allenylidene) complexes, namely [Au(=C=C=CR1R2)2]+X-, were synthesized and structurally characterized. These organometallic complexes exhibit panchromatic transient absorption upon electronic photo-excitation and can self-organize into lyotropic chromonic mesophases in aqueous solutions.