1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide
- Product Name
- 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide
- CAS No.
- 7181-87-5
- Chemical Name
- 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide
- Synonyms
- 1,3-dimethylbenzoimidazole;1,3-Dimethylbenzimidazolium iodide;N,N'-Dimethylbenzimidazolium iodide;1,3-Dimethyl-1H-benzimidazolium iodide;1,3-Dimethyl-1H-benzimidazol-3-ium iodide;1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide;1,3-Dimethyl-1H-benzimidazolium iodide;5-bromo-1,3-dimethyl-1H-benzo[d]imidazol-3-ium
- CBNumber
- CB52523885
- Molecular Formula
- C9H11IN2
- Formula Weight
- 274
- MOL File
- 7181-87-5.mol
1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide Property
- Melting point:
- 137-142°C
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- form
- solid
- Appearance
- Off-white to light brown Solid
- InChI
- InChI=1S/C9H11N2.HI/c1-10-7-11(2)9-6-4-3-5-8(9)10;/h3-7H,1-2H3;1H/q+1;/p-1
- InChIKey
- RQGURHMTNSNBQX-UHFFFAOYSA-M
- SMILES
- C1=[N+](C)C2=CC=CC=C2N1C.[I-]
Safety
- WGK Germany
- 2
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- 708593
- Product name
- 1,3-Dimethyl-1H-benzimidazolium iodide
- Packaging
- 250mg
- Price
- $110
- Updated
- 2023/06/20
- Product number
- 708593
- Product name
- 1,3-Dimethyl-1H-benzimidazolium iodide
- Packaging
- 1g
- Price
- $274
- Updated
- 2022/05/15
- Product number
- CS-0091484
- Product name
- 1,3-Dimethyl-1H-benzimidazolium iodide
- Purity
- ≥97.0%
- Packaging
- 100mg
- Price
- $24
- Updated
- 2021/12/16
- Product number
- CS-0091484
- Product name
- 1,3-Dimethyl-1H-benzimidazolium iodide
- Purity
- ≥97.0%
- Packaging
- 250mg
- Price
- $54
- Updated
- 2021/12/16
- Product number
- 3H33-H-X0
- Product name
- 1,3-Dimethyl-1H-benzimidazol-3-iumiodide
- Packaging
- 250mg
- Price
- $184
- Updated
- 2021/12/16
1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide Chemical Properties,Usage,Production
Uses
Catalyst for:
- Domino ring-opening redox amidation Knoevenagel condensation
- Intramolecular stereoselective protonation
- Grignard allylic substitution
- Acylation of alcohols
- Umpolung reactions
reaction suitability
reagent type: catalyst
Synthesis
51-17-2
74-88-4
7181-87-5
The general procedure for the synthesis of 1,3-dimethyl-1H-benzo[d]imidazol-3-ium iodide from benzimidazole and iodomethane was as follows: 1H-benzo[d]imidazole (1 g, 8.5 mmol), K2CO3 (1.18 g, 8.5 mmol), iodomethane (2.1 mL, 33 mmol), and acetonitrile (15 mL) were added sequentially to a 25 mL Schlenk tube. The reaction tube was sealed, evacuated and filled with nitrogen three times to displace the air. The mixture was placed in a preheated 83°C oil bath, stirred and heated for 18 hours. Upon completion of the reaction, the reaction mixture was rapidly filtered while hot to remove insoluble material (immediate precipitation of white product was observed). The filtrate was quickly transferred to an ice water bath for cooling to induce the precipitation of white crystals. The crystals were collected by filtration, washed with petroleum ether (PE) and finally dried under reduced pressure to afford the target compound 1,3-dimethyl-1H-benzo[d]imidazol-3-ium iodide (NHC precursor J, 1.3 g, 56% yield).
References
[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8608 - 8618
[2] Organometallics, 2013, vol. 32, # 6, p. 2033 - 2036
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3646 - 3655
[4] Dalton Transactions, 2014, vol. 43, # 16, p. 5978 - 5982
[5] Organic Letters, 2007, vol. 9, # 17, p. 3437 - 3439
1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide Preparation Products And Raw materials
Raw materials
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