3947-77-1

Basic information

• Product Name: 2-Methylisoquinoliniumiodide
• Synonyms: 2-Methylisoquinoline-2-ium·iodide;2-methylisoquinolin-2-ium:iodide
• CAS NO: 3947-77-1
• Molecular Formula: C₁₀H₁₀N*I
• Molecular Weight: 271.10
• Mol File: 3947-77-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Methylisoquinoliniumiodide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylisoquinoliniumiodide(3947-77-1)
• EPA Substance Registry System: 2-Methylisoquinoliniumiodide(3947-77-1)

Safety Data

• Hazardous Substances Data: 3947-77-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Methylisoquinolinium iodide is used as a reagent for its strong nucleophilic nature, which aids in the synthesis of functionalized molecules. It is particularly effective in the creation of complex organic structures that are integral to the development of new pharmaceuticals and natural product analogs.
Used in Catalysis:
In the field of catalysis, 2-Methylisoquinolinium iodide is employed as a catalyst to enhance the efficiency of various transformation and coupling reactions. Its application accelerates the synthesis process, making it a valuable tool in the production of a wide array of organic compounds.
Used in Pharmaceutical Industry:
2-Methylisoquinolinium iodide is used as a catalyst in the synthesis of pharmaceuticals for its ability to facilitate complex organic reactions, thereby contributing to the development of novel drugs and therapeutic agents.
Used in Academic Research:
In academic research, 2-Methylisoquinolinium iodide is utilized as a catalyst to explore new reaction pathways and mechanisms, furthering the understanding of organic chemistry and its applications in various scientific disciplines.

InChI:InChI=1/C10H10N/c1-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3/q+1

Upstream product

• 119-65-3 isoquinoline 
• 74-88-4 methyl iodide 
• 1126-71-2 N,N-dimethylphenethylamine 
• 14761-82-1 2-(2-dimethylaminomethylphenyl)ethanol 
• 14761-78-5 2-<2-Dimethylamino-aethyl>-benzylalkohol 
• 103-83-3 N,N'-dimethylbenzylamine 
• 1637-45-2 2,2-dimethyl-1,2,3,4-tetrahydroisoquinolinium iodide 

Downstream Products

• 581-89-5 2-nitronaphthalene 
• 24516-67-4 6,15-dimethyl-7-nitro-5,6,6a,7,8,13,14,14a-octahydro-5,13-cyclo-8,14-epimino-benzo[5,6]cycloocta[1,2-c]isoquinoline 
• 16620-95-4 1-(4,5-dimethoxy-2-nitro-benzyl)-2-methyl-1,2-dihydro-isoquinoline 
• 14990-40-0 N-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1612-65-3 2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 131792-46-6 1-<4-(benzyloxy)-5-methoxy-2-nitrobenzal>-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 131792-49-9 1-<5-(benzyloxy)-4-methoxy-2-nitrobenzal>-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 491-34-9 N-methyl-1,2,3,4-tetrahydroquinoline 
• 87993-10-0 N-Methyl-N-benzyl-1,2,3,4-tetrahydroisochinoliniumiodid 
• 123648-13-5 2-methyl-1-phenyl-1,2-dihydroisoquinoline 
• 28102-51-4 1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinoline 
• 93405-92-6 4-Benzyl-1,2,3,4-tetrahydro-N-methyl-isochinolin 
• 21640-33-5 2-methyl-isoquinoline-1,3,4-trione 
• 6772-65-2 2-methyl-3,4-dihydro-2H-isoquinolin-1-one 

Relevant articles and documents

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts

The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.

Regioselective Direct C-H Trifluoromethylation of Pyridine

A highly efficient and regioselective direct C-H trifluoromethylation of pyridine based on an N-methylpyridine quaternary ammonium activation strategy has been developed. A variety of trifluoromethylpyridines can be obtained in good yield and excellent re

Electrochemical regioselective selenylation/oxidation of: N-alkylisoquinolinium salts via double C(sp2)-H bond functionalization

An efficient, novel, and environmentally friendly electrochemical regioselective selenylation/oxidation of N-alkylisoquinolinium salts via double C(sp2)-H bond functionalization under undivided electrolytic conditions has been developed. A series of selenide isoquinolones were easily accessed through this sustainable and clean electrochemical system. The present protocol was further extended to afford selenide quinolones and 1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-ones. Furthermore, antiviral bioassays demonstrated that compound 3j exhibited excellent antiviral activity against tobacco mosaic virus (TMV), and its inhibition rate was up to 90%. This journal is

Synthesis of 4-Iodoisoquinolin-1(2 H)-ones by a Dirhodium(II)-Catalyzed 1,4-Bisfunctionalization of Isoquinolinium Iodide Salts

An efficient Rh2(II,II)-catalyzed reaction has been developed under mild conditions. This synthetic method proceeds through iodination/oxidation of readily available isoquinolinium iodide salts under aerobic conditions with good to excellent yields. 4-Iodoisoquinolin-1(2H)-ones are important building blocks for biologically and medicinally important compounds. The developed methodology was applied to the gram-scale synthesis of a key intermediate in the synthesis of the CRTH2 antagonist CRA-680.

Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.

Construction of Tropane Derivatives by the Organocatalytic Asymmetric Dearomatization of Isoquinolines

A chiral-NHC-catalyzed highly diastereo- and enantioselective dearomatizing double Mannich reaction of isoquinolines was developed that provides a powerful and straightforward synthetic route toward substituted tropane derivatives with four contiguous ste

Cucurbit[7]uril complexations of bis(isoquinolinium)alkane dications in aqueous solution

The 1:1 and 2:1 host-guest complexation of a series of 1,n- bis(isoquinolinium)alkane dications (Iq(CH2)nIq 2+, n = 2, 4, 5, 6, 8, 9, 10 and 12, and Iq(p-xylene)Iq2+) by cucurbit[7]uril (CB[7]) in aqueous solution has been investigated by 1H NMR spectroscopy and ESI mass spectrometry. The site of binding of the first CB[7] is dependent on the nature of the central linker group, with encapsulation of the p-xylene group or the polymethylene chain when n = 6-10.With shorter (n = 2-5) or longer (n = 12) chains, the first CB[7] binds over an isoquinolinium group. With a second CB[7], the binding of the central group is abandoned in favour of the CB[7] hosts encapsulating the two cationic isoquinolinium termini. The 1:1 and 2:1 host-guest stability constants are related to modes of binding and the nature of the central linkers, and are compared with dicationic guests bearing different terminal groups.

Synthesis of CF3-substituted 1,2,3,4-tetrahydroisoquinolines and 1,2,3,6-tetrahydropyridines

A three-step method for the preparation of CF3-substituted 1,2,3,4-tetrahydroisoquino-lines and 1,2,3,6-tetrahydropyridines has been suggested. The first step includes alkylation of isoquinoline or 4-methylpyridine at the nitrogen atom with the

Efficient macrocyclization achieved via conformational control using intermolecular noncovalent π-cation/arene interactions

Quinolinium salt 3 is an effective additive that acts as a conformation control element (CCE) to promote macrocyclization to form rigid cyclophanes via olefin metathesis or Glaser-Hay coupling, which do not cyclize in the absence of the additive. The additives are easily synthesized and highly modifiable and have solubility profiles which allow for simple recovery via filtration.