N,N-DiMethylMethyleneaMMoniuM Iodide

N,N-DiMethylMethyleneaMMoniuM Iodide Basic information
Product Name:N,N-DiMethylMethyleneaMMoniuM Iodide
Synonyms:ESCHENMOSER'S SALT;DIMETHYL METHYLENE AMMONIUM IODIDE;DIMETHYL METHYLENEIMMONIUM IODIDE;N,N-DIMETHYLMETHYLENEAMMONIUM IODIDE;N,N-DIMETHYLMETHYLENEIMINIUM IODIDE;Dimethyl methyleneammonium iodide~Eschenmosers iodide salt;(N,N-Dimethyl)methyleneammoniumiodide,97%;dimethylmethylammonium iodide
CAS:33797-51-2
MF:C3H8IN
MW:185.01
EINECS:251-680-2
Product Categories:Ammonium Iodides (Quaternary);Quaternary Ammonium Compounds
Mol File:33797-51-2.mol
N,N-DiMethylMethyleneaMMoniuM Iodide Structure
N,N-DiMethylMethyleneaMMoniuM Iodide Chemical Properties
Melting point 219 °C (dec.)(lit.)
density 1.7217 (estimate)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility Soluble in dimethylformamide. Partially soluble in acetonitrile, tetrahydrofuran and dichloromethane.
form Crystalline Powder
color Cream to yellow
Sensitive Moisture & Light Sensitive
Merck 14,3251
BRN 3594966
CAS DataBase Reference33797-51-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
8-10-21
HS Code 29239000
MSDS Information
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ACROS English
SigmaAldrich English
ALFA English
N,N-DiMethylMethyleneaMMoniuM Iodide Usage And Synthesis
Chemical PropertiesCREAM TO YELLOW CRYSTALLINE POWDER
UsesIn organic synthesis.
Uses(N,N-Dimethyl)methyleneammonium iodide is a useful reagent for many synthetic applications like aminomethylation. It is also essential for the conversion of ketones to α, β-unsaturated enones. It is utilized to prepare derivatives of the type RCH2N(CH3)2. It is extensively used in medicines like painkillers and sedatives- Tramadol hydrochloride intermediate viz. 2-dimethylamine methylcyclohexanone. It is also employed in reactive dyes, synthesized spices. It plays an essential role in Mannich reactions.
General DescriptionN,N-Dimethylmethyleneiminium iodide is useful reagent for many synthetic applications, especially aminomethylation and conversion of ketones to α,β?unsaturated enones.
SynthesisThe mixture of trimethylamine, diiodomethane, dioxane and absolute ethanol was placed in the dark to react at room temperature for 100 h, the resulting crystals were collected by filtration, washed with ethanol and ether in turn, and dried under vacuum at 70 °C to obtain iodomethyl trimethylMethylammonium iodide. It was heated with sulfolane and kept at 160 °C for 12 min. The precipitated crystals were collected by filtration, washed with carbon tetrachloride, and vacuum dried at 50 °C to obtain N,N-DiMethylMethyleneaMMoniuM Iodide.
5-METHOXY-2-(3-(5-METHOXY-1,3,3-TRIMETHYL-1H -2(3H)-INDOLIDENE)-1-PROPENYL)- 1,3,3-TRIMETHYL-3H-INDOLIUM IODIDE 2,3-DIMETHYLTHIAZOLINIUM IODIDE N-(([ANILINO(METHYLSULFANYL)METHYLENE]AMINO)METHYLENE)-N-METHYLMETHANAMINIUM IODIDE 2-(BETA-ANILINO)VINYL-3-ETHYL THIAZOLIUM IODIDE 2-(BETA-ANILINO)VINYL-3-METHYL THIAZOLIUM IODIDE 3-ETHYL-2-METHYL-2-THIAZOLINIUM IODIDE, 98 N,N'-DICYCLOHEXYLCARBODIIMIDE METHIODIDE N,N-DiMethylMethyleneaMMoniuM Iodide Hexacyanine 2 1,3,3-TRIMETHYL-5-PHENYL-2-(7-(1,3,3-TRIMETHYL-5-PHENYL-1H-2(3H)-INDOLIDENE)-1,3,5-HEPTATRIENYL)-3H-INDOLIUM IODIDE, 4-TOLUENESULFONATE N-(([(4-METHOXYANILINO)(METHYLSULFANYL)METHYLENE]AMINO)METHYLENE)-N-METHYLMETHANAMINIUM IODIDE 1,1',3,3,3',3'-HEXAMETHYLINDOTRICARBOCYANINE IODIDE N-(([(2-FLUOROANILINO)(METHYLSULFANYL)METHYLENE]AMINO)METHYLENE)-N-METHYLMETHANAMINIUM IODIDE N-(([(4-CHLOROANILINO)(METHYLSULFANYL)METHYLENE]AMINO)METHYLENE)-N-METHYLMETHANAMINIUM IODIDE 1,1,3-TRIMETHYL-2-(7-(1,1,3-TRIMETHYL-1H-2(3H)-BENZINDOLIDENE)-1,3,5- HEPTATRIENYL)-1H-BENZINDOLIUM IODIDE 1-(P-TOSYL)-3,4,4-TRIMETHYL-2-IMIDAZOLINIUM IODIDE 2-(2-(3,4-DIMETHOXYPHENYL)ETHENYL)-1,3,3,5,6-PENTAMETHYL-3H-INDOLIUM IODIDE 1,2,3,3-Tetramethyl-3H-indolium iodide

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