(N,N-Dimethyl)methyleneammonium iodide

• Catalog No.: A15146
• CAS Number: 33797-51-2
• M. F.: C3H8IN
• M. W.: 185.00679
• Purity: 97%

SYNONYMS

• Title: (N,N-二甲基)亚甲基碘化铵
• IUPAC name: dimethyl(methylidene)azanium iodide
• IUPAC Traditional name: dimethyl(methylidene)azanium iodide
• Synonyms: N,N-Dimethylmethyleneiminium iodide; Eschenmoser's iodide salt

DATABASE IDS

• Beilstein Number: 3594966
• MDL Number: MFCD00011810
• CAS Number: 33797-51-2
• EC Number: 251-680-2
• Merck Index: 143251

PROPERTIES

• Purity: 97%
• Melting Point: ca 240°C dec.
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Moisture & Light Sensitive
• TSCA Listed: 否

REFERENCES

• Crystalline salt of the Mannich intermediate, used by Eschenmoser to introduce a dimethylaminomethyl group into the corrin nucleus: Angew. Chem. Int. Ed., 10, 330 (1971). Enolates of ketones, esters and lactones give the Mannich bases from which the ɑ-methylene derivatives can be prepared by quaternization and elimination: Tetrahedron Lett., 1621 (1977). Malonate esters are converted to ɑ-substituted acrylates: J. Am. Chem. Soc., 104, 6787 (1982); 108, 8068 (1986); J. Chem. Soc., Chem. Commun., 480 (1989).
• The dimethylaminomethylenation of phenols gives high yields and shows a high ortho-regioselectivity: Synthesis, 906 (1983). Indoles are converted almost quantitatively to their 3-dimethylaminomethyl derivatives: Heterocycles, 14, 55 (1980).