dimethyl(methylidene)azanium iodide

• ChemBase ID: 127300
• Molecular Formular: C3H8IN
• Molecular Mass: 185.00679
• Monoisotopic Mass: 184.97014726
• SMILES: C[N+](=C)C.[I-]
• Canonical SMILES: C[N+](=C)C.[I-]
• InChI: InChI=1S/C3H8N.HI/c1-4(2)3;/h1H2,2-3H3;1H/q+1;/p-1
• InChIKey: VVDUZZGYBOWDSQ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl(methylidene)azanium iodide
• IUPAC Traditional name: dimethyl(methylidene)azanium iodide
• Synonyms: Eschenmoser's salt; N,N-Dimethylmethyleneammonium iodide; Eschenmoser’s salt; N,N-Dimethylmethyleneiminium iodide; N,N-Dimethylmethyleneiminium iodide; Eschenmoser's iodide salt; (N,N-Dimethyl)methyleneammonium iodide; N,N-二甲基亚甲基碘化胺; Eschenmoser 盐; N,N-二甲基亚甲基碘化铵; (N,N-二甲基)亚甲基碘化铵

Database IDs

• CAS Number: 33797-51-2
• EC Number: 251-680-2
• MDL Number: MFCD00011810
• Beilstein Number: 3594966; 1731022
• Merck Index: 143251
• PubChem SID: 24865478; 162221621; 24852854
• PubChem CID: 2724133
• Chemspider ID: 2006292
• Wikipedia Title: Eschenmoser's_salt

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -3.7471042
• LogD (pH = 7.4): -3.7471042
• Log P: -3.7471042
• Molar Refractivity: 29.3724 cm^3
• Polarizability: 7.276546 Å^3
• Polar Surface Area: 3.01 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: decomp. in water
• Apperance: colorless hygroscopic crystals
• Melting Point: 116°C; 219 °C (dec.)(lit.); 235-240 °C (dec.); ca 240°C dec.

Safety Information

• Storage Warning: Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R36/37/38
• Safety Statements: 26-36; 26-37; S26 S36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (AT); 97%; 98%
• Grade: purum
• Linear Formula: CH2=N+(CH3)2I-

DETAILS

Sigma Aldrich - 214914

Packaging
10, 50 g in glass bottle
Application
Useful reagent for many synthetic applications,1,2 especially aminomethylation;3,4 conversion of ketones to α,β-unsaturated enones.5

Sigma Aldrich - 40769

Other Notes
"Mannich-reagent" for direct use1,2,3,4: α-methylenation of carbonyls and ene reactions with olefins

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).