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(N,N-Dimethyl)methyleneammonium iodide, 97%, Thermo Scientific Chemicals
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Catalog number A15146.09
also known as A15146-09
Price (USD)/ Each
87.65
Online exclusive
96.90 Save 9.25 (10%)
-
Quantity:
10 g
Price (USD)/ Each
87.65
Online exclusive
96.90 Save 9.25 (10%)
(N,N-Dimethyl)methyleneammonium iodide, 97%, Thermo Scientific Chemicals
Catalog numberA15146.09
Price (USD)/ Each
87.65
Online exclusive
96.90 Save 9.25 (10%)
-
Chemical Identifiers
CAS33797-51-2
IUPAC Name(dimethylamino)methylium iodide
Molecular FormulaC3H8IN
InChI KeyVVDUZZGYBOWDSQ-UHFFFAOYSA-M
SMILES[I-].CN(C)[CH2+]
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Pale yellow to yellow or pale orange or cream to brown
FormCrystals or powder or crystalline powder
Assay (Titration ex Iodide)≥96.0 to ≤104.0%
(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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
(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.
Solubility
Soluble in dimethylformamide. Partially soluble in acetonitrile, tetrahydrofuran and dichloromethane.
Notes
Moisture and light sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place.
(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.
Solubility
Soluble in dimethylformamide. Partially soluble in acetonitrile, tetrahydrofuran and dichloromethane.
Notes
Moisture and light sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place.
RUO – Research Use Only
General 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).
- Cesario, C.; Miller, M. J. Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser’s salt: one-pot preparation of diverse carbocyclic scaffolds. Tetrahedron Lett. 2010, 51 (23), 3050-3052.
- Yamada, K.; Masaki, K.; Hagimoto, Y.; Kamiya, S.; Kunishima, M. A new method using 2-chloro-4,6-dimethoxy-1,3,5-triazine for facile elimination of dimethylamino group in Eschenmoser’s methylenation for synthesis of alpha,beta-unsaturated esters. Tetrahedron Lett. 2013, 54 (13), 1758-1760.