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A15146 (N,N-Dimethyl)methyleneammonium iodide, 97%

CAS Number
33797-51-2
Synonyms
N,N-Dimethylmethyleneiminium iodide
Eschenmoser's iodide salt

Stock No. Size Price ($) Quantity Availability
A15146-09 10g 70.70
A15146-18 50g 239.00
A15146-30 250g 1090.00
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(N,N-Dimethyl)methyleneammonium iodide, 97%

MDL
MFCD00011810
EINECS
251-680-2

Chemical Properties

Formula
C3H8IN
Formula Weight
185.01
Melting point
ca 240° dec.
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Light Sensitive.
Solubility
Soluble in dimethylformamide. Partially soluble in acetonitrile, tetrahydrofuran and dichloromethane.

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.

Notes

Moisture and light sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place.

Literature 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).

/n

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,3251
Beilstein
3594966
Harmonized Tariff Code
2925.29
TSCA
No

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