ESCHENMOSER'S SALT

Base Information

• Chemical Name: ESCHENMOSER'S SALT
• CAS No.: 33797-51-2
• Molecular Formula: C3H8 N . I
• Molecular Weight: 185.008
• Hs Code.: 29239000
• European Community (EC) Number: 251-680-2
• UNII: 5C42I004S1
• DSSTox Substance ID: DTXSID10369115
• Wikipedia: Eschenmoser%27s_salt,Eschenmoser's_salt
• Wikidata: Q414308
• Mol file: 33797-51-2.mol

Synonyms:Ammonium,dimethylmethylene-, iodide (8CI); Dimethyl(methylene)ammonium iodide;Eschenmoser's reagent; Eschenmoser's salt; Methylenedimethylammonium iodide;N,N-Dimethylaminomethyleneammonium iodide; N,N-Dimethylmethyleneiminium iodide

Chemical Property of ESCHENMOSER'S SALT

Chemical Property:

• Appearance/Colour: CREAM TO YELLOW CRYSTALLINE POWDER
• Melting Point: 219 °C (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 3.01000
• Density: g/cm³
• LogP: -3.03690
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Soluble in dimethylformamide. Partially soluble in acetonitrile,
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 184.97015
• Heavy Atom Count: 5
• Complexity: 26.3

Purity/Quality:

98%,99%, ^*data from raw suppliers

N,N-Dimethylmethyleneiminium iodide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C[N+](=C)C.[I-]
• Uses: In organic synthesis. (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.

Technology Process of ESCHENMOSER'S SALT

There total 11 articles about ESCHENMOSER'S SALT which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

bis-(dimethylamino)methane (51-80-9) → eschenmoser's salt (33797-51-2)

Guidance literature:

With 2-methyl-but-2-ene; trimethylsilyl iodide; In diethyl ether; at 0 ℃; for 0.333333h;

DOI:10.1021/jo01291a032

Reference yield: 96.0%

trimethylsilyl iodide (16029-98-4) + N-<(trimethylsiloxy)methyl>dimethylamine (80202-60-4) → Hexamethyldisiloxane (107-46-0) + eschenmoser's salt (33797-51-2)

Guidance literature:

In diethyl ether; at 20 ℃; for 1h;

Reference yield: 82.0%

Chloroiodomethane (593-71-5) + bis-(dimethylamino)methane (51-80-9) → eschenmoser's salt (33797-51-2)

Guidance literature:

for 72h;

DOI:10.1246/bcsj.55.534

upstream raw materials:

N,N-dimethyl(methylene)ammonium chloride

methyl iodide

Chloroiodomethane

bis-(dimethylamino)methane

Downstream raw materials:

2-dimethylaminomethyl-1-phenyl-butan-1-one

2-dimethylaminomethyl-1-phenyl-octan-1-one

1-Phenyl-2-dimethylaminomethyl-1-nonanon

N,N-Dimethyl-phenylselenomethylamin

Refernces

• 1、 Fletcher, Michelle O.,Zhang, Li,Vu, Quyen,Dolbier Jr., William R.. "Kinetic evidence for a novel, Grob-like substitution/fragmentation mechanism for the reaction of nucleophiles with trialkylammoniomethyl halides". . p. 1187 - 1192. Retrieved 1999.
• 2、 Fabre, Jean-Marc,Garin, Javier,Uriel, Santiago. "The synthesis of primary, secondary and tertiary aminomethyltetrathiafulvalenes". . p. 3983 - 3990. Retrieved 2007/10/02.