Tetrakis(dimethylamino)ethylene

Base Information

• Chemical Name: Tetrakis(dimethylamino)ethylene
• CAS No.: 996-70-3
• Molecular Formula: C10H24 N4
• Molecular Weight: 200.327
• Hs Code.: 2921290000
• European Community (EC) Number: 213-638-1
• UNII: P6737B68MN
• DSSTox Substance ID: DTXSID0061371
• Nikkaji Number: J1.230.447A,J209.047C
• Wikipedia: Tetrakis(dimethylamino)ethylene
• Wikidata: Q3546869
• Mol file: 996-70-3.mol

Synonyms:TDAE cpd;tetrakis(dimethylamino)ethylene

Chemical Property of Tetrakis(dimethylamino)ethylene

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Melting Point: >200 °C (decomp)
• Refractive Index: n20/D 1.48(lit.)
• Boiling Point: 227.1 °C at 760 mmHg
• PKA: 6.47±0.70(Predicted)
• Flash Point: 53 ºC
• PSA: 12.96000
• Density: 0.861
• LogP: 0.35940
• Storage Temp.: 0-10°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 200.20009678
• Heavy Atom Count: 14
• Complexity: 162

Purity/Quality:

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

Tetrakis(dimethylamino)ethylene(>85%) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-27-36/37/39-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aliphatic
• Canonical SMILES: CN(C)C(=C(N(C)C)N(C)C)N(C)C
• Uses: Involved in TDAE methodology for coupling and intramolecular Buchwald reactionsActs as a reducing agentReactant involved in:DioxygenationInsertion of aluminum anion into the C-N bondChemiluminescent reactions with oxygen

Technology Process of Tetrakis(dimethylamino)ethylene

There total 23 articles about Tetrakis(dimethylamino)ethylene 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: 73.0%

tris(dimethylamino)methane (5762-56-1) → Tetrakis(dimethylamino)ethylen (996-70-3)

Guidance literature:

at 180 - 190 ℃; for 72h; Inert atmosphere;

DOI:10.3762/bjoc.5.1

Reference yield: 57.0%

N,N,N',N'-Tetramethylformamidinium chloride (1071-38-1) → Tetrakis(dimethylamino)ethylen (996-70-3) + isopropyltriphenylphosphonium chloride (35171-77-8)

Guidance literature:

With triphenylphosphonio-1-methylethanide; In benzene;

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + dimethyl amine (124-40-3) + tetramethylurea (632-22-4) + trichloromethyl chloroformate (503-38-8) → Tetrakis(dimethylamino)ethylen (996-70-3) + Tris(dimethylamino)methoxy-ethylen (36555-00-7) + tris(dimethylamino)methane (5762-56-1)

Guidance literature:

dimethyl amine; tetramethylurea; trichloromethyl chloroformate; In tetrahydrofuran; at 20 ℃;

Trimethyl borate; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h; Title compound not separated from byproducts;

upstream raw materials:

Chlorotrifluoroethylene

dimethyl amine

N,N,N',N'-Tetramethylformamidinium chloride

N,N,N',N'-tetramethylchlorformamidinium chloride

Downstream raw materials:

SbF₅^(1-)

SnCl₄^(1-)

1-methanesulfonyl-5-methoxy-3-vinyl-2,3-dihydro-1H-indole

diphenyldisulfane

Refernces

• 1、 Suzuki, Naoyuki,Hofstra, Julie L.,Poremba, Kelsey E.,Reisman, Sarah E.. "Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides". supporting information. p. 2150 - 2153. Retrieved 2017/04/27.
• 2、 Kantlehner, Willi,Stieglitz, Ruediger,Hauber, Michael,Haug, Erwin,Regele, Claudia. "Orthoamides. LII. Contributions to the synthesis of carboxylic ortho acid amides". . p. 256 - 268. Retrieved 2007/10/03.