996-70-3

Basic information

• Product Name: TETRAKIS(DIMETHYLAMINO)ETHYLENE
• Synonyms: TETRAKIS(DIMETHYLAMINO)ETHYLENE;TDAE;OCTAMETHYL-ETHYLENETETRAMINE;Ethenetetramine, octamethyl-;octamethyl-ethenetetramin;LABOTEST-BB LT00455105;N,N',N'',N'''-tetramethylethylenediylidenetetraamine;Tetrakis(dimethylamino)ethylene,97%
• CAS NO: 996-70-3
• Molecular Formula: C₁₀H₂₄N₄
• Molecular Weight: 200.32
• EINECS: 213-638-1
• Product Categories: Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials
• Mol File: 996-70-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: >200 °C (decomp)
• Boiling Point: 98°C 25mm
• Flash Point: 53°C
• Appearance: clear yellow liquid
• Density: 0.861 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.48(lit.)
• Storage Temp.: 0-10°C
• PKA: 6.47±0.70(Predicted)
• Stability: Stable. Incompatible with acid chlorides, acids, strong oxidizing agents, acid anhydrides, carbon dioxide, oxygen, chlorinated s
• BRN: 1705900
• CAS DataBase Reference: TETRAKIS(DIMETHYLAMINO)ETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAKIS(DIMETHYLAMINO)ETHYLENE(996-70-3)
• EPA Substance Registry System: TETRAKIS(DIMETHYLAMINO)ETHYLENE(996-70-3)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-27-36/37/39-45-26
• RIDADR: 3286
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 996-70-3(Hazardous Substances Data)

Usage

Chemical Properties

light yellow-green liquid with an unpleasant

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

Purification Methods

Impurities include tetramethylurea, dimethylamine, tetramethylethanediamine and tetramethyloxamide. It is washed with water while being flushed with nitrogen to remove dimethylamine, dried over molecular sieves, then passed through a silica gel column (previously activated at 400o) under nitrogen. De-gas it in a vacuum line by distillation from a trap at 50o to one at -70o. Finally, it is stirred over sodium-potassium alloy for several days. [Holroyd et al. J Phys Chem 89 4244 1985, Wiberg Angew Chem Int Ed Engl 7 766 1968, Beilstein 4 IV 167.]

Upstream product

• 7646-78-8 tin(IV) chloride 
• 7783-70-2 antimony pentafluoride 
• 121-43-7 Trimethyl borate 
• 124-40-3 dimethyl amine 
• 632-22-4 tetramethylurea 
• 503-38-8 trichloromethyl chloroformate 
• 1071-38-1 N,N,N',N'-Tetramethylformamidinium chloride 
• 56043-45-9 N,N,N',N'-tetramethylchlorformamidinium chloride 
• 79-38-9 Chlorotrifluoroethylene 
• 5762-56-1 tris(dimethylamino)methane 

Downstream Products

• 116122-92-0 SbF₅^(1-) 
• 69192-36-5 SnCl₄^(1-) 
• 1137520-82-1 1-methanesulfonyl-5-methoxy-3-vinyl-2,3-dihydro-1H-indole 
• 882-33-7 diphenyldisulfane 
• 108485-48-9 C₂(N(CH₃)2)4BH₂⁽¹⁺⁾*B(C₆H₅)4^(1-)={(C₂(N(CH₃)2)4)BH₂}B(C₆H₅)4 
• 632-22-4 tetramethylurea 
• 6415-13-0 N,N,N',N',N'',N'',N''',N'''-Octamethyl-oxamidiniumdibromid 

Relevant articles and documents

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals

Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derived from arenediazonium salts are also reported. The relative ease of removal of the oxidized by-products of TDAE from the reaction mixture makes the methodology synthetically attractive.

Linear free-energy relationship for electron-transfer processes of pyrrolidinofullerenes with tetrakis(dimethylamino)ethylene in ground and excited states

Systematic studies of electron-transfer processes in the ground states and excited triplet states of pyrrolidinofullerenes {C60(C3H6N)R [R = H (1), p-C6H4NO2 (2), p-C6H4CHO (3), p-C6H5 (4), p-C6H4Me (5), p- C6H4NMe2 (6)]} with tetrakis(dimethylamino)ethylene (TDAE) have been carried out by steady-state and transient absorption measurements in the visible-NIR region. Analyses of the equilibria of the electron-transfer processes in the ground states indicate that free ion radicals are produced in polar solvents. Photoinduced electron-transfer processes via (T)(C60(C3H6N)R)* were observed by applying a perturbation to the equilibria of the electron-transfer reactions in the ground states by laser flash photolysis. Based on the relationship of the thermodynamic data and kinetic data, the electron-transfer rate constants in the ground states (k(et)/(G)) can be evaluated. The k(et)/(G) values are affected by the substituents to a smaller extent compared with the equilibrium constants (K) in polar solvents; α = 0.6 in Δ log k(et)/(G) = α Δ log K. This α value indicates that the activation energies of forward electron transfer in the ground states vary moderately with the thermodynamic stabilities of (C60(C3H6N)R).-. Electron-transfer rate constants via (T)(C60(C3H6N)R)* which are close to the diffusion-controlled limit, do not show a large substituent effect (α = 0), because of their highly exothermic processes. Such a linear free-energy relationship can be extended to other systems such as (T)(C60(C3H6N)R)*/N,N-dimethylaniline, from which valuable information for electron-transfer processes can be obtained.